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? Write 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 23, Problem 23.17P

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? Write the structure of each intermediate. Explain why a racemic product is formed.

Why is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone? A) The Grignard reagent will react with the acid and cannot react with the ketone. B) The ketone will be protonated and will become unreactive. C) The ketone will form an unreactive enol. D) The Grignard reagent won't dissolve in aqueous solutions

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 23.17P

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 23, Problem 23.17P

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 23, Problem 23.17P

Interpretation Introduction