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Klein Amines Test Bank Docx Ch.22

Organic Chemistry, 4e (Klein)

Chapter 22 Amines

1) Which of the choices is a primary amine?

A) CH3CH2CH2CH2NH2

B) CH3CH2NHCH2CH(CH3)2

C) (CH3CH2)2NCH2CH(CH3)2

D) (CH3CH2)4N+ OH-

E) (CH3CH2)3N

Diff: 1

Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines

2) Which of the choices is a secondary amine?

A) CH3CH2CH2CH2NH2

B) CH3CH2NHCH2CH(CH3)2

C) (CH3CH2)2NCH2CH(CH3)2

D) (CH3CH2)4N+ OH-

E) (CH3CH2)3CNH2

Diff: 1

Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines

3) Which of the choices is a tertiary amine?

A) CH3CH2CH2CH2NH2

B) CH3CH2NHCH2CH(CH3)2

C) (CH3CH2)2NCH2CH(CH3)2

D) (CH3CH2)4N+ OH-

E) (CH3CH2)3CNH2

Diff: 1

Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines

4) Which of the choices is a quaternary ammonium salt?

A) CH3CH2CH2CH2NH3+ Cl-

B) (CH3CH2)2NH2+ Cl-

C) (CH3CH2)3NH+ Cl-

D) (CH3CH2)4N+ Cl-

E) (CH3CH2)2NCH3

Diff: 2

Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines

5) Classify each of the compounds as a primary, secondary or tertiary amine.

A) I is a primary amine, II is a secondary amine, and II is a tertiary amine

B) I is a secondary amine, II is a tertiary amine, and III is a primary amine

C) I is tertiary amine, II is a secondary amine, and III is a primary amine

D) I is a secondary amine, II is a primary amine, and III is a tertiary amine

E) I is a tertiary amine, II is a primary amine, and III is a primary amine

Diff: 1

Learning Objective: 22.1 Describe the structure of primary, secondary, and tertiary amines

6) What is the structure for 1-butanamine?

A) CH3CH2CH2CH2NH2

B) CH3CH2NHCH2CH(CH3)2

C) (CH3CH2)2NCH2CH(CH3)2

D) (CH3CH2)4N+ OH-

E) (CH3CH2)3CNH2

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

7) What is the common name for the compound shown?

The SMILES string of a molecule is CCC(C)N(CC)CC and the molecule has a four-carbon zigzag chain, in which C 1 is bonded to a nitrogen atom that is bonded to two ethyl groups and C 2 of the chain is bonded to a methyl group.

A) ethylmethylisobutylamine

B) diethylisobutylamine

C) sec-butyldiethylamine

D) 2-diethylaminobutane

E) sec-butyldimethylamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

8) What is the IUPAC name for the compound shown?

A) N,N,1-diethyl-1-ethanamine

B) N,N-diethyl-1-methyl-1-propanamine

C) 2,2-diethyl-2-butanamine

D) N,N-dimethyl-2-butanamine

E) N,N-diethyl-2-butanamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

9) What is the common name for the compound shown?

The SMILES string of a molecule is CCC(C)N(CC)CC and the molecule has a four-carbon zigzag chain, in which C 1 is bonded to a nitrogen atom that is bonded to an ethyl group and C 2 of an isopropyl group, and C 2 of the chain is bonded to a methyl group.

A) ethylisobutylisopropylamine

B) ethylisopropylbutylamine

C) sec-butylethylpropylamine

D) sec-butylethylisopropylamine

E) none of these

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

10) What is the common name for the compound shown?

The SMILES string of a molecule is c2ccc(Nc1ccccc1)cc2 and the molecule has a benzene ring, in which C 1 of the ring is bonded to an N H ring. The nitrogen atom of the N H group is bonded to a benzene ring.

A) dibenzylamine

B) diphenylamine

C) dibenzeneamine

D) phenylbenzeneamine

E) none of these

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

11) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is CCNC1CCCCC1 and the molecule has a cyclohexane ring, in which C 1 is bonded to an N H group. The nitrogen atom in the N H group is bonded to an ethyl chain.

A) N-ethylhexanamine

B) N-ethylcyclohexanamine

C) N-cyclohexylethanamine

D) N-ethylcyclopentanamine

E) N-ethylaniline

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

12) What is the common name for the compound shown?

The SMILES string of a molecule is CCNC1CCCCC1 and the molecule has a cyclohexane ring, in which C 1 is bonded to an N H group. The nitrogen atom in the N H group is bonded to an ethyl chain.

A) cyclopentylmethylamine

B) ethylhexylamine

C) cyclohexylethylamine

D) cyclohexylmethylamine

E) ethylhexylmethylamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

13) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is CN(C1CCCCC1)C2CCCC2 and the molecule has a central nitrogen atom that is bonded to a methyl group, a cyclohexane ring, and a cyclopentane ring.

A) N-cyclopentyl-N-methylcyclohexanamine

B) N-cyclohexyl-N-methylcyclohexanamine

C) N-cyclopentyl-N-methylcyclopentanamine

D) cyclohexylcyclopentylmethylamine

E) N-pentyl-N-methylhexanamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

14) What is the common name for the compound shown?

The SMILES string of a molecule is CN(C1CCCCC1)C2CCCC2 and the molecule has a central nitrogen atom that is bonded to a methyl group, a cyclohexane ring, and a cyclopentane ring.

A) N-cyclopentyl-N-methylcyclohexanamine

B) N-cyclohexyl-N-methylcyclohexanamine

C) N-cyclopentyl-N-methylcyclopentanamine

D) cyclohexylcyclopentylmethylamine

E) N-pentyl-N-methylhexanamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

15) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is CCCCNCC(C)CC and the molecule has a central N H group, in which the nitrogen atom is bonded to C 1 of a four-carbon chain and C 2 of a five-carbon chain.

A) 1-methyl-N-propyl-1-butananmine

B) 4-methyl-5-octanamine

C) 1-ethyl-N-propyl-1-pentanamine

D) N-butyl-2-pentanamine

E) N-methylpropyl-1-butanamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

16) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is CCC(CCCCN)C1CC1 and the molecule has a seven-carbon zigzag chain, in which C 1 is bonded to an amino group and C 5 is bonded to a cyclopropane ring.

