Acids And Bases Chapter.3 Exam Questions - Organic Chemistry 4e | Test Bank by Klein by David R. Klein. DOCX document preview.

Acids And Bases Chapter.3 Exam Questions

Organic Chemistry, 4e (Klein)

Chapter 3 Acids and Bases

1) A Brønsted-Lowry acid is defined as a ________.

A) proton acceptor

B) proton donor

C) species remaining after acid is deprotonated

D) species remaining after base is protonated

E) species that can react with water

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

2) A Brønsted-Lowry base is defined as a ________.

A) proton acceptor

B) proton donor

C) species remaining after acid is deprotonated

D) species remaining after base is protonated

E) species that can react with water

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

3) A conjugate acid is defined as a ________.

A) proton acceptor

B) proton donor

C) species remaining after acid is deprotonated

D) species remaining after base is protonated

E) species that can react with water

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

4) A conjugate base is defined as a ________.

A) proton acceptor

B) proton donor

C) species remaining after acid is deprotonated

D) species remaining after base is protonated

E) species that can react with water

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

5) For the following reaction, identify the Brønsted-Lowry base and the conjugate acid.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

6) For the following reaction, identify the Brønsted-Lowry acid and the conjugate acid.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

7) For the following reaction, identify the Brønsted-Lowry base and the corresponding conjugate base.

An illustration shows a chemical reaction. Compound 1, H 2 S O 4 reacts with compound 2 that has a SMILES string of CCOCC to yield compound 3 and compound 4. The structure of compound 3 has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to two ethyl groups. The compound 4 has a SMILES string of OS(=O)(=O)[O-].

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

8) For the following reaction, identify the Brønsted-Lowry acid and the conjugate base.

An illustration shows a chemical reaction. Compound 1, H 2 S O 4 reacts with compound 2 that has a SMILES string of CCOCC to yield compound 3 and compound 4. The structure of compound 3 has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to two ethyl groups. The compound 4 has a SMILES string of OS(=O)(=O)[O-].

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

9) For the following reaction, identify the Brønsted-Lowry base and the conjugate base.

An illustration shows a chemical reaction. Compound 1, H C l reacts with compound 2 that has a SMILES string of CCO to yield compound 3 and compound 4. The structure of compound 3 has a two-carbon chain, in which C 1 is bonded to an oxygen atom carrying a positive charge and the oxygen atom is bonded to two hydrogen atoms. The compound 4 formed is chloride ion, C l superscript negative.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

10) Which of the following is not a Brønsted-Lowry acid?

A) CH3OH

B) CBr4

C) HCl

D) CH3SH

E) H2O

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

11) Which of the following is not a Brønsted-Lowry base?

A) CH3OH

B) CH3OCH3

C) CH3NH2

D) CH3CH3

E) CH3SH

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

12) In a Brønsted-Lowry acid-base reaction, the acid is defined as ________.

A) a proton acceptor

B) a proton donor

C) the product resulting from loss of a proton

D) the product resulting from gaining a proton

E) the most reactive species

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

13) In a Brønsted-Lowry acid-base reaction, the base is defined as ________.

A) a proton acceptor

B) a proton donor

C) the product resulting from loss of a proton

D) the product resulting from gaining a proton

E) the most reactive species

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

14) Which of the following is always formed from the loss of proton from a Brønsted-Lowry acid?

A) a Lewis acid

B) a conjugate acid

C) a conjugate base

D) a species with a negative charge

E) a neutral solution

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

15) Which of the following is always formed from the gain of proton by a Brønsted-Lowry base?

A) a Lewis base

B) a conjugate acid

C) a conjugate base

D) a species with a positive charge

E) a neutral solution

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

16) Identify the conjugate base of nitric acid, HNO3.

A) NO3—

B) NO2—

C) HNO3

D) HNO2

E) H2NO3+

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

17) Identify the conjugate base of phosphoric acid, H3PO4.

A) HPO42—

B) H2PO4—

C) HPO32—

D) PO43—

E) H2PO3—

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

18) Identify the conjugate base of CH3CH2SH.

A) CH3CH2S—

B) CH3CH2—

C) CH3CH2SH2+

D) CH3CH2S2—

E) CH3CH2+

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

19) Identify the conjugate acid of CH3CH2OH.

An illustration depicts the structures of five compounds. The structures are as follows: 
Compound 1: C H 3 C H 2 O, in which the oxygen atom carries a negative charge.
Compound 2: C H 3 C H 2 O H 2, in which the oxygen atom carries a positive charge.
Compound 3: C H 3 C H O H, in which the carbon atom carries a positive charge.
Compound 4: a central carbon atom single bonded to a methyl group, to a hydrogen atom, and double bonded to an oxygen atom carrying a positive charge and the oxygen atom is bonded to a hydrogen atom. 
Compound 5: C H 2 C H 2 O H, in which the terminal methylene carbon carries a lone pair of electrons and a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

20) Identify the conjugate acid of CH3-O-CH3.

An illustration depicts the structures of five compounds. The structures are as follows: 
Compound 1: C H 3 O C H 3, in which the oxygen atom carries a positive charge. 
Compound 2: C H 3 O C H 4, in which the carbon atom of the C H 4 group carries a positive charge. 
Compound 3: C H 3 O C H 3, in which the oxygen atom carries a negative charge.
Compound 4: a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to two methyl groups. 
Compound 5: C H 3 O, in which the oxygen atom carries a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

21) Identify the conjugate acid of the compound shown in the box below.

The bond-line structure of the compound has a SMILES string of CCC(=O)C.

An illustration depicts the bond-line structures of five compounds. 
Compound 1 has a SMILES string of CCC(C)O. 
Compound 2 has a SMILES string of CCC(=O)C, in which C 3 carries a positive charge. 
Compound 3 has a SMILES string of C/C=C(/C)\O. 
Compound 4 has a four-carbon chain, in which C 2 carries a positive charge and is single bonded to an oxygen atom carrying a negative charge. 
Compound 5 has a four-carbon chain, in which C 2 is double bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

22) Identify the conjugate base of CH3C≡CH.

An illustration depicts the structures of five compounds. The structures are as follows: 
Compound 1: a three-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is a methylene group. The methylene carbon carries a positive charge. 
Compound 2: a three-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 2 carries a negative charge, and C 3 is a methyl group. 
Compound 3: a three-carbon chain, in which C 1 carrying a negative charge is triple bonded to C 2 and C 3 is a methyl group. 
Compound 4: a three-carbon chain, in which C 1 carrying a positive charge is triple bonded to C 2 and C 3 is a methyl group.
Compound 5: a three-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is a methylene group. The methylene carbon carries a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

23) Identify the conjugate base of CH3CH2NH2.

An illustration depicts the structures of five compounds. The structures are as follows: 
Compound 1: C H 3 C H 3 N H 2, in which the nitrogen atom carries a negative charge. 
Compound 2: C H 3 C H 2 N H 3, in which the nitrogen atom carries a positive charge. 
Compound 3: C H 3 C H 2 N H 3, in which the nitrogen atom carries a negative charge. 
Compound 4: C H 2 C H 2 N H 2, in which the terminal methylene carbon carries a negative charge and a lone pair of electrons. 
Compound 5: C H 2 C H 2 N H 2, in which the terminal methylene carbon carries a positive charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

24) Identify the conjugate base of the compound shown in the box below.

The structure of the compound has a SMILES string of c1ccc(cc1)O.

An illustration shows the structures of five compounds. 
Compound 1 has a benzene ring, in which C 1 is bonded to a hydroxyl group and C 4 carries a negative charge. 
Compound 2 has a benzene ring, in which C 1 is bonded to an oxygen atom carrying a positive charge that is further bonded to two hydrogen atoms. 
Compound 3 has a benzene ring, in which C 1 is bonded to an oxygen atom carrying a negative charge. 
Compound 4 has a cyclohexane ring, in which C 3 is double bonded to C 4 and C 5 is double bonded to C 6. C 1 is double bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom. C 2 carries a negative charge. 
Compound 5 has a benzene ring, in which C 1 is bonded to an oxygen atom carrying a negative charge that is further bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

25) Identify the conjugate base of the compound shown in the box below.

The bond-line structure of the compound has a central carbon atom double bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom, single bonded to a hydroxyl group, and single bonded to a methyl group.

An illustration depicts the bond-line structures of five compounds. The structures are as follows: 
Compound 1 has a central carbon atom double bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom, single bonded to an oxygen atom carrying a negative charge, and single bonded to a methyl group. 
Compound 2 has a central carbon atom double bonded to an oxygen atom, single bonded to an oxygen atom carrying a negative charge, and single bonded to a methyl group. 
Compound 3 has a central carbon atom double bonded to an oxygen atom, single bonded to an oxygen atom carrying a positive charge that is further bonded to two hydrogen atoms, and single bonded to a methyl group. 
Compound 4 has a central carbon atom double bonded to an oxygen atom, single bonded to a hydroxyl group, and single bonded to a methyl group. 
Compound 5 has a central carbon atom carrying a positive charge is single bonded to two hydroxyl groups and single bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

26) For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate base.

An illustration shows a chemical reaction. Compound 1, C H 3 C H 2 C H 2 O H 2, in which the oxygen atom carries a positive charge reacts with compound 2, H 2 O to yield compound 3, C H 3 C H 2 C H 2 O H and compound 4, hydronium ion, H 3 O superscript positive.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

27) For the following reaction, respectively identify the Brønsted-Lowry base and the conjugate acid.

An illustration shows a chemical reaction. Compound 1, C H 3 C H 2 C H 2 O H 2, in which the oxygen atom carries a positive charge reacts with compound 2, H 2 O to yield compound 3, C H 3 C H 2 C H 2 O H and compound 4, hydronium ion, H 3 O superscript positive.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

28) For the following reaction, respectively identify the Brønsted-Lowry acid and the conjugate base.

An illustration shows a chemical reaction. Compound 1, C H 3 C H 2 C H 2 O H 2, in which the oxygen atom carries a positive charge reacts with compound 2, H 2 O to yield compound 3, C H 3 C H 2 C H 2 O H and compound 4, hydronium ion, H 3 O superscript positive.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

29) For the following reaction, respectively identify the Brønsted-Lowry acid and the conjugate acid.

An illustration shows a chemical reaction. Compound 1, C H 3 C H 2 C H 2 O H 2, in which the oxygen atom carries a positive charge reacts with compound 2, H 2 O to yield compound 3, C H 3 C H 2 C H 2 O H and compound 4, hydronium ion, H 3 O superscript positive.

A) I and II

B) I and III

C) I and IV

D) II and IIII

E) II and IV

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

30) For the following reaction identify the acid, base, conjugate acid and conjugate base.

