Alcohols And Phenols Chapter 12 Exam Questions Klein

Organic Chemistry, 4e (Klein)

Chapter 12 Alcohols and Phenols

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

The structural formula of a compound has a six-carbon chain, in which C 2 is bonded to a hydroxyl group. C 3, C 4, and C 5 each is bonded to a methyl group.

A) 4-isopropyl-3,4-dimethyl-2-butanol

B) 2,3,4-trimethyl-4-pentanol

C) 1,1,2,3-tetramethyl-4-pentanol

D) 3,4,5-trimethyl-2-hexanol

E) 3,4,5,5-tetramethyl-2-pentanol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

2) What is the IUPAC name for isobutyl alcohol?

A) 2-methyl-1-propanol

B) 2-methyl-1-butanol

C) 1-methyl-1-propanol

D) 1,1-dimethyl-1-ethanol

E) 3-methyl-1-propanol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

The structural formula of a compound has a five-carbon chain, in which C 3 is bonded to a hydroxyl group and an ethyl group.

A) 1,1,1-triethylmethanol

B) 1,1-diethyl-1-propanol

C) 2-ethyl-3-pentanol

D) 3-ethyl-3-pentanol

E) t-heptanol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

4) What is the IUPAC name for t-butyl alcohol?

A) 1-butanol

B) 2-methyl-1-propanol

C) 2-methyl-2-propanol

D) 2-butanol

E) 1,1-dimethyl-1-ethanol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound that has a cyclopentane ring, in which C 1 is bonded to a hydroxyl group, O H and C 3 is bonded to an isopropyl group.

A) 1-isopropyl-4-cyclopentanol

B) 3-isopropylcyclopentanol

C) 1-isopropyl-3-cyclopentanol

D) 1-isopropyl-4-hydroxycyclopentane

E) None of these

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

6) What is the correct structure for 1-chloro-3-ethyl-2-pentanol?

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound that has a cyclohexane ring, in which C 1 is bonded to a hydroxyl group. C 4 is bonded to a bromine atom and C 6 is bonded to a methyl group.

A) 2-methyl-5-bromocyclohexanol

B) 3-bromo-2-methylcyclohexanol

C) 1-bromo-4-methylcyclohexanol

D) 4-bromo-6-methylcyclohexanol

E) 4-bromo-2-methylcyclohexanol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

The structural formula of a compound has a six-carbon chain, in which C 3 is double bonded to C 4. C 3 is bonded to a propanol group and C 4 is bonded to a methyl group.

A) 3-methyl-4-ethyl-3-hexen-6-ol

B) 4-ethyl-3-methyl-3,6-hexenol

C) 3-ethyl-4-methyl-3-hexen-1-ol

D) 3-methyl-4-(2-hydroxyethyl)-3-hexene

E) 3-(2-hydroxyethyl)-3-methyl-3-hexene

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound, which has a SMILES string of CC(C)(CC=C)O.

A) 4-penten-2-methyl-2-ol

B) 4-methyl-1-penten-2-ol

C) 2-methyl-4-penten-2-ol

D) 4-methyl-1-penten-4-ol

E) 4-hydroxy-4-methyl-1-pentene

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

The structure of the compound has a six-carbon chain, in which C 3 is triple bonded to C 4. C 2 is bonded to a hydroxyl group.

A) (R)-3-hexyn-2-ol

B) (S)-3-hexyn-2-ol

C) (R)-2-hexyn-4-ol

D) (S)-2-hexyn-4-ol

E) (S)-2-hydroxy-3-hexyne

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

11) What is the correct structure for 2,2-dibromo-1-methylcyclohexanol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

12) What is the correct structure for (E)-5,5-dimethyl-3-hepten-1-ol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound, which has a nine-carbon chain, in which C 7 is bonded to an isopropyl group and C 4 is bonded to a hydroxyl group.

A) 3-isopropyl-6-hydroxynonane

B) 4-hydroxy-6-ethyl-8-methyl-nonane

C) 7-isopropyl-4-nonanol

D) 7-ethyl-8-methyl-4-nonanol

E) 3-ethyl-6-hydroxy-nonane

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound, which has a seven-carbon chain, in which C 2 is bonded to a methyl group. C 3 is wedge bonded to a hydroxyl group and dash bonded to an ethyl group.

A) 5-hydroxy-5-ethyl-6-methylheptanol

B) 5-ethyl-5-hydroxy-6-methylheptanol

C) meso-3-ethyl-2-methyl-3-heptanol

D) (S)-3-ethyl-2-methyl-3-heptanol

E) (R)-3-ethyl-2-methyl-3-heptanol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound, which has a cyclopentane ring, in which C 2 is dash bonded to a bromine atom. C1 is wedge bonded to a methyl group and dash bonded to a hydroxyl group.

A) meso-2-bromo-1-methylcyclopentanol

B) (1R,2S)-2-bromo-1-methylcyclopentanol

C) (1S,2R)-2-bromo-1-methylcyclopentanol

D) (1R,1S)-2-bromo-1-methylcyclopentanol

E) (2R,2S)-2-bromo-1-methylcyclopentanol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound. The compound has a ten carbon chain, in which C 2 and C 8 each is bonded to a methyl group. C 3 is bonded to a hydroxyl group. C 7 is bonded to a cyclohexane ring.

A) 7-cyclohexyl-2,8-dimethyl-3-decanol

B) 1-(2-methylpropyl)-5-hydroxy-6-methyl-cyclohexane

C) 1-methyl-2-hydoxy-7-(1-methylpropyl)-7-cyclohexyl-heptane

D) 2,8-dimethyl-7-cyclohexyl-3-decanol

E) 7-cyclohexyl-2,8-methyl-3-decanol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

17) What is the structure for (E)-4,5,5-trimethyl-3-hepten-1-ol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

18) What is the structure for 5-chloro-2-propyl-1-heptanol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

19) What is the structure for 6-sec-butyl-7,7-dimethyl-4-decanol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound. The compound has an eight-carbon chain, in which C 2 is bonded to a methyl group. C 3 is bonded to a hydroxyl group and C 4 is bonded to an isobutyl group.

A) 2-methyl-4-(1-hydroxy-2-methylpropyl)-octane

B) 4-isobutyl-2-methyl-3-octanol

C) 2-methyl-4-isobutyl-octane

D) 4-isobutyl-3-hydroxymethanol

E) 4-butyl-1,6-dimethyl-5-octanol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

The structure of the compound has an eight-carbon chain, in which C 1 is triple bonded to C 2. C 3 is dash bonded to a hydroxyl group and wedge bonded to a hydrogen atom.

A) (R)-1-octyn-3-ol

B) (S)-1-octyn-3-ol

C) (R)-3-hydroxyalkyne

D) (S)-3-hydroxyalkyne

E) (R,S)-1-octyn-3-ol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

The structure of the compound has a ten-carbon chain, in which C 4 is bonded to a hydroxyl group and a propyl group. C 5 and C 6 is bonded to a propyl group.