A) 1-cyclopropyl-1-ethyl-6-hexamine

B) 3-cyclopropyl-7-heptamine

C) 5-cyclopropyl-1-heptanamine

D) 1-ethyl-1-cyclopropyl-6-hexamine

E) 3-cyclopropylheptamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

17) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is C[C@H]1CCC[C@@H]1N and the molecule has a cyclopentane ring, in which C 1 is wedge bonded to an amino group and C 2 is hash bonded to a methyl group.

A) (1R,2S)-2-methylcyclopentanamine

B) (1S,2R)-2-methylcyclopentanamine

C) (1S,2S)-1-methyl-3cyclopentanamine

D) (1R,2R)-1-methyl-3cyclopentanamine

E) (1S,2S)-2-methylcyclopentanamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

18) What is the structure for 3-chloro-N-ethyl-1-pentanamine?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

19) What is the structure for N-ethylbenzylamine?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

20) What is the structure for N,N-diethylaniline?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

21) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is CCC(O)CC(CC(C)N)C(C)C and the molecule has an eight-carbon zigzag chain, in which C 3 is bonded to a hydroxyl group, C 5 is bonded to C 2 of an isopropyl group, and C 7 is bonded to an amino group.

A) 7-amino-5-isopropyl-3-octanol

B) 7-amino-5-(dimethyl)-3-octanol

C) 2-amino-5-isopropyl-6-octanol

D) 2-amino-5-(dimethyl)-3-octanol

E) 1-ethyl-3-isopropyl-5-amino-1-octanol

Diff: 3

Learning Objective: 22.2 Describe two methods of naming amines

22) What is the IUPAC name for the compound shown?

A) 4-amino-2,2-ethylhexanoic acid

B) 4-amino-2-diethylhexanoic acid

C) 3-amino-5,5-ethyl-6-hexanoic acid

D) 3-amino-5,5-diethyl-6-hexanoic acid

E) 4-amino-2,2-diethylhexanoic acid

Diff: 3

Learning Objective: 22.2 Describe two methods of naming amines

23) What is the IUPAC name for the compound shown?

The SMILES string of a molecule CCC(CC(=O)CCO)CC(C)N and the molecule has an eight-carbon zigzag chain, in which C 1 is bonded to a hydroxyl group, C 3 is double bonded to an oxygen atom, C 5 is bonded to an ethyl chain, and C 7 is bonded to an amino group.

A) 7-amino-5-ethyl-hydroxyoctanone

B) 7-amino-5-ethyl-1-hydroxy-3-octanone

C) 2-amino-4-ethyl-8-hydroxy-6-octanone

D) 2-amino-4-methyl-8-hydroxy-6-octanone

E) 7-amino-1-hydroxy-5-ethyl-6-octanone

Diff: 3

Learning Objective: 22.2 Describe two methods of naming amines

24) What is the IUPAC name for the compound shown?

The SMILES string of a molecule has a central nitrogen atom that is bonded to an ethyl group, C 1 of a three-carbon zigzag chain, and C 4 of a four-carbon chain.

A) 4-amino-4-ethyloctane

B) 5-amino-5-ethyloctane

C) N-propylethyl-1-butanamine

D) N-ethylpropyl-1-butanamine

E) N-ethyl-N-propyl-1-butanamine

Diff: 3

Learning Objective: 22.2 Describe two methods of naming amines

25) What is the common name for the compound shown?

The SMILES string of a molecule has a central nitrogen atom that is bonded to an ethyl group, C 1 of a three-carbon zigzag chain, and C 4 of a four-carbon chain.

A) N-ethylbutylpropylamine

B) N-butylethylpropylamine

C) butylethylpropylamine

D) propylethylbutylamine

E) butylpropylethylamine

Diff: 2

Learning Objective: 22.2 Describe two methods of naming amines

26) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is CCC1CCC(=O)CC1N and the molecule has a cyclohexane ring, in which C 1 is double bonded to an oxygen atom, C 3 is bonded to an amino group, and C 4 is bonded to an ethyl chain.

A) 1-amino-6-ethylcyclohexan-3-one

B) 3-amino-4-ethylcyclohexanone

C) 2-amino-1-ethylcyclohexan-5-one

D) p-ethyl-m-aminocyclohexanone

E) 1-ethyl, 6-aminocyclohexan-4-one

Diff: 3

Learning Objective: 22.2 Describe two methods of naming amines

27) What is the IUPAC name for the compound shown?

The SMILES string of a molecule is C[C@@H]1CCC=C[C@@H]1N and the molecule has a cyclohexane ring, in which C 1 is double bonded to C 2, C 3 is wedge bonded to an amino group, and C 4 is wedge bonded to a methyl group.

A) (1R,6S)-6-methylcyclohex-2-enamine

B) (1S,6R)-6-methylcyclohex-2-enamine

C) (1S,6S)-6-methylcyclohex-2-enamine

D) (1R,6R)-6-methylcyclohex-2-enamine

E) (1R,6S)-6-methylcyclohex-2-amine

Diff: 3

Learning Objective: 22.2 Describe two methods of naming amines

28) Arrange the compounds shown in decreasing (highest to lowest) order of boiling point.

The chemical formula of the first molecule is C H subscript 3 C H subscript 2 C H subscript 2 C H subscript 2 N H subscript 2. The chemical formula of the second molecule is C H subscript 3 C H subscript 2 N (C H subscript 3) subscript 2. The chemical formula of the third molecule is C H subscript 3 C H subscript 2 C H subscript 2 N H C H subscript 3.

A) II > III > I

B) I > III > II

C) III > I > II

D) III > II > I

E) I > II > III

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

29) Arrange the compounds shown in decreasing (highest to lowest) order of boiling point.

The first molecule is 1-pentanol. The second molecule is hexane. The third molecule is 1-pentamine. The fourth molecule is butyl methyl ether.

A) III > I > IV > II

B) I > III > IV > II

C) I > IV > III > II

D) I > III > II > IV

E) III > I > II > IV

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

30) Which of the compounds shown is most soluble in water?

A) I

B) II

C) III

D) both I and II

E) all of these

Diff: 1

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

31) Which of the compounds shown is least soluble in water?

A) I

B) II

C) III

D) both I and III

E) none of these

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

32) Which of the compounds shown is the strongest base?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

33) Rank the compounds shown in decreasing (strongest to weakest) order of basicity.

A) I > III > II > IV

B) II > III > I > IV

C) IV > II > III > IV

D) IV > III > II > I

E) III > II > I > IV

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

34) Arrange the compounds shown in decreasing (strongest to weakest) order of basicity.

