(a) Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn. Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively. Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Question

(a) Draw two different halo ketones that can form A by an intramolecularalkylation reaction. (b) How can A be synthesized by an acetoacetic estersynthesis?

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 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

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(a) Draw two different halo ketones that can form A by an intramolecularalkylation reaction. (b) How can A be synthesized by an acetoacetic estersynthesis?

(c) Draw the structure of the hemi-acetal and acetal formed when cyclohexanone is combined with methanol in the presence of catalytic acid.

Tautomerization in base resembles tautomerization in acid, but deprotonation precedes protonation in the two-step mechanism. (a) Draw a stepwise mechanism for the following tautomerization. (b) Then draw a stepwise mechanism for the reverse reaction, the conversion of the keto form to the enol.

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 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

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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 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

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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 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

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Answer 5

Chapter 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Answer 6

Chapter 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Answer 7

Chapter 23, Problem 23.62P

Interpretation Introduction

(a)

Interpretation: Two different halo ketones that can form A by an intramolecular alkylation reaction is to be drawn.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Lithium diisopropylamide (LDA) is a sterically hindered strong base. In an unsymmetrical ketone, it abstracts hydrogen from least substituted carbon to form kinetic product.

Answer 8

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Answer 9

Interpretation Introduction

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Answer 10

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Answer 21

Ch. 23 - Problem 23.1 Draw the enol or keto tautomer(s) of...Ch. 23 - Prob. 23.2P Ch. 23 - Problem 23.3 When phenylacetaldehyde is dissolved...Ch. 23 - Prob. 23.4P Ch. 23 - Problem 23.5 Which bonds in the following...Ch. 23 - Prob. 23.6P Ch. 23 - Prob. 23.7P Ch. 23 - Prob. 23.8P Ch. 23 - Prob. 23.9P Ch. 23 - Prob. 23.10P

Solution Summary: The author explains that the synthesis of compound A from acetoacetic ester is to be devised.

Concept explainers

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Chapter 23 Solutions

Solution Summary: The author explains that the synthesis of compound A from acetoacetic ester is to be devised.

Concept explainers

(b) Interpretation: The synthesis of compound A from acetoacetic ester is to be devised. Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.

Chapter 23 Solutions

(b)

Interpretation: The synthesis of compound A from acetoacetic ester is to be devised.

Concept introduction: Alkylation of aldehydes and ketones takes place in the presence of a strong base. The use of appropriate base, solvent and temperature can yield one major product regioselectively.