An illustration shows a chemical reaction. Compound 1, C H 3 C H 2 S H reacts with compound 2, N a O H, in which the sodium cation carries a positive charge and the hydroxyl group carries a negative charge to yield compound 3 and compound 4. The structure of compound 3 is C H 3 C H 2 S N a, in which the sulfur atom carries a negative charge and the sodium atom carries positive charge. The compound 4 formed is a molecule of water, H 2 O.

A) I = base; II = acid; III = conjugate base; IV = conjugate acid

B) I = acid; II = base; III = conjugate base; IV = conjugate acid

C) I = base; II = acid; III = conjugate acid; IV = conjugate base

D) I = acid; II = base; III = conjugate acid; IV = conjugate base

E) I = base; II = base; III = conjugate acid; IV = conjugate acid

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

31) For the following reaction identify the acid, base, conjugate acid and conjugate base.

An illustration shows a chemical reaction. The reactant, C H 3 C H 2 L i, in which the methylene carbon carries a negative charge and the lithium atom carries a positive charge, reacts with another compound that has a central nitrogen atom carrying a positive charge is single bonded to two hydrogen atoms, to a methyl group, and to an ethyl group to yield three products. The first product has a SMILES string of CCNC. The second product is C H 3 C H 3. The third product is lithium cation, L i superscript positive.

A) I = base; II = acid; III = conjugate base; IV = conjugate acid

B) I = acid; II = base; III = conjugate base; IV = conjugate acid

C) I = base; II = acid; III = conjugate acid; IV = conjugate base

D) I = acid; II = base; III = conjugate acid; IV = conjugate base

E) I = base; II = base; III = conjugate acid; IV = conjugate acid

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

32) For the following reaction identify the acid, base, conjugate acid and conjugate base.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCC#C reacts with N a O H to yield two products. The first product is H 2 O. The second product has a four-carbon chain, in which C 1 carrying a positive charge is triple bonded to C 2. The compound is in association with sodium cation, N a superscript positive.

A) I = base; II = acid; III = conjugate base; IV = conjugate acid

B) I = acid; II = base; III = conjugate base; IV = conjugate acid

C) I = base; II = acid; III = conjugate acid; IV = conjugate base

D) I = acid; II = base; III = conjugate acid; IV = conjugate base

E) I = base; II = base; III = conjugate acid; IV = conjugate acid

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

33) The tail of the curved arrow must start at ________ electron density and the head must end at ________ electron density.

A) low, high

B) high, high

C) low, low

D) high, low

E) none of the above

Diff: 1

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

34) For the following acid-base reaction, identify the correct curved arrow mechanism.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCS reacts with N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge to yield two products. The first product has a two-carbon chain, in which C 1 is bonded to a sulfur atom carrying a negative charge and the compound is in association with sodium cation, N a superscript positive. The second product is H 2 O.

An illustration shows set of reactants for an incomplete partial reaction. 
Compound 1: The first reactant has a two-carbon chain, in which C 1 is bonded to an S H group. The second reactant is hydroxyl ion, O H superscript negative. A curved arrow from the single bond between S H points toward the sulfur atom and another curved arrow from the hydrogen atom of the S H group points toward the oxygen atom of the hydroxyl group. 
Compound 2: The first reactant has a two-carbon chain, in which C 1 is bonded to an S H group. The second reactant is hydroxyl ion, O H superscript negative. A curved arrow from the single bond between S H points toward the sulfur atom. A double headed arrow from the hydrogen atom of the S H group points toward the oxygen atom of the hydroxyl group and vice versa. 
Compound 3: The first reactant has a two-carbon chain, in which C 1 is bonded to an S H group. The second reactant is hydroxyl ion, O H superscript negative. A curved arrow from the sulfur atom of S H group points toward the single bond between S H and another curved arrow from the hydrogen atom of the S H group points toward the oxygen atom of the hydroxyl group. 
Compound 4: The first reactant has a two-carbon chain, in which C 1 is bonded to an S H group. The second reactant is hydroxyl ion, O H superscript negative. A curved arrow from the single bond between S H points toward the sulfur atom and another curved arrow from the oxygen atom of the hydroxyl group points toward the hydrogen atom of the S H group. 
Compound 5: The first reactant has a two-carbon chain, in which C 1 is bonded to an S H group. The second reactant is hydroxyl ion, O H superscript negative. A curved arrow from the sulfur atom of S H group points toward the single bond between S H and another curved arrow from the oxygen atom of the hydroxyl group points toward the hydrogen atom of the S H group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

35) For the following acid-base reaction, identify the correct curved arrow mechanism.

An illustration shows an incomplete reaction. The reactant that has a four-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group reacts with N a N H 3, in which the sodium atom carries a positive charge and the nitrogen atom of the N H 3 group carries a negative charge to yield two products. The first product has a four-carbon chain, in which C 1 carries a negative charge and is triple bonded to C 2, C 3 is bonded to a methyl group and the compound is in association with the sodium cation, N a superscript positive. The second product is N H 3.

An illustration shows set of reactants for an incomplete partial reaction.
Compound 1: The first reactant has a four-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group. The second reactant is N H 2, in which the nitrogen atom carries a negative charge. A curved arrow from the carbon-hydrogen single bond points toward the corresponding carbon atom and another curved arrow from the nitrogen atom of the N H 2 group points toward the hydrogen atom of the first reactant. 
Compound 2: The first reactant has a four-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group. The second reactant is N H 2, in which the nitrogen atom carries a negative charge. A curved arrow from the carbon-hydrogen single bond points toward the corresponding carbon atom and another curved arrow from the hydrogen atom of the first reactant points toward the nitrogen atom of the N H 2 group. 
Compound 3: The first reactant has a four-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group. The second reactant is N H 2, in which the nitrogen atom carries a negative charge. A curved arrow from the carbon-hydrogen single bond points toward the corresponding carbon atom and another curved arrow from the carbon-hydrogen single bond points toward the corresponding hydrogen atom. A third curved arrow from the nitrogen atom of the N H 2 group points toward the hydrogen atom of the first reactant.
Compound 4: The first reactant has a four-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group. The second reactant is N H 2, in which the nitrogen atom carries a negative charge. A curved arrow from the carbon-hydrogen single bond points toward the corresponding hydrogen atom and another curved arrow from the hydrogen atom of the first reactant points toward the nitrogen atom of the N H 2 group. 
Compound 5: The first reactant has a four-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group. The second reactant is N H 2, in which the nitrogen atom carries a negative charge. A curved arrow from the hydrogen atom of the first reactant points toward the nitrogen atom of the N H 2 group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

36) For the following acid-base reaction, identify the correct curved arrow mechanism.

An illustration shows a chemical reaction. The reactant that has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms reacts with another compound that has a two-carbon chain, in which C 1 is bonded to an N H 2 group to yield two products. The first product has a SMILES string of c1ccc(cc1)N and the second product has a SMILES string of CC[NH3+].

An illustration shows set of reactants for an incomplete partial reaction.
Compound 1: The first reactant has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms. The second reactant has a two-carbon chain, in which C 1 is bonded to an N H 2 group. A curved arrow from the nitrogen-hydrogen single bond of the N H 3 group points toward the corresponding hydrogen atom and another curved arrow from the hydrogen atom of the first reactant points toward the nitrogen atom of the N H 2 group on the second reactant. 
Compound 2: The first reactant has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms. The second reactant has a two-carbon chain, in which C 1 is bonded to an N H 2 group. A curved arrow from the nitrogen-hydrogen single bond of the N H 3 group points toward the corresponding nitrogen atom and another curved arrow from the nitrogen atom of the N H 2 group points toward the hydrogen atom on the first reactant. 
Compound 3: The first reactant has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms. The second reactant has a two-carbon chain, in which C 1 is bonded to an N H 2 group. A curved arrow from the nitrogen-hydrogen single bond of the N H 3 group points toward the corresponding hydrogen atom and another curved arrow from the nitrogen-hydrogen single bond of the N H 3 group points toward the corresponding nitrogen atom. A third curved arrow from the nitrogen atom of the N H 2 group points toward the hydrogen atom on the first reactant. 
Compound 4: The first reactant has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms. The second reactant has a two-carbon chain, in which C 1 is bonded to an N H 2 group. A curved arrow from the nitrogen-hydrogen single bond of the N H 3 group points toward the corresponding hydrogen atom and another curved arrow from the nitrogen atom of the N H 2 group points toward the hydrogen atom on the first reactant. 
Compound 5: The first reactant has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms. The second reactant has a two-carbon chain, in which C 1 is bonded to an N H 2 group. A curved arrow from the nitrogen-hydrogen single bond of the N H 3 group points toward the corresponding nitrogen atom and another curved arrow from the hydrogen atom of the N H 3 group points toward the nitrogen atom on the second reactant.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

37) For the following acid-base reaction, identify the correct curved arrow mechanism.

An illustration shows a chemical reaction. The reactant that has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group, reacts with N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge to yield three products. The first product has a SMILES string of CCOC(C)C. The second product is H 2 O and the third product is sodium cation, N a superscript positive.

An illustration shows set of reactants for an incomplete partial reaction.
Compound 1: The first reactant has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group. The second reactant is N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge. A curved arrow from the oxygen-hydrogen single bond of the first reactant points toward the hydrogen atom and another curved arrow from the oxygen atom of the hydroxyl group points toward the hydrogen atom of the first reactant. 
Compound 2: The first reactant has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group. The second reactant is N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge. A curved arrow from the oxygen-hydrogen single bond of the first reactant points toward the corresponding oxygen atom and another curved arrow from the hydrogen atom of the first reactant points toward the oxygen atom of the hydroxyl group
Compound 3: The first reactant has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group. The second reactant is N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge. A curved arrow from the oxygen-hydrogen single bond of the first reactant points toward the corresponding oxygen atom and another curved arrow from the oxygen atom of the hydroxyl group points toward the hydrogen atom of the first reactant. 
Compound 4: The first reactant has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group. The second reactant is N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge. A curved arrow from the oxygen-hydrogen single bond of the first reactant points toward the hydrogen atom and another curved arrow from the oxygen atom of the hydrogen atom of the first reactant points toward the oxygen atom of the hydroxyl group. 
Compound 5: The first reactant has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group. The second reactant is N a O H, in which the sodium atom carries a positive charge and the hydroxyl group carries a negative charge. A curved arrow from the oxygen-hydrogen single bond of the first reactant points toward the hydrogen atom and another curved arrow oxygen-hydrogen single bond of the first reactant points toward the oxygen atom. A third curved arrow from the oxygen atom of the hydroxyl group points toward the hydrogen atom of the first reactant.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

38) For the following acid-base reaction, identify the correct curved arrow mechanism.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC(=O)Cc1ccccc1 reacts with N a N H 2 to yield two products. The first product has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 1 carries a positive charge and C 2 is double bonded to an oxygen atom. The compound is in association with sodium cation, N a superscript positive. The second product is N H 3.