A) 4,5,6-propyl-4-decanol

B) 4-hydroxy, 4,5,6-propyloctane

C) 4,5,6-dipropyl-4-decanol

D) 4-hydroxy, 4,5,6-propyldecane

E) 4,5,6-tripropyl-4-decanol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

The structure of the compound has a cyclohexane ring, in which C 1 is bonded to a hydroxyl group. C 3 is bonded to an ethyl group and double bonded to C 4.

A) 1-ethyl-3-hydroxy-1-cyclohexene

B) 3-ethyl-3-cyclohexenol

C) 1-ethyl-3-hydroxycyclohex-1-ene

D) 3-hydroxy-ethylcycylhexene

E) 3-ethyl-1-hydroxycyclohex-3-ene

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

24) What is the correct structure for 2-methylphenol?

An illustration shows five compounds represented by their bond-line structures. The first compound has a SMILES string of Cc1ccccc1O. The second compound has a SMILES string of CC1CCCCC1O. The third compound has a SMILES string of CC(c1ccccc1)O. The fourth compound has a SMILES string of CC1(CCCCC1)O. The fifth compound has a SMILES string of Cc1cccc(c1)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

25) What is the correct structure for 2-bromo-5-isopropylphenol?

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound. The compound has a SMILES string of c1cc(c(cc1Br)O)Br.

A) 3,4-dibromophenol

B) 2,4-dibromophenol

C) 2,5-dibromophenol

D) 3,6-dibromophenol

E) 2,6-dibromophenol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound. The compound has a benzene ring, in which C 1 is bonded to a hydroxyl group, O H, C 2 is bonded to a isopentyl group, and C 5 is bonded to an ethyl group.

A) 1-sec-butyl-5-ethylphenol

B) 1-sec-methylbutyl-5-ethylphenol

C) 2-sec-butyl-5-ethyltoluene

D) 2-tert-butyl-5-ethylhydroxybenzene

E) 2-sec-butyl-5-ethylphenol

Diff: 2

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

HOCH2CH2CH2OH

A) 1,2-butanediol

B) isopropyl alcohol

C) 1-propanol

D) 1,3-propanediol

E) 1,2-ethanediol

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

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

An illustration shows the bond-line structure of a compound. The compound has a SMILES string of C1C[C@@H]([C@H](C1)O)O.

A) cis-1,2-cyclopentanediol

B) meso-1,2-cyclopentanediol

C) (1R,2R)-1,2-cyclopentanediol

D) (1R,2S)-1,2-cyclopentanediol

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

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

30) What is the IUPAC name for the following compound?

An illustration shows the bond-line structure of a compound. The compound has a six-carbon chain , in which C 2 and C 4 each bonded to a hydroxyl group, O H, C 3 is bonded to a methyl group, and C 5 is bonded to an ethyl group.

A) 3,5-dimethyl-4,6-heptanediol

B) 3,5-dimethyl-2,4-heptanediol

C) 3,5-dimethyl-4,6-heptanol

D) 1-ethyl-3,5-hydroxy-3-methylhexane

E) 2,4-hydroxy-3,5-dimethylhexane

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

31) What is the structure for (2R,3S) -2-bromo-1,3-pentanediol?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

32) What is the formal name for rubbing alcohol?

A) methanol

B) 2-propanol

C) ethanol

D) 1-butanol

E) 1-propanol

Diff: 1

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

33) What is the formal name for grain alcohol?

A) methanol

B) 2-propanol

C) ethanol

D) 1-butanol

E) 1-propanol

Diff: 1

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

34) What is the formal name for wood alcohol?

A) methanol

B) 2-propanol

C) ethanol

D) 1-butanol

E) 1-propanol

Diff: 1

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

35) What is the formal name for the alcohol used in alcoholic drinks?

A) methanol

B) 2-propanol

C) ethanol

D) 1-butanol

E) 1-propanol

Diff: 1

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

36) What type of bonding is present between molecules of alcohol?

A) ion-ion

B) van der Waals forces

C) hydrogen bonding

D) ion-dipole

E) London dispersion

Diff: 1

Learning Objective: 12.1 Describe the structure, properties, and nomenclature of alcohols

37) Why does cyclohexanol have a pKa of 18 and phenol, despite its similarities in structure, have a pKa of 10?

A) Cycohexanol has a resonance-stabilized structure, which increases its stability and reduces the likelihood that it will react to form a conjugate base

B) Cycohexanol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation

C) Phenol has a resonance-stabilized conjugate base, which increases the stability of the base and favors its formation

D) Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and favors its formation

E) Phenol has a resonance-stabilized conjugate base, which decreases the stability of the base and inhibits its formation

Diff: 3

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

38) Rank the alcohols shown in decreasing order of acidity.

$An illustration shows three compounds represented by their bond-line structures. The first compound has a five-carbon chain, in which C 3 is bonded to a bromine atom, B r and C 5 is bonded to a hydroxyl group, O H. The second compound has a five-carbon chain, in which C 3 is bonded to a fluorine atom, F and C 5 is bonded to a hydroxyl group, O H. The third compound has a five-carbon chain, in which C 3 is bonded to an iodine atom, I and C 5 is bonded to a hydroxyl group, O H.$

A) II > I > III

B) I > II > III

C) I > III > II

D) III > I > II

E) III > II > I

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

39) Which one of the alcohols shown is the most acidic?

An illustration shows four compounds represented by their bond-line structures. The first compound has a SMILES string of C1CC(=CC(=O)C1)O. The second compound has a SMILES string of C1CCC(CC1)O. The third compound has a SMILES string of C1CC(CC(=O)C1)O. The fourth compound has a SMILES string of C1CC(=O)CCC1=O.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

40) Rank the alcohols shown in decreasing order of acidity.

A) II > I > III

B) I > II > III

C) I > III > II

D) III > I > II

E) III > II > I

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

41) Rank the alcohols shown in decreasing order of acidity.

A) II > I > III

B) I > II > III

C) I > III > II

D) III > I > II

E) III > II > I

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

42) Predict the product(s) for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a five-carbon chain, in which C 1 is bonded to a hydroxyl group and C 3 is bonded to a methyl group. The reactant reacts in presence of sodium atom, N a.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

43) Predict the product(s) for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CCC1CCCC(C1)(C)O that reacts in presence of lithium, L i.

A) I

B) II

C) III

D) I and II

E) III and IV

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

44) Predict the product for the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.2 Discuss the acidity of alcohols and phenols, including the three factors that determine relative acidity

45) Which set of reagents is necessary to carry out the following conversion?

An illustration shows a chemical reaction. The reactant is C H 3 C H 2 C H 2 (C single bond B r) H C H 3 yields a product C H 3 C H 2 C H 2 C H 2 C H 2 O H.