The chemical formula of the first molecule is C H 3 C H 2 N H 2. The chemical formula of the second molecule is (C H 3 C H 2) 3 N. The chemical formula of the third molecule is N H 3. The chemical formula of the fourth molecule is (C H 3 C H 2) 2 N H.

A) I > III > II > IV

B) II > III > I > IV

C) IV > II > I > III

D) IV > III > II > I

E) II > I > IV > III

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

35) Arrange the compounds shown in decreasing (strongest to weakest) order of basicity.

The first molecule is p-methyl aniline. The second molecule is aniline. The third molecule is p-nitro aniline. The fourth molecule is p-methoxy aniline.

A) I > III > II > IV

B) II > III > I > IV

C) IV > III > II > I

D) IV > I > II > III

E) II > I > IV > III

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

36) Arrange the compounds shown in decreasing (strongest to weakest) order of basicity.

A) I > III > II > IV

B) II > III > I > IV

C) IV > III > II > I

D) IV > I > II > III

E) II > IV > I > III

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

37) Which of the choices is the weakest base?

A) 4-chloroaniline

B) 4-nitroaniline

C) 4-aminobenzonitrile

D) aniline

E) 4-aminoanisole

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

38) Which of the choices is the strongest base?

A) 4-chloroaniline

B) 4-nitroaniline

C) 4-aminobenzonitrile

D) aniline

E) 4-aminoanisole

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

39) Arrange the compounds shown in increasing (weakest to strongest) order of basicity.

A) IV < II < I < III

B) III < II < IV < I

C) II < I < III < IV

D) II < III < I < IV

E) none of the above

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

40) Which one of the compounds shown, if either, is a stronger base and why?

A) I is a stronger base because the nonbonding electrons on N are not involved in resonance in the aromatic ring.

B) I is a stronger base because the nonbonding electrons on N are involved in resonance in the aromatic ring.

C) II is a stronger base because the nonbinding electrons on N are involved in resonance on the aromatic ring.

D) II is a stronger base because the nonbonding electrons on N are not involved in resonance on the aromatic ring.

E) I and II are equivalent bases because both have nonbonding electrons that are involved resonance.

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

41) Pyridoxamine, aka vitamin B6, has the structure shown. Which nitrogen is more basic and why?

A) N2 is more basic because it is sp hybridized.

B) N2 is more basic because it is sp3 hybridized.

C) N1 is more basic because it is sp hybridized and more electronegative than N2.

D) N1 is more basic as it is sp3 hybridized and is less electronegative than N2.

E) N1 is more basic as it is sp2 hybridized and more electronegative than N2.

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

42) Nicotine, present in tobacco, has the structure shown. Which nitrogen is more basic and why?

A) N2 is more basic as it is sp3 hybridized and less electronegative than N1.

B) N2 is more basic as it is sp2 hybridized and less electronegative than N1.

C) N2 is more basic as it is sp3 hybridized and more electronegative than N1.

D) N1 is more basic as it is sp3 hybridized and more electronegative than N2.

E) N1 is more basic as it is sp hybridized and more electronegative than N2.

Diff: 3

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

43) Chloroquine is used as an antimalarial drug. Rank the three nitrogen atoms in decreasing (strongest to weakest) order of basicity.

A) III > I > II

B) I > III > II

C) II > I > III

D) I > II > III

E) III > II > I

Diff: 2

Learning Objective: 22.3 Discuss the properties of amines, including atomic structure, solubility, boiling point, odor, acidity, and basicity, and describe the process of solvent extraction

44) What is the predicted product of the reaction shown?

A chemical reaction shows a molecule with SMILES string of CCCCCC#N and the molecule has a five-carbon zigzag chain, in which C 1 is cyanide group. This molecule can react with molecular hydrogen in the presence of nickel.

An illustration depicts bond-line structures of two possible products. The SMILES string of the first possible product is CCCCCN and the molecule has a five-carbon zigzag chain, in which C 1 is bonded to an amino group. The SMILES string of the second possible product is CCCCCCN and the molecule has a five-carbon zigzag chain, in which C 1 is bonded to an amino group.

The SMILES string of the fifth possible product is CCCCCC=N and the molecule has a six-carbon zigzag chain, in which C 1 is double bonded to a nitrogen atom that is further bonded to a hydrogen atom.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

45) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

46) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant has a SMILES string of C/C=C/CC(C)[NO2] and the reactant has a six-carbon zigzag chain, in which C 2 is double bonded to C 3 and C 5 is bonded to a nitro group. The product formed has a SMILES string of C/C=C/CC(C)N and the product has a six-carbon zigzag chain, in which C 2 is double bonded to C 3 and C 5 is bonded to an amino group.

A) H2 and Ni

B) 1. LiAlH4

2. H2O

C) Fe and HCl

D) Zn and HCl

E) all of these

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

47) What is the predicted product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string of C=Cc1ccccc1[NO2] and the molecule has a benzene ring, in which C 1 of the ring is bonded to a nitro group and C 2 of the ring is bonded to C 1 of a two-carbon chain. In the two-carbon chain, C 1 is double bonded to C 2. The reactant reacts with molecular hydrogen in the presence of nickel.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

48) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

49) What is the predicted product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string of NC(=O)c1ccccc1 and the molecule has a benzene ring, in which C 1 of the ring is bonded to a carbon atom that is double bonded to an oxygen atom and further bonded to an amino group. The reactant reacts with lithium aluminum hydride in the presence of water.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

50) What is the predicted product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string of C1CCNCC1 and the molecule has a cyclohexane ring, in which C 1 of the ring is replaced by an N H group and C 2 is double bonded to an oxygen atom. The reactant reacts with lithium aluminum hydride in the presence of water.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

51) What reagents are necessary to carry out the conversion shown?

In a chemical reaction, the reactant has a SMILES string of CCCCC(N)=O and the reactant has a five-carbon zigzag chain, in which C 1 is double bonded to oxygen atom and C 1 is further bonded to an amino group. The product formed has a SMILES string of CCCCCN and the product has a five-carbon zigzag chain, in which C 1 is bonded to an amino group.

A) H2 and Ni

B) 1. LiAlH4; 2. H2O

C) Fe and HCl

D) Zn and HCl

E) Fe and H2O

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

52) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

53) What reagents are needed to convert (S)-3-methyl-3-phenylpentanoic acid to (S)-3-methyl-3-phenylpentanamine?

