Reagents needed to convert A to naproxen using enolate alkylation are to be predicted. The reason for the formation of a racemic product is to be stated. 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.

Question

The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.

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 21.8, Problem 18P

Interpretation Introduction

Interpretation: Reagents needed to convert A to naproxen using enolate alkylation are to be predicted. The reason for the formation of a racemic product is to be stated.

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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The analgesic naproxen can be prepared by a stepwise reaction sequence from ester A. Using enolate alkylation in one step, what reagents are needed to convert A to naproxen? Draw the structure of each intermediate. Explain why a racemic product is formed.

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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 21.8, Problem 18P

Interpretation Introduction

Interpretation: Reagents needed to convert A to naproxen using enolate alkylation are to be predicted. The reason for the formation of a racemic product is to be stated.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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 21.8, Problem 18P

Interpretation Introduction

Interpretation: Reagents needed to convert A to naproxen using enolate alkylation are to be predicted. The reason for the formation of a racemic product is to be stated.

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.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

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 21.8, Problem 18P

Interpretation Introduction