An illustration shows set of reactants for an incomplete partial reaction.
Compound 1: The first reactant has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 1 is bonded to a hydrogen atom and C 2 is double bonded to an oxygen atom. The second reactant is N a N H 3, in which the sodium atom carries a positive charge and the N H 3 group carries a negative charge. A curved arrow from the single bond between carbon-hydrogen of the first reactant points toward the hydrogen atom and another curved arrow from the N H 3 group points toward the hydrogen atom of the first reactant. 
Compound 2: The first reactant has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 1 is bonded to a hydrogen atom and C 2 is double bonded to an oxygen atom. The second reactant is N a N H 3, in which the sodium atom carries a positive charge and the N H 3 group carries a negative charge. A curved arrow from the single bond between carbon-hydrogen of the first reactant points toward the carbon atom and another curved arrow from the hydrogen atom of the first reactant points toward the N H 3 group. 
Compound 3: The first reactant has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 1 is bonded to a hydrogen atom and C 2 is double bonded to an oxygen atom. The second reactant is N a N H 3, in which the sodium atom carries a positive charge and the N H 3 group carries a negative charge. A curved arrow from the single bond between carbon-hydrogen of the first reactant points toward the hydrogen atom and another curved arrow from the hydrogen atom of the first reactant points toward the N H 3 group. 
Compound 4: The first reactant has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 1 is bonded to a hydrogen atom and C 2 is double bonded to an oxygen atom. The second reactant is N a N H 3, in which the sodium atom carries a positive charge and the N H 3 group carries a negative charge. A curved arrow from the single bond between carbon-hydrogen of the first reactant points toward the carbon atom and another curved arrow from the N H 3 group points toward the hydrogen atom of the first reactant. 
Compound 5: The first reactant has a benzene ring, in which C 1 is bonded to a three-carbon chain. In the three-carbon chain, C 1 is bonded to a hydrogen atom and C 2 is double bonded to an oxygen atom. The second reactant is N a N H 3, in which the sodium atom carries a positive charge and the N H 3 group carries a negative charge. A curved arrow from the single bond between carbon-hydrogen of the first reactant points toward the carbon atom and another curved arrow from the single bond between carbon-hydrogen of the first reactant points toward the hydrogen atom. A third curved arrow from the N H 3 group points toward the hydrogen atom of the first reactant.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

39) For the following acid-base reaction, identify the correct curved arrow mechanism.

An illustration shows a chemical reaction. The reactant that has a four-carbon chain, in which C 1 carrying a negative charge is triple bonded to C 2 and the compound is in association with the sodium cation, N a superscript positive, reacts with a molecule of water, H 2 O to yield two products. The first product has a SMILES string of CCC#C and the second product is sodium hydroxide, N a O H.

An illustration shows set of reactants for an incomplete partial reaction.
Compound 1: The first reactant has a four-carbon chain, in which C 1 carrying a lone pair of electrons and a negative charge is triple bonded to C 2, the compound is in association with the sodium cation, N a superscript positive. The second reactant has a central oxygen atom single bonded to two hydrogen atoms. A curved arrow from the hydrogen atom of the second reactant points toward the lone pair of electrons at C 1 of the first reactant. 
Compound 2: The first reactant has a four-carbon chain, in which C 1 carrying a lone pair of electrons and a negative charge is triple bonded to C 2, the compound is in association with the sodium cation, N a superscript positive. The second reactant has a central oxygen atom single bonded to two hydrogen atoms. A curved arrow from the hydrogen atom of the second reactant points toward the lone pair of electrons at C 1 of the first reactant and another curved arrow from the oxygen-hydrogen single bond of the second reactant points toward the hydrogen atom. 
Compound 3: The first reactant has a four-carbon chain, in which C 1 carrying a lone pair of electrons and a negative charge is triple bonded to C 2, the compound is in association with the sodium cation, N a superscript positive. The second reactant has a central oxygen atom single bonded to two hydrogen atoms. A curved arrow from the lone pair of electrons at C 1 of the first reactant points toward the hydrogen atom of the second reactant and another curved arrow from the oxygen-hydrogen single bond of the second reactant points toward the hydrogen atom. 
Compound 4: The first reactant has a four-carbon chain, in which C 1 carrying a lone pair of electrons and a negative charge is triple bonded to C 2, the compound is in association with the sodium cation, N a superscript positive. The second reactant has a central oxygen atom single bonded to two hydrogen atoms. A curved arrow from the hydrogen atom of the second reactant points toward the lone pair of electrons at C 1 of the first reactant and another curved arrow from the oxygen-hydrogen single bond of the second reactant points toward the oxygen atom. 
Compound 5: The first reactant has a four-carbon chain, in which C 1 carrying a lone pair of electrons and a negative charge is triple bonded to C 2, the compound is in association with the sodium cation, N a superscript positive. The second reactant has a central oxygen atom single bonded to two hydrogen atoms. A curved arrow from the lone pair of electrons at C 1 of the first reactant points toward the hydrogen atom of the second reactant and another curved arrow from the oxygen-hydrogen single bond of the second reactant points toward the oxygen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

40) The following reaction mechanism contains mistakes. Which of the following statements correctly describes how the curved arrows should be drawn?

An illustration shows a chemical reaction. The reactant that has a four-carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to an oxygen atom that is further bonded to a hydrogen atom, reacts with N a H, in which the sodium atom carries a positive charge and the hydrogen atom carries a negative charge to yield two products. A curved arrow from the hydrogen atom of the hydroxyl group on the first reactant points toward the hydrogen atom carrying a negative charge. The first product has a four-carbon chain, in which C 1 is double bonded to an oxygen atom, single bonded to an oxygen atom carrying a negative charge, and the product is in association with the sodium cation, N a superscript positive. The second product is H 2.

A) The curved arrow should start at the oxygen atom labeled (I).

B) The curved arrow should start at the hydride (IV), go to hydrogen atom (II) with a second arrow starting from the O–H bond and going to the oxygen atom (I).

C) The curved arrow should start at the O–H bond and go to hydride (IV).

D) There should be and additional arrow from the oxygen atom (I) to the sodium ion (III).

E) There should be an arrow from the oxygen atom (I) to the hydrogen atom (II).

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

41) The following reaction mechanism contains mistakes. Which of the following statements correctly describes how the first curved arrows should be drawn?

An illustration shows a chemical reaction. The reactant, C H 3 C H 2 C H 2 O H reacts with N a N H 3, in which the sodium atom carries a positive charge and the N H 3 group carries a negative charge to yield two products. A curved arrow from the hydrogen atom of the hydroxyl group on the first reactant points toward the N H 3 group. The first product is C H 3 C H 2 C H 2 O N a, in which the oxygen atom carries a negative charge and the sodium atom carries a positive charge. The second product is N H 3.

A) The curved arrow should start at sodium ion labeled (III)

B) The curved arrow should start at the hydrogen atom labeled (II)

C) The curved arrow should end at the bond between the oxygen atom (I) and the hydrogen atom (II)

D) The curved arrow should start at the nitrogen atom labeled (IV)

E) There should be an arrow from the oxygen atom (I) to the hydrogen atom (II)

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

42) The following reaction mechanism contains mistakes. Which of the following statements correctly describes how the first curved arrows should be drawn?

An illustration shows a chemical reaction. The reactant that has a four-carbon chain, in which C 1 is double bonded to an oxygen atom, single bonded to an oxygen atom carrying a negative charge, and the compound is in association with sodium cation, reacts with H B r to yield two products. A curved arrow from the oxygen atom carrying a negative charge points toward the hydrogen atom of H B r and another curved arrow from the hydrogen atom of H B r points toward the bromine atom. The first product has a SMILES string of CCCC(=O)O and the second product is sodium bromide, N a B r.

A) The first arrow (I) should start at the sodium ion.

B) The second arrow (II) should go in the opposite direction.

C) The second arrow (II) should start at the bond between the H and Br.

D) The arrow labeled II should go in the opposite direction.

E) The arrow labeled II is unnecessary.

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

43) Identify the structure produced by the following acid-base reaction mechanism.

An illustration shows an incomplete reaction. The reactant that has a benzene ring, in which C 1 is bonded to a hydroxyl group, reacts with hydroxide ion, O H superscript negative to yield a product, which is represented by a question mark. A curved arrow from C 1 of the benzene ring points toward C 2 and another curved arrow from the oxygen-hydrogen single bond of the hydroxyl group at C 1 of the benzene ring points toward C 1. A third curved arrow from the hydroxyl group of the second reactant points toward the hydrogen atom of the hydroxyl group of the first reactant.

An illustration depicts the structures of five compounds. 
Compound 1 has a benzene ring, in which C 1 is bonded to an oxygen atom carrying a negative charge. 
Compound 2 has a benzene ring, in which C 2 is double bonded to an oxygen atom. 
Compound 3 has a benzene ring, in which C 1 is bonded to an oxygen atom carrying a positive charge. 
Compound 4 has a cyclohexane ring, in which C 1 is double bonded to an oxygen atom, C 2 carries a negative charge, C 3 is double bonded to C 4, and C 5 is double bonded to C 6. 
Compound 5 has a cyclohexane ring, in which C 1 is bonded to an oxygen atom carrying a negative charge, C 2 carries a negative charge, C 3 is double bonded to C 4, and C 5 is double bonded to C 6.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

44) Identify the structure produced by the following acid-base reaction mechanism.

An illustration shows an incomplete reaction. The reactant that has a benzene ring, in which C 1 is bonded to a carbonyl group and the carbonyl carbon is bonded to a methyl group, reacts with N H 2 superscript negative to yield a product, which is represented by a question mark. A curved arrow from the carbonyl carbon points toward the double bonded oxygen atom and another curved arrow from the hydrogen atom of the methyl group points toward the carbonyl carbon. A third curved arrow from the N H 2 group points toward one of the hydrogen atoms on the methyl group.

An illustration shows the structures of five compounds. 
Compound 1 has a benzene ring, in which C 1 is bonded to a two-carbon chain. In the two-carbon chain, C 1 is double bonded to C 2 and double bonded to an oxygen atom. 
Compound 2 has a benzene ring, in which C 1 is bonded to a two-carbon chain. In the two-carbon chain, C 1 is double bonded to C 2 and single bonded to an oxygen atom carrying a negative charge.
Compound 3 has a SMILES string of CC(=O)c1ccccc1.
Compound 4 has a benzene ring, in which C 1 is bonded to a two-carbon chain. In the two-carbon chain, C 1 is double bonded to an oxygen atom and C 2 carries a negative charge. 
Compound 5 has a benzene ring, in which C 1 is bonded to a two-carbon chain. In the two-carbon chain, C 1 is bonded to a hydroxyl group and C 2 carries a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 3.2 Use curved arrow representation to show flow of electrons in acid-base reactions

45) What is the Keq for the following reaction?