A) 1. NaCN; 2. LiAlH4; 2. H2O

B) 1. HNO3/H2SO4; 2. H2/Pt

C) 1. NaN3; 2. LiAlH4; 3. H2O

D) 1. SOCl2/pyridine; 2. NH3; 3. LiAlH4; 4.H2O

E) 1. SOCl2/pyridine; 2. LiAlH4; 3.H2O

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

54) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant has a SMILES string of BrCc1ccccc1 and the reactant has a benzene ring, in which C 1 is bonded to a methylene group that is bonded to a bromine atom. The product formed has a SMILES string of NCCc1ccccc1 and the product has a benzene ring, in which C 1 is bonded to C 2 of an ethyl group. In the ethyl group, C 1 is bonded to an amino group.

A) 1. NaCN; 2. LiAlH4; 2. H2O

B) 1. HNO3/H2SO4; 2. H2/Pt

C) 1. NaN3; 2. LiAlH4; 3. H2O

D) 1. SOCl2/pyridine; 2. NH3; 3. LiAlH4; 4.H2O

E) 1. SOCl2/pyridine; 2. LiAlH4; 3.H2O

Diff: 2

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

55) What reagents are needed to carry out the conversion shown?

A) 1. NaCN; 2. LiAlH4; 2. H2O

B) 1. HNO3/H2SO4; 2. H2/Pt

C) 1. NaN3; 2. LiAlH4; 3. H2O

D) 1. SOCl2; 2. excess NH3; 3. excess LiAlH4; 4.H2O

E) 1. SOCl2/pyridine; 2. LiAlH4; 3.H2O

Diff: 3

Learning Objective: 22.4 Identify the reagents necessary to prepare amines from alkyl halides or carboxylic acids

56) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

57) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

58) What is the predicted product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string of CCC(CC)CCBr and the molecule has a five-carbon zigzag chain, in which C 1 is bonded to a bromine atom and C 3 is bonded to an ethyl group. The reactant reacts with three reagents. The first reagent is sodium azide, N a N subscript 3. The second reagent is lithium aluminum hydride, L i A l H subscript 4. The third reagent is water.

An illustration depicts bond-line structures of three possible products. The SMILES string of the first possible product is CCC(CC)CCNN. The SMILES string of the second possible product is CCC(CC)CCN. The SMILES string of the third possible product is CCC(CC)C/C=N/N.

An illustration depicts bond-line structures of two possible products. The SMILES string of the fourth possible product is CCC(CC)CCN=N. The SMILES string of the fifth possible product is CCC(CC)CCC(N)=O.

A) I

B) II

C) III

D) IV

E) III and IV

Diff: 2

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

59) What is the predicted product of the reaction shown?

In a chemical reaction, bromo cyclopentane ring reacts with sodium azide and molecular hydrogen in the presence of palladium to form an unknown product.

An illustration depicts structures of five possible products. The SMILES string of the first possible product is [N3]C1CCCC1. The SMILES string of the second possible product is [Pd]C1CCCC1. The SMILES string of the third possible product is C1CCCC1. The SMILES string of the fourth possible product is CC1CCCN1. The SMILES string of the fifth possible product is NC1CCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

60) What is the predicted product of the reaction shown?

In a chemical reaction, the reactant with SMILES string CC(C)C[N3] reacts with lithium aluminum hydride and water to form an unknown product.

An illustration depicts bond-line structures of five possible products. The SMILES string of the first possible product is CC(C)N[N3]. The SMILES string of the second possible product is CC(N)CN. The SMILES string of the third possible product is CC([Li])CN. The SMILES string of the fourth possible product is CC(C)C[Li]. The SMILES string of the fifth possible product is CC(C)CN.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

61) What is the predicted product of the reaction sequence shown?

In a chemical reaction, the reactant with SMILES string CC1=CCCCC1 undergoes a three-step reaction to form an unknown product. The first reagent is m C P B A. The second reagent is sodium azide. The third reagent is lithium aluminum hydride and water.

The first pair of possible product has SMILES string C[C@]1(O)CCCC[C@@H]1N and an enantiomer. The second pair of possible product has SMILES string C[C@]1([N3])CCCC[C@@H]1O and an enantiomer. The third pair of possible product has SMILES string C[C@@]1(N)CCCC[C@H]1O and an enantiomer.

The fourth pair of possible product has SMILES string C[C@]1(O)CCCC[C@H]1N and an enantiomer. The fifth pair of possible product has SMILES string C[C@]1(O)CCCC[C@H]1[N3] and an enantiomer.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

62) Which of these alkyl halides cannot be used to prepare amines using Gabriel synthesis?

A) 1-bromopentane

B) 1-bromo-3-methylbutane

C) 2-bromo-3-methylpentane

D) 1-bromo-2,3-dimethylbutane

E) 2-bromo-2,3-dimethylbutane

Diff: 2

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

63) What is(are) the predicted product(s) of the reaction shown?

An illustration shows an incomplete reaction and possible products labeled 1 through 5.
In the chemical reaction, the reactant with SMILES string of c1ccc2c(c1)C(=O)NC2=O reacts with four reagents to form the unknown product(s). The first reagent is potassium hydroxide. The second reagent is butyl bromide. The third reagent is hydronium ion. The fourth reagent is sodium hydroxide.

Labeled 1: The pair of two possible products are formed. First product has SMILES string O=C(O)c1ccccc1C(=O)O and second product is amino butane.

Labeled 2: The pair of two possible products are formed. First product has SMILES string NC(=O)c1ccccc1C(=O)O and second product is amino propane.

Labeled 3: The pair of two possible products are formed. First product has SMILES string NC(=O)c1ccccc1C(=O)O and second product is amino butane.

Labeled 4: The fourth possible product has SMILES string of CCCCn2c(=O)c1ccccc1c2=O.

Labeled 5: The pair of two possible products are formed. First product has SMILES string O=c1[nH][nH]c(=O)c2ccccc12 and second product is amino butane.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

64) Provide a stepwise synthesis of 3-amino-2-methylpentane using the Gabriel synthesis.