A) 1. NaBH4; 2. MeOH

B) 1. (CH)3COK; 2. BH3-THF; 3. H2O2/NaOH/H2O

C) 1. H3O+; 2. H2O

D) 1. (CH)3OH; 2. BH3-THF; 3. H2O2/NaOH/H2O

E) 1. (CH)3OH; 2. H2O2/NaOH/H2O

Diff: 2

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

46) Predict the product(s) for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CC1=CCCCC1 reacts in presence of borane tetrahydrofuran, B H 3 T H F in the first step followed by hydrogen peroxide, H 2 O 2 or sodium hydroxide, N a O H or water molecule, H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

47) Predict the product for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CC1=CCCC1 reacts in presence of oxymercuration, H g (O A c)2 and water molecule, H 2 O in the first step followed by sodium borohydride, N a B H 4 in the second step.

An illustration shows four compounds represented by their bond-line structure. The first compound has a SMILES string of CC1CCCC1O. The second compound has a SMILES string of CC1CCC(C1)O. The third compound has a SMILES string of CC1(CCCC1)O. The fourth compound has a cyclopentane ring, in which C 1 is bonded to a hydroxymethyl group, C H 2 O H.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

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

An illustration shows a chemical reaction, in which the reactant (E)-3-methyl-3-hexene yields trans-3-methyl-3-hexanol.

A) H3O+

B) 1. (CH)3COK; 2. BH3•THF; 3. H2O2/NaOH/H2O

C) 1. Hg(OAc)2, H2O; 2. NaBH4

D) A and B

E) A and C

Diff: 2

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

49) Predict the major product for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of C/C=C/C(C)C that reacts in presence of hydronium, H 3 O plus.

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of CCC(C(C)(C)C)O. The second compound has a SMILES string of CCC(O)C(C)C. The third compound has a SMILES string of CCC(C(C)(C)O)O. The fourth compound has a SMILES string of CCCC(C)(C)O. The fifth compound has a SMILES string of CCC(C(C)(C)O)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

50) Predict the product for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CCC1=CCCCC1 reacts in presence of oxymercuration, H g (O A c)2 and water molecule, H 2 O in the first step followed by sodium borodeuteride, N a B D 4 in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

51) Select the reagents suitable to carry out the conversion shown.

An illustration shows a chemical reaction. The reactant that has a SMILES string of c1ccc(cc1)CCBr yields a product. The product has a SMILES string of c1ccc(cc1)CCO.

A) NaOH/H3O+

B) NaOH

C) 1. Hg(OAc)2, H2O; 2. NaBH4

D) A and C

E) C and D

Diff: 3

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

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

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC(C)CCCCl yields a product. The product has a SMILES string of CC(C)CC(C)O.

A) NaOH/H2O

B) 1. NaOCH3; 2. H3O+

C) 1. (CH3)3COK; 2. BH3•THF; 3. H2O2/NaOH/H2O

D) 1. (CH3)3COK; 2. H3O+

E) B and D

Diff: 3

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

53) Identify the characteristics of the acid-catalyzed hydration of an alkene.

A) Markovnikov, with rearrangement possible

B) Markovnikov, with no rearrangement possible

C) anti-Markovnikov, with rearrangement possible

D) anti-Markovnikov, with no rearrangement possible

Diff: 1

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

54) Identify the characteristics of the hydroboration-oxidation of an alkene.

A) Markovnikov, with rearrangement possible

B) Markovnikov, with no rearrangement possible

C) anti-Markovnikov, with rearrangement possible

D) anti-Markovnikov, with no rearrangement possible

Diff: 1

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

55) Identify the characteristics of the oxymercuration-demercuration of an alkene.

A) Markovnikov, with rearrangement possible

B) Markovnikov, with no rearrangement possible

C) anti-Markovnikov, with rearrangement possible

D) anti-Markovnikov, with no rearrangement possible

Diff: 1

Learning Objective: 12.3 Discuss the reactions used in the preparation of alcohols by substitution or addition

56) What are the oxidation states of carbon atoms I and II in the compound shown?

The bond-line structure of a compound has eight-carbon chain, in which C 2 and C 7 are each double bonded to an oxygen atom, and C 8 is bonded to a hydrogen atom. An arrow labeled, 1 points toward C 2 and an arrow labeled, 2 points toward C 7.

A) I. +1, II. +2

B) I. +2, II. +2

C) I. +1, II. +3

D) I. +3, II. +2

E) I. +2, II. +1

Diff: 1

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

57) What are the oxidation states of carbon atoms I and II in the reaction shown?

An illustration shows a chemical reaction. The reactant is C H 3 (C double bond O) H yields a product C H 3 (C double bond O) O H. An up arrow points towards the carbon atom double bonded to oxygen atom in reactant and is labeled 1. An up arrow points towards the carbon atom double bonded to oxygen atom in product and is labeled 2.

A) I. +1, II. +2

B) I. +2, II. +2

C) I. +1, II. +3

D) I. +3, II. +2

E) I. +2, II. +1

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

58) For the following conversion, has the starting material has been oxidized, reduced, a combination, or neither?

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC1CCCC1O yields a product. The product has a SMILES string of CC1CCCC1=O.

A) oxidized

B) reduced

C) oxidized and then reduced

D) reduced and then oxidized

E) neither oxidized nor reduced

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

59) For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither.

An illustration shows a chemical reaction. The reactant that has a SMILES string of C1CCC=CC1 yields a product. The product has a SMILES string of C1CCC(C(C1)Cl)Cl.

A) oxidized

B) reduced

C) oxidized and then reduced

D) reduced and then oxidized

E) neither oxidized nor reduced

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

60) For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCC(C)O yields a product. The product has a SMILES string of CCC(C)OCC.

A) oxidized

B) reduced

C) oxidized and then reduced

D) reduced and then oxidized

E) neither oxidized nor reduced

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

61) For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CC1=CCCCC1 yields a product. The product has a SMILES string of CC(=O)CCCCC=O.

A) oxidized

B) reduced

C) oxidized and then reduced

D) reduced and then oxidized

E) neither oxidized nor reduced

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

62) For the following conversion, identify if the starting material has been oxidized, reduced, a combination, or neither.

An illustration shows a chemical reaction. The reactant that has a SMILES string of CCCCC(=O)O yields a product. The product has a SMILES string of CCCCC(=O)OC.

A) oxidized

B) reduced

C) oxidized and then reduced

D) reduced and then oxidized

E) meither oxidized nor reduced

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

63) What is the most likely product of the reaction shown?

An illustration shows an incomplete chemical reaction. The reactant is C H 3(C double bond O) C H 2 C H 2 C H 3 reacts in presence of sodium borohydride, N a B H 4 and methanol, C H 3 O H.

The condensed structural formula of a compound is C H 3 (C double bond O) C H 2 O C H 2 C H 3.

The condensed structural formula of a compound is C H 3 C H O H C H 2 C H 2 C H 3.

The condensed structural formula of a compound is C H 3 (C double bond O) C H 2 C H 2 C H 2 O H.

The condensed structural formula of a compound is C H 3 C H O H C H 2 C H 2 C H 2 O H.