An illustration shows a chemical reaction. The reactant hydronium ion, H 3 O superscript positive reacts with ethoxy ethane that has a SMILES string of CCOCC to yield two products. The first product has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to an ethyl group on either side. The second product is H 2 O.

An illustration shows five K e q values for a chemical reaction. 
Equation 1: K e q equals concentration of a compound that has a SMILES string of CCOCC times concentration of hydronium ion, H 3 O superscript positive over concentration of a compound that has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to an ethyl group on either side times concentration of H 2 O. 
Equation 2: K e q equals concentration of a compound that has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to an ethyl group on either side over concentration of a compound that has a SMILES string of CCOCC times concentration of hydronium ion, H 3 O superscript positive. 
Equation 3: K e q equals concentration of a compound that has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to an ethyl group on either side times concentration of H 2 O over concentration of a compound that has a SMILES string of CCOCC times concentration of hydronium ion, H 3 O superscript positive.
Equation 4: K e q equals concentration of a compound that has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to an ethyl group on either side over concentration of a compound that has a SMILES string of CCOCC. 
Equation 5: K e q equals concentration of a compound that has a central oxygen atom carrying a positive charge is single bonded to a hydrogen atom and single bonded to an ethyl group on either side times concentration of hydronium ion, H 3 O superscript positive over concentration of a compound that has a SMILES string of CCOCC times concentration of H 2 O.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

46) Which of the following compounds is most acidic?

An illustration depicts the structures of five compounds. 
Compound 1 has a SMILES string of CC(=O)C.
Compound 2 has a SMILES string of CC(=O)O. 
Compound 3 has a SMILES string of CC(=O)[O-]. 
Compound 4 has a two-carbon chain, in which C 1 is bonded to an N H 2 group. 
 Compound 5 has a two-carbon chain, in which C 1 is bonded to an N H group and the nitrogen atom carries a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

47) Which of the following compounds is most basic?

An illustration depicts the structures of five compounds. 
Compound 1 has a SMILES string of CC(=O)C.
Compound 2 has a SMILES string of CC(=O)O. 
Compound 3 has a SMILES string of CC(=O)[O-]. 
Compound 4 has a two-carbon chain, in which C 1 is bonded to an N H 2 group. 
 Compound 5 has a two-carbon chain, in which C 1 is bonded to an N H group and the nitrogen atom carries a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

48) Which of the following compounds is most acidic?

An illustration shows the structures of five compounds. 
Compound 1 has a SMILES string of c1ccc(cc1)O. 
Compound 2 has a SMILES string of C1CCC(CC1)O. 
Compound 3 has a SMILES string of c1ccc(cc1)CN. 
Compound 4 has a SMILES string of c1ccc(cc1)N. 
Compound 5 has a SMILES string of C1CCC(CC1)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

49) Which of the following compounds is most basic?

An illustration shows the structures of five compounds. 
Compound 1 has a SMILES string of c1ccc(cc1)O. 
Compound 2 has a SMILES string of C1CCC(CC1)O. 
Compound 3 has a SMILES string of c1ccc(cc1)CN. 
Compound 4 has a SMILES string of c1ccc(cc1)N. 
Compound 5 has a SMILES string of C1CCC(CC1)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

50) Which of the following compounds is most basic?

An illustration shows the structures of five compounds. 
Compound 1 has a benzene ring, in which C 1 carries a negative charge. 
Compound 2 has a cyclohexane ring, in which C 1 is bonded to an oxygen atom carrying a negative charge. 
Compound 3 has a five-carbon chain, in which C 1 carrying a negative charge is triple bonded to C 2 and C 4 is bonded to a methyl group. 
Compound 4 has a cyclohexane ring, in which C 1 carries a negative charge. 
Compound 5 has a cyclohexane ring, in which C 1 is replaced by a nitrogen atom carrying a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

51) For the compound shown below, rank the indicated protons in order of increasing acidity.

The structure of the compound has a SMILES string of c1ccc2c(c1)c(c[nH]2)CC(C(=O)O)N, in which the hydrogen atoms of the methylene group are labeled, Roman numeral 1; the hydrogen atoms of the N H 2 group are labeled, Roman numeral 2; and the hydrogen atom of the O H group is labeled, Roman numeral 3.

A) Least acidic: I < II < III Most acidic

B) Least acidic: II < III < I Most acidic

C) Least acidic: III < I < II Most acidic

D) Least acidic: I < III < II Most acidic

E) Least acidic: II < I < III Most acidic

Diff: 3

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

52) Histidine, an amino acid, is shown below. Rank the indicated protons in order of increasing acidity.

The structure of the compound has a cyclopentane ring, in which C 1 is replaced by a nitrogen atom that is further bonded to a hydrogen atom, C 2 is double bonded to C 3 and C 3 is replaced by a nitrogen atom, and C 4 is double bonded to C 5. C 5 is bonded to a methylene group that is further bonded to a methine group, in which the hydrogen atom is labeled, Roman numeral 2. The methine group is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms, in which one of the hydrogen atoms is labeled, Roman numeral 1. The methine group is bonded to a carbonyl group and the carbonyl carbon is bonded to a hydroxyl group, in which the hydrogen atom is labeled, Roman numeral 3.

A) Least acidic: I < II < III Most acidic

B) Least acidic: II < III < I Most acidic

C) Least acidic: III < I < II Most acidic

D) Least acidic: I < III < II Most acidic

E) Least acidic: II < I < III Most acidic

Diff: 3

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

53) For the following acid-base reaction, predict the position of the equilibrium and identify the most stable base.

An illustration shows a reversible reaction. Compound 1 that has a three-carbon chain, in which C 2 is bonded to an oxygen atom carrying a positive charge that is further bonded to a hydrogen atom and to an ethyl group, reacts with compound 2, N a O H to yield compound 3 and compound 4. The structure of compound 3 has a SMILES string of CCOC(C)C and the fourth product is H 2 O.

A) favor the right side with compound I being the most stable base

B) favor the right side with compound II being the most stable base

C) favor the right side with compound III being the most stable base

D) favor the left side with compound I being the most stable base

E) favor the left side with compound II being the most stable base

Diff: 2

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

54) For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

An illustration shows a reversible reaction. Compound 1 that has a SMILES string of CCC(=O)C reacts with compound 2, hydronium ion, H 3 O superscript positive to yield compound 3 and compound 4. The structure of compound 3 has a four-carbon chain, in which C 2 is double bonded to an oxygen atom carrying a positive charge and the oxygen atom is further bonded to a hydrogen atom. The second product is H 2 O.

A) favor the right side with compound I being the most acidic compound

B) favor the right side with compound II being the most acidic compound

C) favor the left side with compound I being the most acidic compound

D) favor the left side with compound II being the most acidic compound

E) favor the left side with compound III being the most acidic compound

Diff: 2

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

55) For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

An illustration shows a reversible reaction. Compound 1 that has a five-carbon chain, in which C 2 and C 4 are each double bonded to an oxygen atom and C 3 carries a negative charge, reacts with compound 2 that has a SMILES string of c1ccc(cc1)[NH3+] to yield compound 3 and compound 4. Compound 3 has a SMILES string of CC(=O)CC(=O)C and compound 4 has a SMILES string of c1ccc(cc1)N.

A) favor the right side with compound I being the most acidic compound

B) favor the right side with compound II being the most acidic compound

C) favor the left side with compound I being the most acidic compound

D) favor the left side with compound II being the most acidic compound

E) favor the left side with compound III being the most acidic compound

Diff: 3

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

56) For the following acid-base reaction, predict the position of the equilibrium and identify the most stable base.

An illustration shows a reversible reaction. Compound 1 that has a three-carbon chain, in which C 2 carries a negative charge and single bonded to a methyl group, the compound is in association with lithium ion, L i superscript positive, reacts with compound 2 that has a SMILES string of CC(=O)C to yield compound 3 and compound 4. Compound 3 has a SMILES string of CC(C)C. Compound 4 has a three-carbon chain, in which C 1 carries a negative charge, C 2 is double bonded to an oxygen atom, and the compound is in association with lithium ion, L i superscript positive.

A) favor the right side with compound I being the most stable base

B) favor the right side with compound II being the most stable base

C) favor the right side with compound III being the most stable base

D) favor the left side with compound I being the most stable base

E) favor the left side with compound II being the most stable base

Diff: 3

Learning Objective: 3.3 Use pKa values to compare acidity and basicity and to predict the position of equilibrium

57) Which of the following compounds is most acidic?

A) HF

B) HCl

C) HBr

D) HI

E) H2O

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

58) Which of the following compounds is most acidic?

A) CH3OH

B) HCl

C) HF

D) CH3SH

E) CH3NH2

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

59) Which of the following best explains which compound is more acidic?

HF or HBr

A) HF is more acidic due to the F atom being more electronegative than Br

B) HBr is more acidic due to the Br atom being less electronegative than F

C) HF is more acidic due to the F— anion being smaller than Br—

D) HBr is more acidic due to the Br— anion being larger than F—

E) HF is capable of participating in hydrogen bonding and therefore is a strong acid

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

60) Which of the following best explains which compound is more acidic?

CH3OH and CH3NH2

A) CH3OH is more acidic due to oxygen being more electronegative than nitrogen

B) CH3NH2 is more acidic due to nitrogen being less electronegative than oxygen

C) CH3OH is more acidic as it results in a stronger conjugate base

D) CH3NH2 is more acidic as it results in a stronger conjugate base

E) Both compounds are capable of hydrogen bonding and are of equal acidity

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

61) Which of the following best explains which proton is more acidic?

The structure of the compound has a SMILES string of c1cc(ccc1O)S, in which the hydrogen atom of the S H group is labeled, Roman numeral 1 and the hydrogen atom of the hydroxyl group is labeled, Roman numeral 2.

A) The H (I) attached to S is more acidic due to oxygen being more electronegative.

B) The H (II) attached to O is more acidic due to sulfur being more electronegative.

C) The H (I) attached to S is more acidic due to sulfur being more electronegative.

D) The H (II) attached to O is more acidic due to oxygen being more electronegative.

E) The H (I) attached to S is more acidic due to the sulfur being larger than oxygen.

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

62) Rank the indicated protons in order of increasing acidity.