A) 1. KOH; 2. The bond-line structure of a molecule has a SMILES string of CCC(Br)CC and it has a five-carbon zigzag chain, in which C 3 is bonded to a bromine atom. ; 3. H3O+; 4. NaOH

B) 1. KOH; 2. The bond-line structure of a molecule has a SMILES string of CCC(Br)C(C)C and it has a five-carbon zigzag chain, in which C 2 is bonded to a methyl group and C 3 is bonded to a bromine atom. ; 3. H3O+; 4. NaOH

C) 1. LiAlH4; 2. The bond-line structure of a molecule has a SMILES string of CCC(Br)C(C)C and it has a five-carbon zigzag chain, in which C 2 is bonded to a methyl group and C 3 is bonded to a bromine atom. ; 3. H3O+; 4. NaOH

D) 1. LiAlH4; 2. The bond-line structure of a molecule has a SMILES string of CCC(C)CBr and it has a four-carbon zigzag chain, in which C 1 is bonded to a bromine atom and C 2 is bonded to a methyl group. ; 3. H3O+; 4. NaOH

E) 1. KOH; 2. The bond-line structure of a molecule has a SMILES string of CCC(C)CBr and it has a four-carbon zigzag chain, in which C 1 is bonded to a bromine atom and C 2 is bonded to a methyl group. ; 3. H3O+; 4. NaOH

Diff: 3

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

65) Provide a stepwise synthesis of 1-cyclopentylethanamine using the Gabriel synthesis.

A) 1. KOH; 2. The SMILES string of a molecule CC(Br)C1CCCC1 and the molecule has a cyclopentane ring, in which C 1 is bonded to an ethyl chain and C 1 of ethyl chain is bonded to a bromine atom. ; 3. H3O+

B) 1. KOH; 2. The SMILES string of a molecule BrC1CCCC1 and the molecule has a cyclopentane ring, in which C 1 is bonded to a bromine atom. ; 3. H3O+

C) 1. LiAlH4; 2. The SMILES string of a molecule BrC1CCCC1 and the molecule has a cyclopentane ring, in which C 1 is bonded to a bromine atom. ; 3. H3O+

D) 1. LiAlH4; 2. The SMILES string of a molecule CC(Br)C1CCCC1 and the molecule has a cyclopentane ring, in which C 1 is bonded to an ethyl chain and C 1 of ethyl chain is bonded to a bromine atom. ; 3. H3O+

E) 1. KOH; 2. The SMILES string of a molecule BrC(Br)C1CCCC1 and the molecule has a cyclopentane ring, in which C 1 is bonded to a methylene group that is bonded to two bromine atoms. ; 3. H3O+

Diff: 3

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

66) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

67) The ________ reaction is used to prepare primary amines by using potassium phthalimide. This reaction proceeds by a ________ mechanism.

A) Azide; E1

B) Gabriel; SN2

C) Gabriel; SN1

D) Hofmann; E2

E) Hofmann; SN1

Diff: 1

Learning Objective: 22.5 Identify three methods for preparing an amine via a substitution reaction

68) What is the predicted product of the reaction shown?

An illustration depicts bond-line structures of three possible products. The SMILES string of the first possible product is CCC/C(C)=N/CC. The SMILES string of the second possible product is CCCC(C)NCC. The SMILES string of the third possible product is CCCC(C)(O)NCC.

An illustration depicts bond-line structures of two possible products. The SMILES string of the fourth possible product is CCCC(C)(NCC)NCC. The SMILES string of the fifth possible product is CCCC(=O)NCC.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

69) What is(are) the predicted product(s) of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

70) What is the predicted product of the reaction shown?

An illustration depicts structures of three possible products. The SMILES string of the first possible product is C2CC/C(=[N]/C1CCCC1)CC2. The SMILES string of the second possible product is OC2(NC1CCCC1)CCCCC2. The SMILES string of the third possible product is O=C1CCCCN1C2CCCC2.

$An illustration depicts structures of two possible products. The SMILES string of the fourth possible product is C2CCC(NC1CCCC1)CC2. The SMILES string of the fifth possible product is OC2(/N=C\1CCCC1)CCCCC2.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

71) What is the predicted product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

72) Provide the reagents necessary to carry out the following conversion.

In a chemical reaction, the reactant benzene undergoes a reaction to form a product with SMILES string CCNC(C)c1ccccc1. The product has a benzene ring, in which C 1 is bonded to C 1 of an ethyl chain. In the ethyl chain, C 1 is bonded to an N H group that is further bonded to an ethyl chain.

A) 1. NaNO2; 2. HCl; 3. NH3

B) 1. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; CH3CH2NH2, H2SO4, NaBH3CN

C) 1. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; CH3CH2NH2, H2SO4

D) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. NaBH3CN

E) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; CH3CH2CH2NH2, H2SO4, NaBH3CN

Diff: 3

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

73) What are the structures of the products in each step of the reaction sequence shown?

A) A is I, B is II, and C is III

B) A is II, B is III, and C is IV

C) A is II, B is I, and C is III

D) A is II, B is IV, and C is III

E) A is IV, B is I, and C is III

Diff: 3

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

74) What are the structures of the products in each step of the reaction sequence shown?

A) A is I, B is II, and C is III

B) A is II, B is III, and C is IV

C) A is II, B is I, and C is III

D) A is II, B is IV, and C is III

E) A is IV, B is I, and C is III

Diff: 3

Learning Objective: 22.6 Explain the process of reductive amination, including possible starting materials and reagents

75) What is the predicted product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: 22.8 Describe the reaction of amines with acyl halides, and explain why acylation of the amino group is a useful technique

76) What reagents are needed necessary to carry out the conversion shown?

In a chemical reaction, the reactant benzene undergoes a reaction to form a product with SMILES string CCC(=O)Nc1ccc(Cl)c(Cl)c1. The product has a benzene ring, in which C 1 and C 2 are each bonded to a chlorine atom and C 4 is bonded to an N H group. The nitrogen atom of N H group is further bonded to C 1 of a three-carbon chain, in which C 1 is double bonded to an oxygen atom.

A) 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. Fe/HCl; 4. The formula of propionyl chloride, C H subscript 3 C H subscript 2 C double bonded O C l and aluminum chloride, A l C l 3.

B) 1. KOH; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. The formula of propionyl chloride, C H subscript 3 C H subscript 2 C double bonded O C l and aluminum chloride, A l C l 3.

C) 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. The formula of propionyl chloride, C H subscript 3 C H subscript 2 C double bonded O C l and aluminum chloride, A l C l 3.

D) 1. Cl2/FeCl3; 2. NH3/H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. The formula of propionyl chloride, C H subscript 3 C H subscript 2 C double bonded O C l and aluminum chloride, A l C l 3.