The condensed structural formula of a compound is C H 2 O H C H 2 C H 2 C H 2 C H 3.

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

64) Predict the product for the reaction shown.

An illustration shows an incomplete chemical reaction in which the reactant has a SMILES string of C1CC(CC=C1)C=O reacts in presence of sodium borohydride, N a B H 4 or methanol, C H 3 O H.

An illustration shows four compounds represented by their bond-line structure. The first compound has a SMILES string of C1CC(CC=C1)CO. The second compound has a SMILES string of C1CC(CC=C1)C(=O)O. The third compound has a SMILES string of C1CCC(CC1)CO. The fourth compound has a cyclohexane ring, in which C 1 is bonded to a carbon atom which is further bonded to two hydroxyl groups.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

65) Which one of the compounds shown gives 5-methyl-3-heptanol when LiAlH4 is added followed by water?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

66) What reagents can be used to carry out the following conversion?

An illustration shows a chemical reaction. The reactant is H (C triple bond C) C H 2 C H 2 C H 3 yields a product C H 3 (C single bond O H) H C H 2 C H 2 C H 3.

A) 1. Na, NH3; 2) 2 H3O+

B) 1. H2/Ni2B (OR Na, NH3); 2 H3O+

C) 1. H3O+/ HgSO4; 2. NaBH4/CH3OH

D) A and B

E) A, B, and C

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

67) Predict the product for the reaction shown.

An illustration shows an incomplete chemical reaction in which the reactant has a SMILES string of C1CC(CC=C1)C=O reacts in presence of H 2 Pd.

A) I

B) II

C) III

D) IV

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

68) Predict the product for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a cyclohexane ring, in which C 1 is bonded to a C O O C H 3 and C 3 is double bonded to an oxygen atom. The reactant reacts in presence of sodium borohydride, N a B H 4 and water molecule, H 2 O.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

69) Predict the product for the following reaction.

An illustration shows an incomplete chemical reaction. The reactant has a cyclohexane ring, in which C 1 is bonded to a C O O C H 3 and C 3 is double bonded to an oxygen atom. C 1 is double bonded to C 2. The reactant reacts in presence of lithium aluminum hydride, L i A l H 4 and water molecule, H 2 O.

A) I

B) II

C) III

D) I and II

E) I and III

Diff: 3

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

70) Predict the product for the following reaction.

An illustration shows three compounds represented by their bond-line structure. The first compound has a SMILES string of C1CCC(C1)CCO. The second compound has a SMILES string of CC(O)CC1CCCC1. The third compound has a cyclopentane ring, in which C 1 is bonded to three-carbon side chain where C 1 is bonded to a hydroxyl group O H and C 2 is bonded to a methyl group.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 2

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

71) Provide the reactant (A) for the reaction shown.

An illustration shows a chemical reaction, in which a reactant A reacts in presence of lithium aluminum hydride, L i A l H 4 in the first step followed by water molecule, H 2 O in the second step to yield the product 5-methyl-3-heptanol.

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of CCC(C)CC(=O)CC. The second compound has a SMILES string of CCC(C)CC=O. The third compound has a SMILES string of CCC(C)CC(=O)C. The fourth compound has a SMILES string of CCCC(C)CC=O. The fifth compound has a SMILES string of CCCC(=O)CC(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 1

Learning Objective: 12.4 Discuss the reactions used in the preparation of alcohols by reduction

72) What reagents are suitable to carry out the following conversion?

An illustration shows a chemical reaction, in which the reactant cyclohexene yields s-1,2-cyclohexanediol.

A) KMnO4, NaOH,H2O,cold

B) KMnO4, H3O+, 75°C

C) H2SO4, heat

D) 1. mCPBA 2. H3O+

E) none of these

Diff: 2

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

73) What are the likely product(s) of the reaction shown.

An illustration shows a chemical reaction. The reactant 3-hexyne reacts in presence of the following compounds as shown in two forward arrows. The first arrow has H 2 and N I 2 B above the arrow. The second arrow has osmium tetroxide, O s O 4 above the arrow and sodium bisulfite, N a H S O 3 below the arrow.

A) I

B) II

C) III

D) I and II

E) None of these

Diff: 2

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

74) What reagents are suitable to carry out the conversion shown?

An illustration shows a chemical reaction, in which the reactant cyclohexene yields trans-1,2-cyclohexanediol.

A) KMnO4, NaOH,H2O

B) KMnO4, H3O+, 75°C

C) H2SO4, heat

D) 1. mCPBA; 2. H3O+

E) none of these

Diff: 2

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

75) Correctly label structures A, B, C, and D from the reaction sequence below.

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

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

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

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

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

Diff: 3

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

76) What is the likely product of the reaction shown?

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of O=C(CCCC=O)C1CCCCC1 reacts in presence of excess sodium borohydride, N a B H 4 or methanol, C H 3 O H.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

77) What is the likely product of the reaction shown?

An illustration shows an incomplete chemical reaction. The reactant has a cyclopentane ring, in which C 1 is wedge bonded to a methyl group and both C 1 and C 2 are dash bonded to a common oxygen atom reacts in presence of a hydronium ion H 3 O plus.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 2

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

78) What reagent(s) are suitable to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of CC/C=C/CC yields a product. The product has a SMILES string of CC[C@H]([C@H](CC)O)O.

A) 1. mCPBA; 2. H3O+

B) 1. mCPBA; 2. NaOH/H2O

C) H2SO4, heat

D) A and B

E) B and C

Diff: 3

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

79) What reagent(s) are suitable to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of CC1=CCCCC1 yields a product. The product has a SMILES string of OCCCCCC(O)C.

A) 1. O3; 2.1 equivalent of NaBH4/CH3OH

B) 1. O3; 2. CH3)2S; 3. H3O+

C) 1. O3; 2. (CH3)2S; 3. excess NaBH4/CH3OH

D) A and B

E) B and C

Diff: 3

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

80) Predict the product(s) for the reaction shown.

An illustration shows a chemical reaction, in which the reactant has a SMILES string of CC(=O)C1CC(=O)OC1 reacts in presence of excess lithium aluminum hydride, L i A l H 4 in the first step followed by water molecule, H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.5 Describe the functional group transformations that can be used to synthesize diols

81) What is the likely product of the reaction sequence shown?

An illustration shows a chemical reaction, in which the reactant has a SMILES string of CCC(C)C(=O)C reacts in presence of C H 3 C H 2 M g B r in the first step followed by water molecule, H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

82) What is the most likely product for the reaction sequence given.

An illustration shows a chemical reaction. The reactant has a SMILES string of CCC(C)C(C)CCBr reacts in presence of the following compounds as shown in two forward arrows. The first arrow has an M g and ether above the arrow. The second arrow has a compound that has a SMILES string of CCC=O above the arrow and a water molecule, H 2 O below the arrow.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

83) What reagent(s) are suitable to carry out the following conversion?

An illustration shows a chemical reaction. The reactant has a SMILES string of COC(=O)C1CCCC1 yields a product. The product has a SMILES string of CC(C)(C1CCCC1)O.