The structure of the compound has a cyclohexane ring fused with a cyclopentane ring. C 1 is bonded to a hydroxyl group, in which the hydrogen atom is labeled, Roman numeral 2, C 3 is bonded to a hydrogen atom labeled, Roman numeral 1, and C 6 is replaced by a nitrogen atom that is further bonded to a hydrogen atom labeled, Roman numeral 3.

A) Least acidic: I < II < III Most acidic

B) Least acidic: II < III < I Most acidic

C) Least acidic: III < I < II Most acidic

D) Least acidic: I < III < II Most acidic

E) Least acidic: II < I < III Most acidic

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

63) Which of the following compounds is most acidic?

An illustration shows the structures of five compounds. 
Compound 1 has a SMILES string of CCC(=O)O. 
Compound 2 has a SMILES string of CCC(=O)C. 
Compound 3 has a SMILES string of CCCO. 
Compound 4 has a SMILES string of CCC(=O)[O-]. 
Compound 5 has a SMILES string of c1ccc(cc1)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

64) Consider the shown proton on each compound and identify which is most acidic.

An illustration shows the bond-line structures of five compounds.
Compound 1 has a four-carbon chain, in which C 1 is double bonded to C 2 and single bonded to a hydrogen atom, C 2 is bonded to a methyl group. 
Compound 2 has a four-carbon chain, in which C 1 is double bonded to C 2, C 2 is bonded to a methyl group, and C 3 is bonded to a hydrogen atom. 
Compound 3 has a four-carbon chain, in which C 2 is bonded to a hydrogen atom. 
Compound 4 has a four-carbon chain, in which C 2 is double bonded to an oxygen atom and C 3 is bonded to a hydrogen atom. 
Compound 5 has a four-carbon chain, in which C 2 is double bonded to an oxygen atom and C 4 is bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

65) Rank the indicated protons in decreasing order of acidity.

The structure of the compound has a two cyclohexane rings fused together. C 1 is double bonded to C 2, C 3 is bonded to a hydrogen atom labeled, Roman numeral 2, C 4 is double bonded to C 5, C 6 is bonded to a hydrogen atom labeled, Roman numeral 3, C 9 is double bonded to an oxygen atom, and C 10 is bonded to a hydrogen atom labeled, Roman numeral 1.

A) Most acidic: II > I > III Least acidic

B) Most acidic: II > III > I Least acidic

C) Most acidic: I > III > II Least acidic

D) Most acidic: I > II > III Least acidic

E) Most acidic: III > II > I Least acidic

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

66) Which compound has the most acidic proton?

An illustration shows the bond-line structures of five compounds.
Compound 1 has a four-carbon chain, in which C 2 is bonded to a hydrogen atom and a methyl group, C 3 is bonded to a methyl group. 
Compound 2 has a four-carbon chain, in which C 2 is double bonded to C 3 and single bonded to a hydrogen atom, C 3 is bonded to a methyl group. 
Compound 3 has a three-carbon chain, in which C 1 is triple bonded to C 2 and single bonded to a hydrogen atom. 
Compound 4 has a four-carbon chain, in which C 1 is bonded to a hydrogen atom, C 2 is double bonded to C 3, and C 3 is bonded to a methyl group. 
Compound 5 has a four-carbon chain, in which C 1 is bonded to a hydrogen atom, C 2 and C 3 are each bonded to a methyl group.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

67) Which of the following compounds is most acidic?

An illustration depicts the bond-line structures of five compounds. 
Compound 1 has a SMILES string of CCC(=O)O. 
Compound 2 has a SMILES string of CC(C(=O)O)F. 
Compound 3 has a SMILES string of CC(C(=O)O)Br. 
Compound 4 has a SMILES string of CC(C(=O)O)I. 
Compound 5 has a SMILES string of CC(C(=O)O)Cl.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

68) Which of the following compounds is most acidic?

An illustration depicts the bond-line structures of five compounds. 
Compound 1 has a SMILES string of C(=O)(C(F)(F)F)O.
Compound 2 has a SMILES string of C(C(=O)O)(F)F. 
Compound 3 has a SMILES string of CC(C(=O)O)F. 
Compound 4 has a SMILES string of C(C(=O)O)F. 
Compound 5 has a SMILES string of CC(C)C(=O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

69) Which of the following compounds is most acidic?

An illustration depicts the bond-line structures of five compounds. 
Compound 1 has a SMILES string of C(CCl)C(=O)O. 
Compound 2 has a SMILES string of CC(C(=O)O)F. 
Compound 3 has a SMILES string of CC(C(=O)O)Br. 
Compound 4 has a SMILES string of CC(C(=O)O)Cl. 
Compound 5 has a SMILES string of C(CF)C(=O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

70) Which of the following compounds is most acidic?

An illustration depicts the bond-line structures of five compounds. 
Compound 1 has a SMILES string of OC(=O)CC(F)Cl. 
Compound 2 has a SMILES string of C(CF)C(=O)O. 
Compound 3 has a three-carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydroxyl group, C 2 is bonded to a chlorine atom, and C 3 is bonded to a fluorine atom. 
Compound 4 has a SMILES string of CC(C(=O)O)Cl. 
Compound 5 has a three-carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydroxyl group, C 2 is bonded to a fluorine atom, and C 3 is bonded to a chlorine atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

71) Rank the following compounds in decreasing order of acidity.

An illustration shows the bond-line structures of four compounds.
Compound 1 has a SMILES string of C(CBr)C(=O)O. 
Compound 2 has a SMILES string of C(C(Br)Br)C(=O)O. 
Compound 3 has a SMILES string of CC(C(=O)O)(Br)Br. 
Compound 4 has a SMILES string of C(C(C(=O)O)Br)Br.

A) III > II > IV > I

B) II > IV > III > II

C) IV > III > II > I

D) IV > II > III > I

E) III > IV > II > I

Diff: 3

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

72) Which of the indicated protons is most acidic?

The bond-line structure of the compound has a seven-carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydroxyl group, C 2 is bonded to a nitrogen atom that is further bonded to two hydrogen atoms, C 3 is bonded to a hydroxyl group, C 4 is bonded to an S H group, C 6 is bonded to a methyl group and a hydrogen atom. The hydrogen atom at C 6, C 4, C 2, C 1, and C 3 are labeled, 1, 2, 3, 4, and 5 respectively.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

73) Which of the following best explains which proton is more acidic?

The bond-line structure of the compound has a three-carbon chain, in which C 1 is replaced by a nitrogen atom that is further bonded to a hydrogen atom labeled, 2 and single bonded to a methyl group, C 3 is bonded to a carbon atom that is further bonded to three fluorine atoms. C 3 is further bonded to an N H 2 group, in which one of the hydrogen atoms is labeled, 1.

A) The H (I) is more acidic due to having less carbons attached to the nitrogen

B) The H (II) is more acidic due to having less carbons attached to the nitrogen

C) The H (I) is more acidic due to be closer to the inductive effects of the fluorine atoms

D) The H (II) is more acidic due to be closer to the inductive effects of the fluorine atoms

E) The H (II) is more acidic due to the fluorine atoms being further away

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

74) Which of the following best explains why phenol is more acidic than ethanol.

An illustration depicts the structures of phenol and ethanol. Phenol has a SMILES string of c1ccc(cc1)O and ethanol has a SMILES string of CCO.

A) The conjugate base of phenol is resonance stabilized, resulting in a weaker conjugate base.

B) The conjugate base of phenol is resonance stabilized, resulting in a stronger conjugate base.

C) The conjugate base of phenol has a localized charge, resulting in a stronger conjugate base.

D) The conjugate base of ethanol has a localized charge.

E) The conjugate base of ethanol has a delocalized charge.

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

75) Consider the shown proton on each molecule below, and select the statement that best explains which compound is more acidic.

An illustration shows the structures of two compounds. Compound 1 has a cyclohexane ring, in which C 1 is double bonded to an oxygen atom and C 2 is bonded to a hydrogen atom. Compound 2 has a cyclohexene ring, in which C 1 is replaced by a nitrogen atom and C 3 is bonded to a hydrogen atom.

A) Compound II is more acidic; the conjugate base of compound I has the negative charge on the more electronegative oxygen atom.

B) Compound I is more acidic; the conjugate base of compound I has the negative charge on the more electronegative oxygen atom.

C) Compound II is more acidic; the conjugate base of compound II has the negative charge on the more electronegative oxygen atom.

D) Compound I is more acidic; the conjugate base of compound II has the negative charge on the more electronegative oxygen atom.

E) Both compounds are equally stable as both protons are adjacent to a double bond.

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

76) Aspartic acid, an amino acid, has the structure shown below. Which of the following best explains which proton is most acidic?

The bond-line structure of the compound has a four-carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydroxyl group, C 2 is bonded to two hydrogen atoms, C 3 is bonded to a hydrogen atom and to an N H 3 group, in which the nitrogen atom carries a positive charge, C 4 is double bonded to an oxygen atom and single bonded to a hydroxyl group. The hydrogen atoms at C 1 and C 4 are labeled, 1 and 4. The hydrogen atoms at C 2 is labeled, 5. The hydrogen atom at C 3 and the hydrogen atoms of the N H 3 group are labeled, 2 and 3 respectively.

A) Proton I is most acidic due to conjugate base stabilization by resonance and being further from the inductive effect of the positive nitrogen atom.

B) Proton II is most acidic due being attached to the carbon closest to the positive nitrogen atom.

C) Proton III is most acidic due to being attached to a positive nitrogen atom.

D) Proton IV is most acidic due to conjugate base stabilization by resonance and being closer to the inductive effect of the positive nitrogen atom.

E) Proton V is most acidic due to the possibility of conjugate base stabilization by resonance with the adjacent C=O bond.

Diff: 3

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

77) For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

An illustration shows a reversible reaction. Compound 1 that has a SMILES string of C(C(F)(F)F)O reacts with compound 2 that has a SMILES string of CC[O-] to yield compound 3 and compound 4. Compound 3 has a SMILES string of CCO and compound 4 has a SMILES string of [O-]CC(F)(F)F.

A) favor the right side with compound I being the most acidic compound

B) favor the right side with compound III being the most acidic compound

C) favor the left side with compound I being the most acidic compound

D) favor the left side with compound III being the most acidic compound

E) The reaction is at equilibrium so all the compounds are in equal concentration

Diff: 1

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

78) For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

An illustration shows a reversible reaction. Compound 1, C triple bond N, in which the carbon atom carries a negative charge reacts with compound 2 that has a central carbon atom single bonded to two hydrogen atoms and double bonded to a nitrogen atom that is further bonded to a methyl group to yield compound 3 and compound 4. The structure of compound 3 has a central carbon atom triple bonded to a nitrogen atom and single bonded to a hydrogen atom. The structure of compound 4 has a central carbon atom carrying a negative charge is single bonded to a hydrogen atom and double bonded to a nitrogen atom that is further bonded to a methyl group.