E) 1. HCl/FeCl3; 2. H2SO4; 3. Cl2/FeCl3; 4. Fe/HCl; 5. The formula of propionyl chloride, C H subscript 3 C H subscript 2 C double bonded O C l and aluminum chloride, A l C l 3.

Diff: 3

Learning Objective: 22.8 Describe the reaction of amines with acyl halides, and explain why acylation of the amino group is a useful technique

77) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant nitro benzene undergoes a reaction to form a product with SMILES string Nc1ccc(Br)cc1. The product has a benzene ring, in which C 1 is bonded to an amino group and C 4 is bonded to a bromine atom.

A) 1. HBF4; 2. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 3. Br2/FeBr3; 4. Na2CO3

B) 1. Fe/HCl; 2. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 3. Br2/FeBr3; 4. H3O+; 5. dil. Na2CO3

C) 1. HBr; 2. Br2/FeBr3; 3. H3O+; 4. dil. Na2CO3

D) 1. Br2, hv; 2. H3O+; 3. dil. Na2CO3

E) 1. NaNO2/HCl; 2. Br2/FeBr3; 3. H3O+

Diff: 3

Learning Objective: 22.8 Describe the reaction of amines with acyl halides, and explain why acylation of the amino group is a useful technique

78) What is the predicted major product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string CC(C)CC(C)N and the reactant has a five-carbon zigzag chain, in which C 2 is bonded to an amino group and C 4 is bonded to a methyl group. The reactant undergoes in the presence of two sets of reagent to form an unknown product. The first reagent is excess methyl iodide. The second reagent is silver oxide, A g 2 O, water and heat.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.9 Predict the products of a Hofmann elimination

79) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) I and III

Diff: 3

Learning Objective: 22.9 Predict the products of a Hofmann elimination

80) What is the predicted major product of the reaction shown?

$In a chemical reaction, the reactant has a SMILES string CC1(N)CCCCC1 and the reactant has a cyclohexane ring, in which C 1 is bonded to a methyl group and an amino group. The reactant undergoes in the presence of two sets of reagent to form an unknown product. The first reagent is excess methyl iodide. The second reagent is silver oxide, A g 2 O, water and heat.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.9 Predict the products of a Hofmann elimination

81) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant has the SMILES string CC(=O)c1ccccc1 that reacts with an unknown reagent A to form a new product. The product formed has a SMILES string CC(N)c1ccccc1. This product further reacts with an unknown reagent B to form a new product. The product formed has a SMILES string C=Cc1ccccc1.

In a chemical reaction, an unknown reagent C reacts and forms a product. The product formed has SMILES string c2ccc(C1CO1)cc2. This product further reacts with an unknown reagent D to form the product with SMILES string NCC(O)c1ccccc1.

A) 1. KOH; 2. H2/Pt; 3. excess CH3I; 4. Ag2O, H2O; 5. mCPBA

B) 1. NH3; 2. H2/Pt; 3. excess CH3I; 4. Ag2O, H2O; 5. mCPBA

C) 1. NH3; 2. H2/Pt; 3. Ag2O, H2O; 4. mCPBA; 5; NH3

D) 1. NaOH; 2. excess CH3I; 3. mCPBA; 4; NH3

E) 1. NH3; 2. H2/Pt; 3. excess CH3I; 4. Ag2O, H2O; 5. mCPBA; 6; NH3

Diff: 3

Learning Objective: 22.9 Predict the products of a Hofmann elimination

82) What reagent(s) is(are) needed to carry out the conversion shown?

In a chemical reaction, the reactant has a SMILES string Nc1ccc([NO2])cc1 and the reactant has a benzene ring, in which C 1 is bonded to a nitro group and C 4 is bonded to an amino group. The reactant undergoes a reaction to form a product. The product formed has SMILES string Clc1ccc([NO2])cc1.

A) 1. NaNO2/HCl; <5°C; 2. CuCl

B) CuCl

C) 1. KOH; 2. CuCl; 3. H2O

D) 1. H3PO2; 2. Cl2, hv

E) 1. NaNO2/HCl; 2. Cl2

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

83) What is reagent A, which is needed to carry out the conversion shown?

A) H3PO2

B) HCN

C) H2O

D) CH3OH, heat

E) NaOCH3

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

84) What is reagent A, which is needed to carry out the conversion shown?

A) Br2/FeBr3

B) CuBr

C) NaOH

D) H3PO2

E) H3PO4

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

85) Which one of the following is the best synthesis for 3,5-dibromotoluene?

A) toluene, Br2/FeBr3 excess

B) 1. p-toluidine, Br2/ FeBr3;

2. NaNO2/HCl, < 5°C

3. H3PO2

C) 1. Toluene, HNO3/H2SO4

2. NH3

3. NaNO2/HCl, < 5°C

4. CuBr

D) m-dibromobenzene, CH3Cl/AlCl3

E) 1. m-bromotoluene, HNO3, H2SO4

2. Fe/HCl

3. NaNO2/HCl, < 5°C

4. CuBr

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

86) What reagents are necessary to carry out the conversion shown?

1. CH3CH2Cl/AlCl3

2. HNO3/H2SO4

3. Cl2/FeCl3

4. Fe/HCl

5. NaNO2/HCl/ < 5°C

6. HBF4

7. Na2Cr2O7/H2SO4/H2O

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

87) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant benzene undergoes a reaction to form a product with SMILES string CCC(=O)c1cccc(OC)c1. The product has a benzene ring, in which C 1 is bonded to an oxygen atom that is further bonded to a methyl group and C 3 is bonded to C 1 of a three-carbon chain. In the three-carbon chain, C 1 is double bonded to an oxygen atom.

A) 1. The formula of propionyl chloride, C H 3 C H C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. CH3CH2OH/heat

B) 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; H2SO4

C) 1. The formula of propionyl chloride, C H 3 C H C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. H2SO4; 2. Cl2/hv3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

88) Provide the reagents necessary to carry out the following conversion.

In a chemical reaction, the reactant benzene undergoes a reaction to form a product with SMILES string CCOc1cccc(Br)c1. The product has a benzene ring, in which C 1 is bonded to an oxygen atom that is further bonded to an ethyl group and C 3 is bonded to a bromine atom.

A) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. CH3CH2OH/heat

B) 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; H2SO4

C) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. H2SO4; 2. Cl2/hv3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

89) Provide the reagents necessary to carry out the following conversion.