A) 1. 1 equivalent of CH3MgBr; 2. H2O

B) 1. excess CH3Br/ether; 2. H2O

C) 1. CH3MgBr; 2. H3O+

D) 1. excess CH3MgBr/ether; 2. H2O

E) 1. CH3CH2MgBr/ether; 2. H2O

Diff: 2

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

84) Predict the product for the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CC(C)C(=O)c1ccccc1 that reacts in presence of Grignard reagent, C H 3 C H 2 C H 2 M g B r or ether in the first step followed by water molecule, H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) None of these

Diff: 2

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

85) Predict the product for the following reaction.

An illustration shows an incomplete chemical reaction along with five possible structures for product labeled 1 through 5 (in Roman Numerals).
In the reaction, the reactant that has a SMILES string of c1ccc(cc1)Br reacts in the presence of M g and ether, followed by a compound that has a SMILES string of C=O in the first step and water molecule, H 2 O, in the second step.

The five possible structures for the product are as follows:
Structure 1 has a SMILES string of c1ccc(cc1)CO.
Structure 2 has a SMILES string of CC(=O)c1ccccc1.
Structure 3 has a SMILES string of c1ccc(cc1)CBr.
Structure 4 has a benzene ring, in which C 1 is bonded to a methylene group which is further bonded to M g B r.
Structure 5 has a SMILES string of C1CCC(CC1)Br.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

86) Which Grignard reaction shown could be used to could prepare the alcohol shown?

An illustration of a compound represented by the bond-line structure. The compound has a SMILES string of c1ccc(cc1)CO.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 2

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

87) Which Grignard reaction shown could be used to prepare the alcohol shown?

The bond-line structure of a compound has a cyclohexane ring, in which C 1 is bonded to a four-carbon side chain. The C 2 of the side chain is bonded to a hydroxyl group, O H and C 3 is bonded to a methyl group.

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

88) Which Grignard reaction shown could be used to prepare the alcohol shown?

The bond-line structure of a compound has a SMILES string of CCC(Cc1ccccc1)(CC(C)C)O.

A) I

B) II

C) III

D) I and II

E) I, II, and III

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

89) What reagents are appropriate to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of CCCC=C, which yields a product that has a SMILES string of CCCC(C)CO.

A) 1. Br2; 2. Mg/ether, 3. The bond-line structure of a compound has a SMILES string of C=O. ; 4. H3O+

B) 1. HBr, 2. ether, 3. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom and single bonded to a hydrogen atom and single bonded to C H 2 C H 3. ; 4. H2O

C) 1. HBr, 2. Mg/ether, 3. The bond-line structure of a compound has a SMILES string of C=O. ; 4. H2O

D) 1. Br2, 2. Mg/ether, 3. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom and single bonded to a hydrogen atom and single bonded to C H 2 C H 3. ; 4. H2O

E) 1. HBr, 2. Mg/ether, 3. The bond-line structure of a compound has a SMILES string of C1CCC(CC1)O. ; 4. H3O+

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

90) What reagent(s) are necessary to prepare 1-isopropylcyclopentanol using a Grignard reaction?

A) I

B) II

C) III

D) I and II

E) II and III

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

91) What is the likely product of the reaction shown?

An illustration shows an incomplete chemical reaction. The reactant has a benzene ring, in which C 1 is bonded to a carbon atom that is double bonded to an oxygen atom and further single bonded to O C H 3. The reactant reacts in presence of excess C H 3 C H 2 C H 2 M g B r and water molecule H 2 O.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

92) What is the most likely product of the following reaction?

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of C1CCOC(=O)C1 reacts in presence of excess Grignard reagent C H 3 C H 2 M g B r in the first step followed by water molecule H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

93) What is the most likely product of the following reaction?

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of COC(=O)OC reacts in presence of excess Grignard reagent C H 3 C H 2 M g B r in the first step followed by water molecule H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

94) What is the best description of the curved arrow mechanism of the first step of the reaction shown?

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of COC(=O)OC reacts in presence of excess Grignard reagent, C H 3 C H 2 M g B r in the first step followed by water molecule, H 2 O in the second step.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.6 Describe Grignard reagents and explain how they are used in the production of alcohols

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

An illustration shows a chemical reaction. The reactant has a SMILES string of C(CCO)CCBr that yields a product that has a SMILES string of CC(C)(CCCCCO)O.

A) 1. (CH3)3SiCl / (CH3CH2)3N; 2. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom. ; 2. H2O; 4. TBAF

B) 1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg/ether; 3. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom. ; 4. H2O; 5. TBAF

C) 1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg/ether; 3. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom. ; 4. H2O

D) 1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg/ether; 3. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom and single bonded to two hydrogen atoms. ; 4. H2O; 5. TBAF

E) 1. (CH3)3SiCl / (CH3CH2)3N; 2. Mg; 3. The bond-line structure of a compound has a central carbon atom double bonded to an oxygen atom and single bonded to two hydrogen atoms. ; 4. H2O

Diff: 3

Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome

96) What reagents are suitable to carry out the following conversion?

An illustration shows a chemical reaction. The reactant has a SMILES string of C1CC(=O)CCC1CO that yields a product. The product has a cyclohexane ring, in which C 1 is bonded to a hydroxyl group, O H and C 1 is also bonded to a carbon atom which is further bonded to a cyclopentane. C 4 is bonded to a carbon atom which is further bonded to a hydroxyl group, O H.

A) 1. (CH3)3SiCl / (CH3CH2)3N; 2. The bond-line structure of a compound has a SMILES string of OCC1CCCC1.

; 3. H2O; 4. TBAF

B) 1. (CH3)3SiCl; 2. The bond-line structure of a compound has a cyclopentane ring, in which C 1 is bonded to a methylene group which is further bonded to M g B r.

; 3. H2O

C) 1. (CH3)3SiCl / (CH3CH2)3N; 2. The bond-line structure of a compound has a cyclopentane ring, in which C 1 is bonded to a methylene group which is further bonded to M g B r.

; 3. H2O; 4. TBAF

D) 1. (CH3)3SiCl / (CH3CH2)3N; 2. The bond-line structure of a compound has a SMILES string of C1CCC(C1)CBr.

; 3. H2O; 4. TBAF

E) 1. (CH3)3SiCl / (CH3CH2)3N; 2. The bond-line structure of a compound has a cyclopentane ring, in which C 1 is bonded to a methylene group which is further bonded to M g B r. C 1 is double bonded to C 2.

; 3. H2O; 4. TBAF

Diff: 3

Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome

97) For the following reaction sequence, what are the correct structures of products A through D?

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

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

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

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

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

Diff: 3

Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome

98) What is the most likely product for the following reaction sequence?

A) 2,4-heptanediol

B) 1,4-heptanediol

C) 2,5-octanediol

D) 1,5-octanediol

E) none of these

Diff: 3

Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome

99) What reagents are suitable to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of C#CCCCO that yields a product that has a SMILES string of C(#CCCCO)CCC.