A) favor the right side with compound I being the most acidic compound

B) favor the right side with compound III being the most acidic compound

C) favor the left side with compound I being the most acidic compound

D) favor the left side with compound III being the most acidic compound

E) The reaction is at equilibrium so all the compounds are in equal concentration

Diff: 1

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

79) For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

An illustration shows a reversible reaction. Compound 1 that has a four-carbon chain, in which C 1 carries a positive charge reacts with compound 2 that has a SMILES string of CCC=C to yield compound 3 and compound 4. Compound 3 has a SMILES string of CCCC. Compound 4 has a four-carbon chain, in which C 1 is double bonded to C 2 and C 3 carries a positive charge.

A) favor the right side with compound I being the most acidic compound

B) favor the right side with compound II being the most acidic compound

C) favor the right side with compound III being the most acidic compound

D) favor the left side with compound III being the most acidic compound

E) favor the left side with compound II being the most acidic compound

Diff: 1

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

80) For the following acid-base reaction, predict the position of the equilibrium and identify the most acidic compound.

An illustration shows a reversible reaction. Compound 1 that has a SMILES string of c1ccc(cc1)S reacts with compound 2 that has a SMILES string of c1ccc(cc1)[O-] to yield compound 3 and compound 4. Compound 3 has a SMILES string of c1ccc(cc1)[S-] and compound 4 has a SMILES string of c1ccc(cc1)O.

A) favor the right side with compound I being the most acidic compound

B) favor the right side with compound III being the most acidic compound

C) favor the left side with compound I being the most acidic compound

D) favor the left side with compound III being the most acidic compound

E) the reaction is at equilibrium so all the compounds are in equal concentration

Diff: 1

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

81) For the following acid-base reaction, predict the position of the equilibrium and identify the most stable base.

An illustration shows a reversible reaction. Compound 1 that has a three-carbon chain, in which C 1 is double bonded to an oxygen atom and C 3 carries a negative charge reacts with compound 2 that has a SMILES string of CCC=O to yield compound 3 and compound 4. The structure of compound 3 has a SMILES string of CCC=O. The structure of compound 4 has a three-carbon chain, in which C 1 is double bonded to an oxygen atom and C 2 carries a negative charge.

A) favor the right side with compound I being the most stable base

B) favor the right side with compound IV being the most stable base

C) favor the left side with compound I being the most stable base

D) favor the left side with compound II being the most stable base

E) the reaction is at equilibrium so all the compounds are in equal concentration

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

82) For the following acid-base reaction, predict the position of the equilibrium and identify the most stable base.

An illustration shows a reversible reaction. Compound 1 that has a SMILES string of CCO reacts with compound 2 that has a SMILES string of [O-]CC(F)(F)F to yield compound 3 and compound 4. Compound 3 has a SMILES string of CC[O-] and compound 4 has a SMILES string of C(C(F)(F)F)O.

A) favor the right side with compound I being the most stable base

B) favor the right side with compound II being the most stable base

C) favor the left side with compound I being the most stable base

D) favor the left side with compound II being the most stable base

E) favor the left side with compound III being the most stable base

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

83) Determine if H2O is a suitable reagent to protonate each of the two compounds shown below.

An illustration shows the structures of two compounds. Compound 1 has a SMILES string of c1ccc(cc1)[O-] and compound 2 has a SMILES string of c1ccc(cc1)[S-].

A) I = yes; II = no

B) I = no; II = no

C) I = no; II = yes

D) I = yes; II = yes

E) Not possible to determine with the information provided

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

84) Determine if H2O is a suitable reagent to protonate each of the two compounds shown below.

An illustration shows the structural formulas of two compounds. Compound 1 has a central sulfur atom double bonded to two oxygen atoms, single bonded to an oxygen atom carrying a negative charge, and single bonded to a hydroxyl group. Compound 2 is amide ion, N H 2, in which the nitrogen atom carries a negative charge.

A) I = yes; II = no

B) I = no; II = no

C) I = no; II = yes

D) I = yes; II = yes

E) Not possible to determine with the information provided

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

85) Which of the following best explains if H2O is a suitable reagent to protonate the compound shown below.

The bond-line structure of the compound has a three-carbon chain, in which C 1 is bonded to a nitrogen atom carrying a negative charge that is further bonded to a hydrogen atom.

A) no, water would not protonate the compound as the resulting conjugate base would not be stabilized by resonance

B) no, water would not protonate the compound as the negative charge is more stable on the nitrogen atom

C) no, water would not protonate the compound as both water and the nitrogen in the compound have two bonds

D) yes, water would protonate the compound as the resulting conjugate base would be stabilized by resonance

E) yes, water would protonate the compound as the resulting conjugate base would have a negative on the more electronegative oxygen atom

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

86) Determine if NaOH is a suitable reagent to deprotonate each of the two compounds shown below.

An illustration shows the bond-line structures of two compounds. Compound 1 has a SMILES string of CCC#C and compound 2 has a SMILES string of CC(=O)O.

A) I = yes; II = no

B) I = no; II = no

C) I = yes; II = yes

D) I = no; II = yes

E) Not possible to determine with the information provided

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

87) Determine if NaNH2 is a suitable reagent to deprotonate each of the two compounds shown below.

An illustration shows the bond-line structures of two compounds. Compound 1 has a five-carbon chain, in which C 2 and C 4 are each double bonded to an oxygen atom, C 3 is bonded to a hydrogen atom. Compound 2 has a SMILES string of CCC#C.

A) I = yes; II = yes

B) I = no; II = no

C) I = no; II = yes

D) I = yes; II = no

E) Not possible to determine with the information provided

Diff: 2

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

88) Which of the following best explains if NaOH is a suitable reagent to deprotonate the compound shown below?

The bond-line structure of the compound has a SMILES string of CC(=C(C)C)C.

A) no, there are no protons attached to the sp2 carbons

B) no, the compound would not be soluble in NaOH

C) no, NaOH has a negative charge on an oxygen atom, whereas the compound's conjugate base would have a negative charge on the carbon atom

D) yes, NaOH is considered a strong base

E) yes, protons attached to sp2 carbons are more acidic than those attached to sp3 carbons

Diff: 3

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

89) Which of the following best explains if NaNH2 is a suitable reagent to deprotonate the compound shown below?

The bond-line structure of the compound has a SMILES string of CC(=O)CC(=O)C.

A) no, the resulting conjugate base would have a localized negative on a carbon atom where NaNH2 has a negative on the more electronegative nitrogen atom

B) no, there are no acidic protons attached to the oxygen atoms

C) no, NaNH2 produces NH3 when protonated which then will leave the reaction mixture

D) yes, the resulting conjugate base would have delocalization of charge over two oxygen atoms, whereas NaNH2 has a localized negative charge.

E) yes, as NaNH2 has only two hydrogen atoms attached to the nitrogen atom, and the compound has eight total hydrogen atoms

Diff: 3

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

90) Which of the following best explains if CH3CH2ONa is a suitable reagent to deprotonate the compound shown below?

The bond-line structure of the compound has a SMILES string of CCCNC.

A) no, CH3CH2ONa would not deprotonate the compound since nitrogen has a lone pair and will not act as an acid

B) no, CH3CH2ONa has a negative charge on an oxygen atom, whereas the compound's conjugate base would have a negative charge on a nitrogen atom

C) yes, if deprotonated the negative charge would be more stable on the nitrogen atom

D) yes, CH3CH2ONa is considered a strong base

E) yes, the nitrogen atom has a proton that can be donated to an appropriate base

Diff: 3

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

91) Which of the following best explains if H2O is a suitable reagent to protonate the compound shown below?

The structure of the compound has a benzene ring, in which C 1 is bonded to a sulfur atom carrying a negative charge and the sulfur atom is in association with the sodium ion, N a superscript positive.

A) no, water would not protonate the compound as the negative charge is more stable on the larger sulfur atom

B) no, water would not protonate the compound as the resulting conjugate base would not be stabilized by resonance

C) yes, water would protonate the compound the sodium ion rather be a counter ion to oxygen than sulfur

D) yes, water would protonate the compound as the resulting conjugate base would be stabilized by resonance

E) yes, water would protonate the compound as the resulting conjugate base would have a negative on the more electronegative oxygen atom

Diff: 3

Learning Objective: 3.6 Predict the equilibrium position of a reaction based on a comparison of the conjugate bases

92) Which of the following best describes the leveling effect?

A) the ability of a compound to dissolve in a given amount of solvent

B) the limiting of a compound's acidity or basicity by respective deprotonation or protonation by the solvent

C) the cause of weak acids or weak bases to incompletely dissociate in water

D) the reason that explains why moving down the periodic table results in compounds that are more acidic

E) the reduction of inductive effects as electronegative atoms are moved further from the acidic proton

Diff: 2

Learning Objective: 3.7 Describe the significance in understanding leveling effects

93) Which of the following solvents can be used with NaNH2?

A) CH3CH2OH

B) CH3OH

C) H2O

D) Liquid NH3

E) CH3CO2H

Diff: 2

Learning Objective: 3.7 Describe the significance in understanding leveling effects

94) Which of the following solvents cannot be used with (CH3)3COK?

A) (CH3CH2)2O

B) (CH3)3COH

C) H2O

D) Liquid NH3

E) Tetrahydrofuran (THF)

Diff: 2

Learning Objective: 3.7 Describe the significance in understanding leveling effects

95) Which of the following solvents can be used with (CH3)3CLi?

A) CH3CH2OH

B) CH3OH

C) H2O

D) Liquid NH3

E) CH3(CH2)4CH3

Diff: 2

Learning Objective: 3.7 Describe the significance in understanding leveling effects

96) As a result of the "leveling effect," the strongest acid that can exist in appreciable concentration in aqueous solution is ________.

A) H2SO4

B) HCl

C) H3O+

D) HNO3

E) H2O

Diff: 1

Learning Objective: 3.7 Describe the significance in understanding leveling effects

97) As a result of the "leveling effect," the strongest base that can exist in appreciable concentration in aqueous solution is ________.

A) (CH3)3CLi

B) NaNH2

C) H3O+

D) HO—

E) H2O

Diff: 1

Learning Objective: 3.7 Describe the significance in understanding leveling effects

98) Why is ethanol a better solvating solvent than tert-butyl alcohol?

