a) Interpretation: All possible compounds which give benzyl alcohol on reduction with LiAlH 4 are to be given. Concept introduction: All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH 4 . Acids, esters and aldehydes yield a 1 0 alcohol upon reduction with LiAlH 4 , while ketones yield 2 0 alcohols. The reaction is carried out in ether solution as LiAlH 4 reacts violently with water and explodes when heated above 120 o C. To give: All possible compounds which give benzyl alcohol on reduction with LiAlH 4 .

Question

21.50 Determine the combinations of haloalkane(s) and alkoxide(s) that could be used to synthesize the following ethers through Williamson ether synthesis. (a) (c) (d) (e) (f) H₂CO

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

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21.50 Determine the combinations of haloalkane(s) and alkoxide(s) that could be used to synthesize the following ethers through Williamson ether synthesis. (a) (c) (d) (e) (f) H₂CO

1. Arrange the following in order of increasing bond energy (lowest bond energy first, highest bond energy last). Provide your rationale. C=C, C-F, C=C, C-N, C-C List the bond order for each example.

What is the major enolate formed when treated with LDA? And why that one?

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

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Answer 5

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

Answer 6

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Answer 7

Chapter 17.4, Problem 8P

Interpretation Introduction

a)

Interpretation:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give benzyl alcohol on reduction with LiAlH₄.

Answer 8

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Answer 9

Interpretation Introduction

b)

Interpretation:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give 1-phenylethanol on reduction with LiAlH₄.

Answer 10

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Answer 11

Interpretation Introduction

c)

Interpretation:

All possible compounds which give cyclohexanol on reduction with LiAlH₄ are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 1⁰ alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give cyclohexanol on reduction with LiAlH₄.

Answer 12

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

Answer 13

Interpretation Introduction

d)

Interpretation:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4 are to be given.

Concept introduction:

All carbonyl compounds, including acids, esters, aldehydes and ketones are reduced by LiAlH₄. Acids, esters and aldehydes yield a 10 alcohol upon reduction with LiAlH₄, while ketones yield 2⁰ alcohols. The reaction is carried out in ether solution as LiAlH₄ reacts violently with water and explodes when heated above 120^oC.

To give:

All possible compounds which give isobutyl alcohol on reduction with LiAlH4.

Answer 14

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Answer 15

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Answer 25

Ch. 17.1 - Give IUPAC names for the following compounds:Ch. 17.1 - Prob. 2P Ch. 17.2 - The following data for isomeric four-carbon...Ch. 17.2 - Rank the following substances in order of...Ch. 17.2 - Prob. 5P Ch. 17.3 - Prob. 6P Ch. 17.4 - What reagent would you use to accomplish each of...Ch. 17.4 - Prob. 8P Ch. 17.5 - Prob. 9P Ch. 17.5 - Prob. 10P

Solution Summary: The author explains that benzyl alcohol can be prepared by reducing Benzaldehyde or benzoic acid or a Benzoyate Ester with LiAlH 4 followed by acidification.

Concept explainers

Chapter 17 Solutions