A) 1. (CH3)3SiCl / (CH3CH2)3N; 2. CH3CH2CH2Br; 3.TBAF

B) 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2CH2Br

C) 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2CH2Br; 4.TBAF

D) 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2Br

E) 1. (CH3)3SiCl / (CH3CH2)3N; 2. NaNH2; 3. CH3CH2CH2Br; 4.TBAF

Diff: 3

Learning Objective: 12.7 Explain how the incompatibility between a hydroxyl group and a Grignard reagent is overcome

100) What are the correct structures for the products represented by A, B, and C?

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

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

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

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

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

Diff: 3

Learning Objective: 12.8 Describe the industrial synthesis of phenols

101) 2-Methyl-2-butanol reacts with hydrogen bromide via a(n) ________.

A) SN1 mechanism

B) SN2 mechanism

C) E1 mechanism

D) E2 mechanism

E) None of these.

Diff: 1

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

102) 3-Methyl-1-butanol reacts with hydrogen bromide via a(n) ________.

A) SN1 mechanism

B) SN2 mechanism

C) E1 mechanism

D) E2 mechanism

E) None of these.

Diff: 1

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

103) 3-Methyl-1-butanol reacts with thionyl chloride via a(n) ________.

A) SN1 mechanism

B) SN2 mechanism

C) E1 mechanism

D) E2 mechanism

E) None of these.

Diff: 1

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

104) Which of the following reactions could be used to synthesize 1-bromopentane?

I CH3CH2CH2CH=CH2 + HBr →

II CH3CH2CH2CH2CH2OH + PBr3 →

III CH3CH2CH2CH2CH2OH + NaBr →

IV CH3CH2CH2CH2CH2OH + Br2 →

V CH3CH2CH2CH=CH2 + Br2 →

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

105) Which reagents are suitable to convert 3-methyl-2-butanol to 2-bromo-3-methylbutane.

A) conc. HBr

B) Br2

C) NaBr, H2SO4

D) PBr3

E) HBr, peroxide

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

106) Predict the product for the following reaction.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of O[C@@H]1C[C@H](C)CC1 reacts in presence of phosphorus tribromide, P B r 3.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

107) Identify the product of the reaction shown.

An illustration shows a chemical reaction. The reactant has a SMILES string of CCCC(C)C(C)O reacts in presence of hydrogen bromide, H B r.

A) I

B) II

C) III

D) IV

E) I and II

Diff: 3

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

108) What is the most likely major product of the reaction shown?

A) I

B) II

C) III

D) IV

E) I and IV

Diff: 3

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

109) What is the most likely product of the reaction shown.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CC[C@@H](CCC(C)C)O reacts in presence of thionyl chloride SOCl2 and pyridine.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

110) What is the most likely major product for the reaction shown?

An illustration shows an incomplete chemical reaction. The reactant has a cyclohexane ring, in which C 1 is wedge bonded to a hydroxyl group, O H and dash bonded to a hydrogen atom. C 2 is wedge bonded to a methyl group, C H 3 and dash bonded to a hydrogen atom. The reactant reacts in presence of T s C l and pyridine in the first step and sodium iodide, N a I in the second step.

A) I

B) II

C) III

D) IV

E) I and III

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

111) What is the most likely product when cis-3-methylcyclopentanol is treated with TsCl/pyridine followed by sodium bromide.

A) trans-1-bromo-3-methylcyclopentane

B) cis-1-bromo-3-methylcyclopentane

C) 1-methylcyclopentene

D) 2-methylcyclopentene

E) 3-methylcyclopentene

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

112) The reaction between 2-methyl-2-pentanol and sulfuric acid to yield 2-methyl-2-pentene proceeds via a(n) ________.

A) SN1 mechanism

B) SN2 mechanism

C) E1 mechanism

D) E2 mechanism

E) None of these.

Diff: 1

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

113) Explain why the following reaction will not produce an alcohol as product.

An illustration shows a chemical reaction. The reactant has a SMILES string of CCCC(C)(C)Cl reacts in presence of sodium hydroxide, N a O H to yield a product. The product has a SMILES string of CCCC(C)(C)O and is labeled not produced.

A) C l is not a good leaving group and therefore cannot be replaced by hydroxide.

B) The primary methyl group is not sufficiently reactive to allow the reaction to begin.

C) Steric hindrance at the tertiary halide prevents hydroxide from acting as a nucleophile in an SN2 reaction.

D) NaOH is not a sufficiently strong base to initiate the reaction.

E) Tertiary halides are not reactive.

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

114) What is the most likely major product of the following reaction.

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of CC1(CCCCC1)O reacts in presence of T s C l or pyridine in the first step followed by sodium ethoxide, C H 3 C H 2 O N a in the second step.

An illustration shows five compounds represented by their bond-line structures. The first compound has a SMILES string of C1CCC(=CC1)O. The second compound has a SMILES string of CC1CCCCC1. The third compound has a SMILES string of C1CCC(CC1)O. The fourth compound has a SMILES string of C1CCC=CC1. The fifth compound has a SMILES string of CC1=CCCCC1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

115) What is the most likely major product for the reaction shown.

$An illustration shows five compounds represented by their bond-line structures. The first compound has a SMILES string of CC1CCCCC1C. The second compound has a SMILES string of CC1CCCCC1(C)C. The third compound has a SMILES string of O\C1=C(/C)CCCC1. The fourth compound has a SMILES string of CC1=C(CCCC1)C. The fifth compound has a SMILES string of CC1(CCCCC1(C)C)C.$

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

116) Provide the reagent(s) necessary to convert cyclohexanol to cyclohexane.

A) 1. H2SO4, heat; 2. H2/Pd

B) 1. H2SO4; 2. CH3CH2ONa; 3. H2/Pd

C) 1. TsCl/pyridine; 2. CH3CH2ONa; 3. H2/Pd

D) A and B

E) A and C

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

117) Which example best describes the stepwise curved arrow mechanism for the first step of the reaction shown?

A) I

B) II

C) III

D) IV

E) I or II

Diff: 3

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

118) Predict the product of the reaction shown.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.9 Describe the substitution and elimination reactions of alcohols

119) What is the likely product of the following reaction?

An illustration shows an incomplete chemical reaction. The reactant 2 hexanol reacts in presence of pyridinium cholorochromate, P C C and dichloromethane, C H 2 C l 2.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

120) What are the appropriate reagents to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a cyclohexane ring, in which C 1 is bonded to a hydroxyl group, O H and C 4 is bonded to a methyl group. C 3 is double bonded to C 4. The reactant yields a product that has a SMILES string of CC1=CCC(=O)CC1.

A) KMnO4/NaOH/H2O

B) Na2Cr2O7/H2SO4/H2O

C) H2, Pt

D) Br2, CCl4

E) None of these

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

121) Predict the product for the following reaction.