In a chemical reaction, the reactant benzene undergoes a reaction to form a product with SMILES string Oc1ccc([NO2])cc1. The product has a benzene ring, in which C 1 is bonded to a hydroxyl group and C 4 is bonded to a nitro group.

A) 1. HNO3/H2SO4; 2. Fe/HCl; 3. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 4. HNO3/H2SO4; 5. H3O+; 6. NaNO2/HCl/< 5°C

B) 1. HNO3/H2SO4; 2. Cl2/FeCl3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; H2SO4

C) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. HNO3/H2SO4; 2. Fe/HCl; 3. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 4. HNO3/H2SO4; 5. H3O+; 6. NaNO2/HCl/< 5°C; 5. H2O/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

90) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant benzene undergoes a reaction to form a product with SMILES string CC(C)c1cccc(C(C)C)c1O. The product has a benzene ring, in which C 1 is bonded to a hydroxyl group and C 2 and C 6 are each bonded to C 2 of propyl group.

A) 1. HNO3/H2SO4; 2. Sn/HCl; 3. NaNO2/HCl/< 5°C; 4. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3; 6. H3O+/heat

B) 1. HNO3/H2SO4; 2. NaNO2/HCl/< 5°C; 3. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3

C) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. HNO3/H2SO4; 2. Fe/HCl; 3. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 4. HNO3/H2SO4; 5. H3O+; 6. NaNO2/HCl/< 5°C; 5. H2O/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

91) What reagents are needed to carry out the conversion shown?

A) 1. HNO3/H2SO4; 2. Sn/HCl; 3. NaNO2/HCl/< 5°C; 4. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3; 6. H3O+/heat

B) 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Na2Cr2O7/H2SO4/H2O; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 6. CuCN

C) 1. Na2Cr2O7/H2SO4/H2O; 2. CH3CH2Cl/AlCl3; 3. HNO3/H2SO4; 5. Fe/HCl; 6. NaNO2/HCl/< 5°C; 6. CuCN

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. HNO3/H2SO4; 2. Fe/HCl; 3. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 4. HNO3/H2SO4; 5. H3O+; 6. NaNO2/HCl/< 5°C; 5. H2O/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

92) What reagents are needed to carry out the conversion shown?

In a chemical reaction, the reactant has SMILES string Cc1cccc(N)c1 and the reactant forms a product with SMILES string O=C(O)c1c(Br)cc(Br)cc1Br.

A) 1. HNO3/H2SO4; 2. Sn/HCl; 3. NaNO2/HCl/< 5°C; 4. H2O/heat; 6. fuming H2SO4; 5. excess (CH3)2CHCl/AlCl3; 6. H3O+/heat

B) 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Na2Cr2O7/H2SO4/H2O; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 6. CuCN

C) 1. HBr/heat; 2. NaNO2/HCl/< 5°C; 3. H2SO4; 4. KMnO4/NaOH/H2O; H3O+

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. Br2/FeBr3 excess; 2. NaNO2/HCl/< 5°C; 3. H3PO2; 4. KMnO4/NaOH/H2O; H3O+

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

93) What is an appropriate stepwise synthesis to carry out the conversion shown?

In a chemical reaction, benzene reacts undergoes a reaction to form a product with SMILES string CCCc1cccc(CN)c1. The product has a benzene ring, in which C 1 is bonded to a methylene group that is further bonded to an amino group and C 3 is bonded to C 1 of a three-carbon chain.

In a chemical reaction, the reactant with SMILES string CCC(=O)c1cccc([N+]#N[Cl-])c1 reacts with copper cyanide to form a new product. The product has SMILES string CCC(=O)c1cccc(C#N)c1.

A) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CuCN; 6. Zn(Hg)/HCl; 7. LiAlH4; 8. H3O+

B) 1. CH3CH2Cl/AlCl3; 2. HNO3/H2SO4; 3. Na2Cr2O7/H2SO4/H2O; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 6. CuCN

C) 1. HBr/heat; 2. NaNO2/HCl/< 5°C; 3. H2SO4; 4. KMnO4/NaOH/H2O; H3O+

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. The formula of propionyl chloride, C H 3 C H 2 C double bonded O C l and aluminum chloride, A l C l 3. ; 2. Br2/AlBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CuCN; 6. Zn(Hg)/HCl; 7. LiAlH4; 8. H3O+

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

94) What is an appropriate stepwise synthesis to carry out the conversion shown?

In a chemical reaction, benzene reacts undergoes a reaction to form a product with SMILES string Brc1cccc(Br)c1I. The product has a benzene ring, in which C 1 is bonded to an iodine atom and C 2 and C 6 are each bonded to a bromine atom.

In a chemical reaction, molecular bromine and ferric bromide reacts to form a product with SMILES string CC(=O)Nc1c(Br)cc([HSO3])cc1Br. This product further reacts excess hydronium cation and heat to form another product with SMILES string Nc1c(Br)cccc1Br.

B) 1. HNO3/H2SO4; 2. Sn/HCl; 3. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 4. fuming H2SO4; 5. Br2/FeBr3; 4. excess H3O+/heat; 5. NaNO2/HCl/< 5°C; 6. CuI

C) 1. HBr/heat; 2. NaNO2/HCl/< 5°C; 3. H2SO4; 4. KMnO4/NaOH/H2O; H3O+

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

E) 1. HNO3/H2SO4; 2. The formula of acetyl chloride, C H 3 C double bonded O C l and aluminum chloride, A l C l 3. ; 3. fuming H2SO4; 4. Br2/FeBr3; 5. excess H3O+/heat; 6. NaNO2/HCl/< 5°C; 7. H2SO4; 8. CuI

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

95) What reagents are needed to carry out the conversion shown?

C) 1. NaNO2/HCl/< 5°C; 2. CuBr; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. H3PO4

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

96) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

97) What is the predicted major product when p-toluidine reacts with sodium nitrite and hydrochloric acid at < 5°C, followed by treatment with o-ethylphenol?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

98) What is the predicted product of the reaction shown?

The SMILES string of the first possible product is CN(C)c2cccc(/N=N/c1ccccc1)c2 and the molecule has a benzene ring, in which C 1 is bonded to a nitrogen atom that is double bonded to a second nitrogen atom that is further bonded to a benzene ring and C 3 of the first benzene ring is bonded to a nitrogen atom that is further bonded to two methyl groups.