A) ethanol is less sterically hindered and more capable of interacting with the solute

B) tert-butyl alcohol is less sterically hindered and more capable of interacting with the solute

C) ethanol is less sterically hindered and less capable of interacting with the solute

D) tert-butyl alcohol is less sterically hindered and less capable of interacting with the solute

E) tert-butyl alcohol has more carbons than ethanol making it more soluble in aqueous solutions

Diff: 1

Learning Objective: 3.8 Describe the significance in understanding solvating and steric effects

99) Identify the most sterically hindered alcohol.

A) CH3OH

B) CH3CH2OH

C) (CH3)2CHOH

D) (CH3)3COH

E) CH3CH2CH2CH2OH

Diff: 1

Learning Objective: 3.8 Describe the significance in understanding solvating and steric effects

100) What is a cation?

A) a negatively charged ion

B) a positively charged ion

C) a sodium atom

D) a hydrogen molecule

E) an atom that has gained electrons

Diff: 1

Learning Objective: 3.9 Explain what is meant by a counterion

101) What is the counterion in NaOCH2CH3?

A) Na+

B) NaO—

C) CH3CH2—

D) CH3CH2O—

E) Na—

Diff: 1

Learning Objective: 3.9 Explain what is meant by a counterion

102) What is the counterion in (CH3)3CLi?

A) CH3+

B) CH3—

C) (CH3)3C—

D) Li+

E) (CH3)3C+

Diff: 1

Learning Objective: 3.9 Explain what is meant by a counterion

103) What is a counterion in (CH3)3COK?

A) K—

B) (CH3)3CO+

C) KO—

D) (CH3)3CO—

E) K+

Diff: 1

Learning Objective: 3.9 Explain what is meant by a counterion

104) A Lewis acid is defined as ________.

A) a proton donor

B) an electron pair donor

C) a proton acceptor

D) an electron pair acceptor

E) a species that generates OH— in water

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

105) A Lewis base is defined as ________.

A) a proton donor

B) an electron pair donor

C) a proton acceptor

D) an electron pair acceptor

E) a species that generates H+ in water

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

106) CH3CH2OCH2CH3, is best classified as a ________.

A) Brønsted-Lowry acid

B) Lewis acid

C) Brønsted-Lowry base

D) Lewis base

E) Both C and D

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

107) BF3, is best classified as a ________.

A) Brønsted-Lowry acid

B) Lewis acid

C) Brønsted-Lowry base

D) Lewis base

E) Both A and D

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

108) The following compound is best classified as a ________.

The structure of the compound has a SMILES string of C1CCSC1.

A) Brønsted-Lowry acid

B) Lewis acid

C) Brønsted-Lowry base

D) Lewis base

E) Both C and D

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

109) The following compound is best classified as a ________.

The structure of the compound has a cyclohexane ring, in which C 1 carries a positive charge.

A) Brønsted-Lowry acid

B) Lewis acid

C) Brønsted-Lowry base

D) Lewis base

E) Both C and D

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

110) Which of the following compounds is not a Lewis acid?

A) BH3

B) AlCl3

C) CBr4

D) CH3CH2+

E) FeBr3

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

111) Which of the following compounds is not a Lewis acid?

A) BF3

B) FeCl3

C) CH3CH2+

D) Ph3P

E) AlBr3

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

112) For the following reaction, identify the Lewis acid.

An illustration shows a chemical reaction. Compound 1 that has a central iron atom, F e single bonded to three chlorine atoms reacts with compound 2 that has two chlorine atoms single bonded to each other to yield compound 3. The structure of compound 3 has a central iron atom single bonded to a chlorine atom carrying a negative charge on the left, a chlorine atom at the top, a chlorine atom at the bottom, and a chlorine atom carrying a positive charge on the right that is further bonded to a chlorine atom.

A) I

B) II

C) III

D) Both I and III

E) Both II and III

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

113) For the following reaction, identify the Lewis acid.

An illustration shows a chemical reaction. Compound 1 that has a central boron atom single bonded to three hydrogen atoms reacts with compound 2 that has a two-carbon chain, in which C 2 is bonded to an N H 2 group to yield compound 3. The structure of compound 3 has a central boron atom carrying a negative charge is single bonded to three hydrogen atoms and to a nitrogen atom carrying a positive charge. The nitrogen atom is further bonded to two hydrogen atoms and to an ethyl group.

A) I

B) II

C) III

D) Both I and III

E) Both II and III

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

114) For the following reaction, identify the Lewis acid.

An illustration shows a chemical reaction. Compound 1 that has a central oxygen atom carrying a positive charge is single bonded to two methyl groups and to a hydrogen atom reacts with compound 2, N a O H to yield compound 3, 4, and 5 respectively. Compound 3 has a SMILES string of COC. Compound 4 is H 2 O and compound 5 is sodium ion, N a superscript positive.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

115) For the following reaction, identify the Lewis acid.

An illustration shows a chemical reaction. Compound 1 that has a SMILES string of c1ccccc1 reacts with compound 2 that has a central nitrogen atom carrying a positive charge is double bonded to an oxygen atom on either side to yield compound 3. The structure of compound 3 has a cyclohexane ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further double bonded to an oxygen atom and single bonded to an oxygen atom carrying a negative charge, C 2 carries a positive charge, C 3 is double bonded to C 4, and C 5 is double bonded to C 6.

A) I

B) II

C) III

D) Both I and III

E) Both II and III

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

116) For the following reaction, identify the Lewis base.

An illustration shows a chemical reaction. Compound 1 that has a central boron atom single bonded to three hydrogen atoms reacts with compound 2 that has a two-carbon chain, in which C 2 is bonded to an N H 2 group to yield compound 3. The structure of compound 3 has a central boron atom carrying a negative charge is single bonded to three hydrogen atoms and to a nitrogen atom carrying a positive charge. The nitrogen atom is further bonded to two hydrogen atoms and to an ethyl group.

A) I

B) II

C) III

D) Both I and III

E) Both II and III

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

117) For the following reaction, identify the Lewis base.

An illustration shows a chemical reaction. Compound 1 that has a central iron atom, F e single bonded to three chlorine atoms reacts with compound 2 that has two chlorine atoms single bonded to each other to yield compound 3. The structure of compound 3 has a central iron atom single bonded to a chlorine atom carrying a negative charge on the left, a chlorine atom at the top, a chlorine atom at the bottom, and a chlorine atom carrying a positive charge on the right that is further bonded to a chlorine atom.

A) I

B) II

C) III

D) Both I and III

E) Both II and III

Diff: 1

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

118) For the following reaction, identify the Lewis acid and the Lewis base.

An illustration shows a chemical reaction. Compound 1 that has a SMILES string of CC(C)(C)Cl reacts with compound 2, A l C l 3 to yield compound 3. The structure of compound 3 has a three-carbon chain, in which C 2 is bonded to a methyl group and to a chlorine atom carrying a positive charge. The chlorine atom is further bonded to A l C l 3, in which the aluminum atom carries a negative charge.

A) I = Lewis base; III = Lewis acid

B) I = Lewis acid; II = Lewis base

C) I = Lewis base; II = Lewis acid

D) I = Lewis acid; III = Lewis base

E) II = Lewis base; III = Lewis acid

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

119) In a Brønsted-Lowry acid-base reaction, the conjugate acid is defined as ________.

A) a proton acceptor

B) a proton donor

C) the product resulting from loss of a proton

D) the product resulting from gaining a proton

E) the most reactive species

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

120) For the following reaction, identify the Lewis acid and the Lewis base.

An illustration shows a chemical reaction. Compound 1 that has a cyclopentane ring, in which C 1 carries a positive charge reacts with compound 2 that has a two-carbon chain, in which C 1 is bonded to an N H 2 group to yield compound 3. The structure of compound 3 has a cyclopentane ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge. The nitrogen atom is further bonded to two hydrogen atoms and to an ethyl group.

A) I = Lewis base; III = Lewis acid

B) I = Lewis acid; II = Lewis base

C) I = Lewis base; II = Lewis acid

D) I = Lewis acid; III = Lewis base

E) II = Lewis base; III = Lewis acid

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

121) Identify the expected product for the following reaction.

An illustration shows an incomplete reaction. The reactant that has a SMILES string of CSC reacts with B F 3 to yield a product, which is represented by a question mark.

An illustration shows the structures of five compounds. 
Compound 1 has a central sulfur atom carrying a negative charge is single bonded to two methyl groups and to a B F 3 group, in which the boron atom carries a positive charge. 
Compound 2 has a central sulfur atom carrying a positive charge is single bonded to two methyl groups and to a fluorine atom. 
Compound 3 has a central boron atom single bonded to two fluorine atoms and to a sulfur atom that is further bonded to a methyl group. 
Compound 4 has a central sulfur atom carrying a positive charge is single bonded to two methyl groups and to a B F 3 group, in which the boron atom carries a negative charge.
Compound 5 has a sulfur atom single bonded to a methyl group and to a methylene group. The methylene group is further bonded to a B F 3 group, in which the boron atom carries a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

122) Identify the expected product for the following reaction.

An illustration shows an incomplete reaction. The reactant that has a SMILES string of C1CCC(=O)CC1 reacts with A l C l 3 to yield a product, which is represented by a question mark.

An illustration shows the structures of five compounds. 
Compound 1 has a cyclohexane ring, in which C 1 is bonded to an oxygen atom carrying a negative and to A l C l 3, in which the aluminum atom carries a positive charge. 
Compound 2 has a cyclohexane ring, in which C 1 is double bonded to an oxygen atom carrying a positive charge that is further bonded to A l C l 3, in which the aluminum atom carries a negative charge. 
Compound 3 has a cyclohexane ring, in which C 1 is double bonded to an oxygen atom carrying a negative charge that is further bonded to A l C l 3, in which the aluminum atom carries a positive charge. 
Compound 4 has a cyclohexane ring, in which C 1 is bonded to a chlorine atom and to an oxygen atom. The oxygen atom is further bonded to A l C l 2. 
Compound 5 has a cyclohexane ring, in which C 1 is double bonded to an oxygen atom that is further bonded to a chlorine atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

123) For the following reaction identify the acid and the base and predict the products.

An illustration shows an incomplete reaction. The reactant that has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms and the reactant is in association with the chloride ion, C l superscript negative, reacts with N a C N, in which the sodium atom carries a positive charge and the cyanide group carries a negative charge to yield a product, which is represented by a question mark.

An illustration shows the structures of five compounds. 
Compound 3 has a benzene ring, in which C 1 is bonded to a nitrogen atom that is further bonded to two hydrogen atoms. 
Compound 4 is hydrogen chloride, H C l. 
Compound 5 is hydrogen cyanide, H C N. 
Compound 6 is sodium chloride, N a C l.
Compound 7 has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a negative charge that is further bonded to a hydrogen atom.