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of CCCC(O)O. The second compound has a SMILES string of CCCC(C)O. The third compound has a SMILES string of CCC=C(C)C. The fourth compound has a SMILES string of CCCC(=O)C. The fifth compound has a SMILES string of CCCC(C)C.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

122) What is the most likely product of the following reaction?

An illustration shows an incomplete chemical reaction. The reactant has a SMILES string of c1ccc(cc1)CCO reacts in presence of pyridinium chlorochromate, P C C and dichloromethane, C H 2 C l 2.

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of c1ccc(cc1)CC=O. The second compound has a SMILES string of c1ccc(cc1)CO. The third compound has a SMILES string of CC(C)Cc1ccccc1. The fourth compound has a SMILES string of C/C=C/c1ccccc1. The fifth compound has a SMILES string of C=CCc1ccccc1.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

123) What are the appropriate reagents to carry out the following conversion?

An illustration shows a chemical reaction. The reactant has a SMILES string of C/C=C/CCCO yields a product that has a SMILES string of C/C=C/CCC(=O)O.

A) KMnO4/NaOH/H2O

B) Na2Cr2O7/H2SO4/H2O

C) PCC/CH2Cl2

D) Br2, CCl4

E) None of these

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

124) What are the appropriate reagents to carry out the following conversion?

An illustration shows a chemical reaction. The reactant has a SMILES string of C/C=C/CCCO yields a product that has a SMILES string of C/C=C/CCC(=O)O.

A) KMnO4/NaOH/H2O

B) Na2Cr2O7/H2SO4/H2O

C) PCC/CH2Cl2

D) Br2, CCl4

E) None of these

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

125) What is the most likely product of the following reaction?

A) I

B) II

C) III

D) IV

E) III and IV

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

126) What is the most likely product of the following reaction?

An illustration shows an incomplete chemical reaction. The reactant that has a SMILES string of CCC1(CCCCC1)O reacts in presence of pyridinium chlorochromate P C C and dichloromethane C H 2 C l 2.

An illustration shows four compounds represented by their bond-line structure. The first compound has a SMILES string of CC1(CCCCC1)O. The second compound has a SMILES string of C1CCC(=O)CC1. The third compound has a SMILES string of C=CC1(CCCCC1)O. The fourth compound has a SMILES string of C1CCC=CC1.

A) I

B) II

C) III

D) IV

E) No reaction.

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

127) What is the most likely product of the following reaction?

An illustration shows an incomplete chemical reaction. The reactant cis 4 methylcyclohexanol reacts in presence of pyridinium chlorochromate, P C C and dichloromethane, C H 2 C l 2.

An illustration shows four compounds represented by their bond-line structure. The first compound has a SMILES string of CC1CCC(CC1)O. The second compound has a SMILES string of CC1CCC(CC1)C. The third compound has a SMILES string of CC1CCC(=CC1)O. The fourth compound has a SMILES string of CC1CCC(=O)CC1.

A) I

B) II

C) III

D) IV

E) No reaction

Diff: 2

Learning Objective: 12.10 Describe the oxidation reactions of alcohols

128) Catalysts in living systems are called ________.

A) hormones

B) enzymes

C) reactive oxygen species

D) cytoskeletal proteins

E) lysosomal products

Diff: 1

Learning Objective: 12.11 Discuss the functions of NAD+ and NADH in biological systems

129) NADH servers as a ________ delivery agent in living organisms.

A) oxygen

B) hydride

C) hydroxide

D) proton

E) ozone

Diff: 1

Learning Objective: 12.11 Discuss the functions of NAD+ and NADH in biological systems

130) What is the most likely product of the following reaction?

A) I

B) II

C) III

D) IV

E) No reaction

Diff: 2

Learning Objective: 12.12 Name the oxidation product of a phenol and explain the importance of this product

131) What is the structure for the final product (D), in the reaction sequence shown?

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of CCC(C)C(=O)C. The second compound has a SMILES string of CC(C)CO. The third compound has a SMILES string of CCC(C)C(=O)C. The fourth compound has a SMILES string of CCC(C)O. The fifth compound has a SMILES string of CCC(C)C(C)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

132) Which series correctly shows structures A, B, and C labeled correctly and in order?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

133) What is the structure for the final product, (E), in the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

134) Of the choices, which correctly matches a structure with one of the products in the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

135) What is the structure for product (A) in the reaction sequence shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of CCC(C)O reacts in presence of the following compounds shown in three forward arrows to yield a product A. The first forward arrow has phosphorus tribromide P B r 3 above the arrow. The second arrow has M g above the arrow and ether below the arrow. The third arrow has deuterium oxide D 2 O above the arrow.

A) CH3CH2CH2CH3

B) CH3CH2CHDCH3

C) CH3CH2CHODCH3

D) CH3CH2CH2CH2OD

E) CH3CH2CH2CH2D

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

136) What reagents are appropriate to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of C1CCC(CC1)O yields a product that has a SMILES string of CCC(=O)C1CCCCC1.

A) 1. PBr3; 2. Mg/ether; 3. The bond-line structure of a compound has a SMILES string of CCC=O. ; 4. H2O; 5. PCC/CH2Cl2

B) 1. PBr3; 2. Mg/ether; 3. The bond-line structure of a compound has a SMILES string of CCC=O. ; 4. H2O

C) 1. PBr3; 2. Mg/ether; 3. The bond-line structure of a compound has a SMILES string of CCC=O. ; 4. PCC/CH2Cl2

D) 1. BrMg/ether; 2. The bond-line structure of a compound has a SMILES string of CCC=O. ; 3. H2O; 4. PCC/CH2Cl2

E) 1. PBr3; 2. Mg/ether; 3. The bond-line structure of a compound has a SMILES string of CCC=O. ; 4. NaBH4/CH3OH

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

137) Which example shows the best choice of reactant for the first step in the synthesis shown?

In a chemical reaction, the reactant has a SMILES string of C1CCCCC1 that yields a product with a SMILES string of C1CCC(CC1)C=O.

A) Cl2, hv

B) H3O+

C) 1. CH3MgBr; 2. H2O

D) H2SO4, heat

E) PCC, CH2Cl2

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

138) What is the likely product of the reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

139) What is the likely product for the following reaction sequence shown?

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

140) What is the stepwise synthesis for the reaction shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of CC1CCCCC1 yields a product that has a SMILES string of CC1CCCCC1=O.

A) 1. Br2, hν; 2. BH3-THF followed by H2O2/NaOH/H2O; 3. CH3CH2ONa; 4. PCC/CH2Cl2

B) 1. Br2, hv; 2. PCC/CH2Cl2; 3. CH3CH2ONa; 4. BH3-THF followed by H2O2/NaOH/H2O;

C) 1. Br2, hv; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2

D) 1. CH3CH2ONa; 2. Br2, hv; 3. BH3-THF followed by H2O2/NaOH/H2O; 4. PCC/CH2Cl2

E) 1. BH3-THF followed by H2O2/NaOH/H2O; 2. Br2, hv; 3. CH3CH2ONa; 4. PCC/CH2Cl2

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

141) What reagents are appropriate to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of C1CCCCC1 yields a product that has a SMILES string of C1CCC(=O)C(=O)C1.