The SMILES string of the second possible product is CN(C)c2ccc(/N=N/c1ccccc1)cc2 and the molecule has a benzene ring, in which C 1 is bonded to a nitrogen atom that is double bonded to a second nitrogen atom that is further bonded to a benzene ring and C 4 of the first benzene ring is bonded to a nitrogen atom that is further bonded to two methyl groups.

The SMILES string of the third possible product is CN(C)c1ccccc1/N=N/c2ccccc2 and the molecule has a benzene ring, in which C 1 is bonded to a nitrogen atom that is double bonded to a second nitrogen atom that is further bonded to a benzene ring and C 2 of the first benzene ring is bonded to a nitrogen atom that is further bonded to two methyl groups.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

99) What is the predicted major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

100) What is the predicted major product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string Cc1ccc([N+]#[N-])cc1[Cl-] and the reactant has a benzene ring, in which C 1 is bonded to a nitrogen cation that is triple bonded to another nitrogen atom and it has chloride anion in the vicinity and the C 4 of the ring is bonded to a methyl group. The reactant reacts with dimethyl aniline.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

101) What reagents are needed to carry out the conversion shown?

In a chemical reaction, methoxy benzene reacts to form a product. The product formed has a SMILES string COc2ccc(N=Nc1ccc(Cl)cc1)cc2.

A) 1. Cl2/FeCl3; 2. HNO3/H2SO4; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. The structure of a molecule has the SMILES string COc1ccccc1 and the molecule has benzene ring, in which C 1 is bonded to a methoxy group.

B) 1. HB4; 2. H2O; 3. H2SO4; 4. Fe/HCl; 5. NaNO2/HCl/< 5°C; 5. The structure of a molecule has the SMILES string COc1ccccc1 and the molecule has benzene ring, in which C 1 is bonded to a methoxy group.

C) 1. HNO3/H2SO4; 2. Fe/HCl; 3. NaNO2/HCl/< 5°C; 4. The structure of a molecule has the SMILES string COc1ccccc1 and the molecule has benzene ring, in which C 1 is bonded to a methoxy group.

D) 1. HNO3/H2SO4; 2. Br2/FeBr3; 3. Fe/HCl; 4. NaNO2/HCl/< 5°C; 5. CH3OH/heat

Diff: 3

Learning Objective: 22.11 Predict the products for the reactions of aryl diazonium salts, including azo coupling

102) What is the predicted major product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string of c1cc[nH]c1 and the reactant has a pyrrole ring, in which N 1 is bonded to a hydrogen atom. The reactant reacts with molecular bromine at zero degree Celsius.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 23.12 Define heterocycle, and discuss the structure and reactions of pyrrole and pyridine and the structures of imidazole and pyrimidine

103) What is the predicted major product of the reaction shown?

In a chemical reaction, the reactant has a SMILES string of Cc1ccc[nH]1 and the reactant has a pyrrole ring, in which N 1 is bonded to a hydrogen atom and C 2 is bonded to a methyl group. The reactant reacts with molecular bromine at zero degree Celsius.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 23.12 Define heterocycle, and discuss the structure and reactions of pyrrole and pyridine and the structures of imidazole and pyrimidine

104) What is the predicted major product when pyridine is treated with a mixture of nitric acid and sulfuric acid?

A) 3-nitropyridine

B) 2-nitropyridine

C) 4-nitropyridine

D) 2,3-dinitropyridine

E) 4-aminopyridine

Diff: 2

Learning Objective: 23.12 Define heterocycle, and discuss the structure and reactions of pyrrole and pyridine and the structures of imidazole and pyrimidine

105) A compound with molecular formula C8H10BrN exhibits a singlet at δ 1.2 (2H), a triplet at δ 2.8 (2H), a triplet at δ 3.0 (2H), a doublet at δ 7.1 (2H) and a doublet at δ 7.4 (2H) in its 1H NMR spectrum. Its IR spectrum shows two medium absorption bands near 3400 cm-1. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13C NMR spectroscopy

106) A compound with molecular formula C8H19N exhibits a triplet at δ 0.9 (6H), a singlet at δ 1.1 (1H), a sextet at δ 1.3 (4H), a quintet at δ 1.4 (4H) and a triplet at δ 2.6 (4H) in its 1H NMR spectrum. Its IR spectrum shows a medium absorption band near 3400 cm-1. Its 13C NMR spectrum showed peaks at δ 13.7, δ 20.5, δ 30.4 and δ 49.2. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13C NMR spectroscopy

107) A compound with molecular formula C4H11N exhibits a triplet at δ 0.9 (3H), a doublet at δ 1.1 (3H), a quintet at δ 1.4 (2H), a singlet at δ 1.7 (2H) and a sextet at δ 2.8 (1H) in its 1H NMR spectrum. Its IR spectrum shows two medium absorption bands near 3400 cm-1. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13C NMR spectroscopy

108) A compound with molecular formula C7H17N exhibits a triplet at δ 1.0 (3H), a doublet at δ 1.1 (I=6), a multiplet at δ 2.0 (1H), a singlet at δ 2.3 (3H), a doublet at δ 2.3 (2H), and a quartet at δ 2.4 (2H) in its 1H NMR spectrum. Its 13C NMR spectrum showed peaks at δ 13.4, δ 20, δ 27.9, δ 39.3, δ 49.5 and δ 65.2. What is the structure for this compound?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13C NMR spectroscopy

109) A compound with molecular formula C6H15N displays the following IR, 1H NMR and 13C NMR spectra. What is a likely structure for this compound?

A carbon N M R is given, in which the horizontal axis ranges from 0 to 150 p p m, in increments of 10 units. The graph has a straight line at the following points: 10, the height of vertical axis; 22, three-fourth the height of vertical axis; 23, the height of vertical axis; 52, three-fourth the height of vertical axis.

SDBS

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13C NMR spectroscopy

110) A compound with molecular formula C8H11N displays the IR, 1H NMR and 13C NMR spectra shown. What is a possible structure for this compound?

A carbon N M R is given, in which the horizontal axis ranges from 0 to 150 p p m, in increments of 10 units. The graph has a straight line at the following points: 25, half the height of vertical axis; 50, half the height of vertical axis; 136, half the height of vertical axis; 137, the height of vertical axis; 139, the height of vertical axis; 142, half the height of vertical axis.

SDBS

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 22.13 Describe the signals produced by amines in IR, 1H NMR, and 13C NMR spectroscopy

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Chapter 22 Amines

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David R. Klein

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