A) I = acid; II = base; products = III, V, and VI

B) I = base; II = acid; products = III and IV

C) I = acid; II = base; products = IV and VII

D) I = base; II = acid; products = III, V, and VI

E) I = acid; II = base; products = IV, V, and VI

Diff: 3

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

124) For the following reaction identify the acid and the base and predict the position of the equilibrium.

An illustration shows an incomplete reversible reaction. Compound 1 that has a five-carbon chain, in which C 2 and C 4 are each double bonded to an oxygen atom, C 3 carries a negative charge reacts with compound 2 that has a two-carbon chain, in which C 1 is bonded to an oxygen atom carrying a positive charge that is further bonded to a methyl group and a hydrogen atom. A reversible arrow points from the reactants.

A) I = acid; II = base; favor the right side

B) I = base; II = acid; favor the right side

C) I = acid; II = base; favor the left side

D) I = base; II = acid; favor the left side

E) I = acid; II = base; at equilibrium so equally favors both sides

Diff: 3

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

125) In a Brønsted-Lowry acid-base reaction, the conjugate base is defined as ________.

A) a proton acceptor

B) a proton donor

C) the product resulting from loss of a proton

D) the product resulting from gaining a proton

E) the most reactive species

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

126) Identify the conjugate base of CH3CH2OH.

An illustration depicts the structures of five compounds. The structures are as follows: 
Compound 1: C H 3 C H 2 O, in which the oxygen atom carries a negative charge.
Compound 2: C H 3 C H 2 O H 2, in which the oxygen atom carries a positive charge.
Compound 3: C H 3 C H O H, in which the carbon atom carries a positive charge.
Compound 4: a central carbon atom single bonded to a methyl group, to a hydrogen atom, and double bonded to an oxygen atom carrying a positive charge and the oxygen atom is bonded to a hydrogen atom. 
Compound 5: C H 2 C H 2 O H, in which the terminal methylene carbon carries a lone pair of electrons and a negative charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

127) Identify the conjugate acid of CH3CH2NH2.

An illustration depicts the structures of five compounds. The structures are as follows: 
Compound 1: C H 3 C H 3 N H 2, in which the nitrogen atom carries a negative charge. 
Compound 2: C H 3 C H 2 N H 3, in which the nitrogen atom carries a positive charge. 
Compound 3: C H 3 C H 2 N H 3, in which the nitrogen atom carries a negative charge. 
Compound 4: C H 2 C H 2 N H 2, in which the terminal methylene carbon carries a negative charge and a lone pair of electrons. 
Compound 5: C H 2 C H 2 N H 2, in which the terminal methylene carbon carries a positive charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.1 Define Brønsted-Lowry acid, Brønsted-Lowry base, conjugate acid, and conjugate base

128) Which of the following compounds is most acidic?

A) CH3OH

B) CH3Br

C) CH3Cl

D) CH3SH

E) CH3NH2

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

129) Which of the following compounds is least acidic?

An illustration depicts the bond-line structures of five compounds. 
Compound 1 has a SMILES string of CCC(=O)O. 
Compound 2 has a SMILES string of CC(C(=O)O)F. 
Compound 3 has a SMILES string of CC(C(=O)O)Br. 
Compound 4 has a SMILES string of CC(C(=O)O)I. 
Compound 5 has a SMILES string of CC(C(=O)O)Cl.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

130) Which of the following compounds is most acidic?

An illustration shows the bond-line structures of four compounds.
Compound 1 has a SMILES string of C(CBr)C(=O)O. 
Compound 2 has a SMILES string of C(C(Br)Br)C(=O)O. 
Compound 3 has a SMILES string of CC(C(=O)O)(Br)Br. 
Compound 4 has a SMILES string of C(C(C(=O)O)Br)Br. 
Compound 5 has a SMILES string of CC(C(=O)O)Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

131) Which of the indicated protons is least acidic?

The bond-line structure of the compound has a seven-carbon chain, in which C 1 is double bonded to an oxygen atom and single bonded to a hydroxyl group, C 2 is bonded to a nitrogen atom that is further bonded to two hydrogen atoms, C 3 is bonded to a hydroxyl group, C 4 is bonded to an S H group, C 6 is bonded to a methyl group and a hydrogen atom. The hydrogen atom at C 6, C 4, C 2, C 1, and C 3 are labeled, 1, 2, 3, 4, and 5 respectively.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.4 Compare acidity and basicity of compounds based on structural (qualitative) analysis, including conjugate base stability and a comparison of the stability of negative charges (ARIO)

132) What is an anion?

A) a negatively charged ion

B) a positively charged ion

C) a sodium atom

D) a hydrogen molecule

E) an atom that has lost electrons

Diff: 1

Learning Objective: 3.9 Explain what is meant by a counterion

133) Which of the following compounds is not a Lewis base?

A) H2O

B) NH3

C) NH2—

D) CH3CH3

E) CH3OCH3

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

134) Which of the following compounds is not a Lewis Base?

A) NaOH

B) (CH3)3COK

C) CH3CH2CH2CH2Li

D) Ph3P

E) (CH3)3C+

Diff: 2

Learning Objective: 3.10 Describe how Lewis acids and bases differ from Brønsted-Lowry acids and bases

135) Identify the conjugate acid of CH3-NH-CH3.

An illustration shows the structures of five compounds. 
Compound 1: a central nitrogen atom carrying a positive charge is single bonded to two hydrogen atoms and to two methyl groups. 
Compound 2: a central nitrogen atom single bonded to three methyl groups. 
Compound 3: a central nitrogen atom carrying a negative charge is single bonded to two methyl groups. 
Compound 4: a central nitrogen atom carrying a positive charge is single bonded to a hydrogen atom and to two methyl groups.
Compound 5: C H 3 N H 3, in which the nitrogen atom carries a positive charge.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

136) Which of the following best explains which compound is more basic?

CH3OH and CH3NH2

A) CH3OH is more basic due to oxygen being more electronegative than nitrogen

B) CH3NH2 is more basic due to nitrogen being less electronegative than oxygen

C) CH3OH is more basic as it results in a weaker conjugate acid

D) CH3NH2 is more basic as it results in a stronger conjugate acid

E) Both compounds are capable of hydrogen bonding and are of equal basicity

Diff: 1

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

137) From the two compounds below identify which is more basic along with the best explanation.

An illustration shows the structures of two compounds. 
Compound 1 has a central nitrogen atom carrying a lone pair of electrons is single bonded to two methyl groups and to a hydrogen atom. 
Compound 2 has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a lone pair of electrons and the nitrogen atom is further bonded to two hydrogen atoms.

A) I is more basic since it is only bound to one hydrogen atom

B) II is more basic due to the delocalized electrons on the nitrogen atom

C) I is more basic due to the localized electrons on the nitrogen atom

D) II is more basic due to inductive effects from the aromatic ring

E) Both compounds are capable of hydrogen bonding and are of equal basicity

Diff: 1

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

138) From the two compounds below identify which would produce the more acidic conjugate acid along with the best explanation.

An illustration shows the structures of two compounds. 
Compound 1 has a central nitrogen atom carrying a lone pair of electrons is single bonded to two methyl groups and to a hydrogen atom. 
Compound 2 has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a lone pair of electrons and the nitrogen atom is further bonded to two hydrogen atoms.

A) The conjugate acid of II is more acidic as it would have three hydrogen atoms attached.

B) The conjugate acid of I is more acidic due to protonation of the localized electrons on the nitrogen atom.

C) The conjugate acid of II is more acidic as the compound would no longer have delocalized electrons.

D) The conjugate acid of I is more acidic as compound II has resonance in the aromatic ring.

E) Once both compounds are protonated they can no longer hydrogen bond and thus are of equal acidity.

Diff: 1

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

139) Which of the indicated protons is most acidic?

The bond-line structure of the compound has a four-carbon chain. C 1 is bonded to a hydroxyl group, in which the hydrogen atom is labeled, 1 and to a hydrogen atom labeled, 2. C 2 is replaced by a nitrogen that is further bonded to a hydrogen atom labeled, 5, C 3 is bonded to a hydrogen atom, C 4 is bonded to a hydrogen atom labeled, 4 and to a nitrogen atom carrying a positive charge. The nitrogen atom is further bonded to three hydrogen atoms, in which one of the hydrogen atoms is labeled, 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

140) Which of the indicated atoms would be most basic?

The bond-line structure of the compound has a five-carbon chain, in which C 1 is double bonded to an oxygen atom labeled, 2 and single bonded to a hydroxyl group labeled, 1. C 2 is bonded to a hydroxyl group labeled, 3, C 3 is bonded to an N H 2 group labeled, 4, and C 5 is double bonded to an oxygen atom, single bonded to an N H 2 group labeled, 5.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

141) Which of the indicated protons would be most acidic?

The bond-line structure of the compound has a five-carbon chain. C 1 is double bonded to an oxygen atom and single bonded to an N H 2 group, in which the nitrogen atom carries a positive charge that is further bonded to a hydrogen atom labeled, 3. C 2 is bonded to an N H 2 group, in which the nitrogen atom carries a positive charge that is further bonded to a hydrogen atom labeled, 4. C 3 is bonded to an N H group that is further bonded to a hydrogen atom labeled, 2. C 4 is bonded to a hydroxyl group, in which the hydrogen atom is labeled, 5. C 5 is bonded to a hydrogen atom labeled, 1.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

142) For the following reaction identify the acid and the base and predict the position of the equilibrium.

An illustration shows an incomplete reversible reaction. The reactant that has a benzene ring, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further double bonded to an oxygen atom and single bonded to an oxygen atom carrying a negative charge and C 4 is bonded to an N H 2 group, reacts with another compound that has a three-carbon chain, in which C 1 is bonded to a nitrogen atom carrying a positive charge that is further bonded to three hydrogen atoms to yield a product, which is represented by a question mark.

I II

A) I = acid; II = base; favor the right side

B) I = base; II = acid; favor the right side

C) I = acid; II = base; favor the left side

D) I = base; II = acid; favor the left side

E) I = acid; II = base; at equilibrium so equally favors both sides

Diff: 3

Learning Objective: 3.5 Compare acidity and basicity of compounds based on structural (qualitative) analysis, focusing on the stability of positive charges (ARIO)

© (2021) John Wiley & Sons, Inc. All rights reserved. Instructors who are authorized users of this course are permitted to download these materials and use them in connection with the course. Except as permitted herein or by law, no part of these materials should be reproduced, stored in a retrieval system, or transmitted, in any form or by any means, electronic, mechanical, photocopying, recording or otherwise.

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Document Type:
DOCX
Chapter Number:
3
Created Date:
Aug 21, 2025
Chapter Name:
Chapter 3 Acids And Bases
Author:
David R. Klein

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