A) 1. CH3CH2Ona; 2. KMnO4/NaOH; 3. H2O; 4. excess PCC/CH2Cl2

B) 1. Cl2/hv; 2. CH3CH2Ona; 3. KMnO4/NaOH/H2O; 4. excess PCC/CH2Cl2

C) 1. Cl2/hv; 2. CH3CH2Ona; 3. KMnO4/NaOH/H2O; 4. 1 equivalent PCC/CH2Cl2

D) 1. CH3CH2Ona; 2. KMnO4/NaOH/H2O; 3. excess PCC/CH2Cl2

E) 1. Cl2/hv; 2. KMnO4/NaOH/H2O; 3. H3O+; 4. excess PCC/CH2Cl2

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

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

An illustration shows a chemical reaction. The reactant has a SMILES string of CC(=O)CCCO yields a product that has a SMILES string of CC(C)(O)CCCO.

A) 1. (CH3)3SiCl/ (CH3CH2)3N; 2. CH3MgBr; 3. H3O+

B) 1. (CH3)3SiCl/ (CH3CH2)3N; 2. CH3MgBr

C) 2. CH3MgBr; 2. H3O+

D) 1. (CH3)3SiCl/ (CH3CH2)3N; 2. H3O+

E) 1. (CH3)3SiCl/ (CH3CH2)3N; 2. KOH; 3. CH3MgBr; 4. H3O+

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

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

An illustration shows a chemical reaction. The reactant has a SMILES string of c1ccc(cc1)CCCBr yields a product that has a SMILES string of c1ccc(cc1)CCC(=O)O.

A) 1. NaOH; 2. H2O

B) 1. NaOH; 2. H2SO4; 3. H2O

C) 1. Na2Cr2O7/H2SO4; 2. H2O

D) 1. NaOH; 2. Na2Cr2O7/H2SO4/H2O

E) 1. KOH; 2. Na2Cr2O7; 3. NaOH

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

144) Choose the best stepwise synthesis to carry out the conversion shown.

An illustration shows a chemical reaction. The reactant has a SMILES string of CC1CCCC1 yields a product that has a SMILES string of CC1CCCC1C.

A) 1. Br2, hv; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O;

4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4/heat;

7. H2/Lindlar's catalyst.

B) 1. Br2, hv; 2. BH3-THF followed by H2O2/NaOH/H2O; 3. CH3CH2ONa;

4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4/heat; 7. H2/Pd.

C) 1. Br2, hv; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O;

4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4/heat; 7. H2/Pd.

D) 1. HBr; 2. CH3CH2ONa; 3. BH3-THF followed by H2O2/NaOH/H2O;

4. PCC/CH2Cl2; 5. CH3MgBr followed by H2O; 6. H2SO4; 6. H2/Pd.

E) 1. CH3CH2ONa; 2. BH3-THF followed by H2O2/NaOH/H2O; 3. PCC/CH2Cl2;

4. CH3MgBr followed by H2O; 5. H2SO4/heat; 6. H2/Pd.

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

145) Of the choices below, which is not a component of the stepwise synthesis needed to carry out the conversion shown?

An illustration shows a chemical reaction. The reactant has a SMILES string of CCCCCO yields a product that has a SMILES string of CCCCCC(=O)O.

A) An illustration shows a chemical reaction. The reactant has a five-carbon chain, in which C 1 is bonded to M g B r reacts in presence of formaldehyde, a central carbon atom single bonded to two hydrogen atoms and double bonded to an oxygen atom in the first step, and water molecule, H 2 O in the second step to yield a product. The product has a SMILES string of CCCCCCO.

B) In reaction B, the reactant has a five-carbon chain, in which C 1 is bonded to M g that reacts in presence of B r 2 to yield a product. The product has a five-carbon chain, in which C 1 is bonded to M g B r.

D) In reaction D, the reactant that has a SMILES string of CCCCCO reacts with phosphorus tribromide, P B r 3, to yield an intermediate that has a SMILES string of CCCCCBr. In the second step, the intermediate reacts with magnesium, M g, and ether.

Diff: 3

Learning Objective: 12.13 List the two key issues to consider when proposing a synthesis

146) Which one of the following compounds is consistent with the IR spectrum shown?

SDBS: National Institute of Advanced Industrial Science and Technology

An illustration shows four compounds represented by their bond-line structure. The first compound has a SMILES string of CC(CCC#C)O. The second compound has a SMILES string of CC(CCC(=O)O)O. The third compound has a SMILES string of CC=CCCC(C)O. The fourth compound has a SMILES string of CCCC(=O)O.

A) I

B) II

C) III

D) IV

Diff: 2

Learning Objective: Spectroscopy

147) Which one of the compounds shown is consistent with the given IR spectrum?

SDBS: National Institute of Advanced Industrial Science and Technology

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of CCCC(C)O. The second compound has a SMILES string of CCCC(=O)O. The third compound has a SMILES string of c1ccc(cc1)O. The fourth compound has a SMILES string of C/C=C/C(=O)O. The fifth compound has a SMILES string of C/C=C/C(C)O.

A) I

B) II

C) III

D) IV

E) V

Diff: 2

Learning Objective: Spectroscopy

148) Which of the compounds shown is consistent with the given proton decoupled 13C NMR spectrum?

An illustration shows four compounds represented by their bond-line structure. The first compound has a SMILES string of CCCC(C)O. The second compound has a SMILES string of CC(C)(C)CO. The third compound has a SMILES string of CC(C)C(C)O. The fourth compound has a SMILES string of CCC(C)(C)O.

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: Spectroscopy

149) Which of the compounds shown is consistent with the given proton decoupled 13C NMR spectrum?

A) I

B) II

C) III

D) IV

E) none of these

Diff: 3

Learning Objective: Spectroscopy

150) A compound with a molecular formula C9H12O has the 1H NMR spectrum shown. Which of the following structures is consistent with this spectrum?

An illustration shows five compounds represented by their bond-line structure. The first compound has a SMILES string of COCc1ccc(cc1)I. The second compound has a SMILES string of CCc1ccc(cc1)CO. The third compound has a SMILES string of CCCc1ccc(cc1)O. The fourth compound has a SMILES string of CCc1cccc(c1)CO. The fifth compound has a SMILES string of c1ccc(cc1)CCCO.

A) I

B) II

C) III

D) IV

E) V

Diff: 3

Learning Objective: Spectroscopy

151) A compound with a molecular formula C6H14O exhibits the 1H NMR and 13C NMR spectra. Propose a structure for this compound.

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

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

An illustration shows the bond-line structure of a compound. The compound has a SMILES string of CCCCCO.

An illustration shows the bond-line structure of a compound. The compound has a SMILES string of CCCCC(C)O.

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

Diff: 3

Learning Objective: Spectroscopy

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Chapter 12 Alcohols And Phenols

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David R. Klein

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