A synthesis of nifedipine from 2-nitrobenzaldehyde, methyl acetoacetate and ammonia has to be given. Concept introduction: Aldol condensation: Aldol reaction is an addition reaction of aldehydes and ketones . Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β -hydroxy aldehyde if two aldehydes combine and β -hydroxy ketone if two ketones combine. Michael reaction: The reaction occurs with a variety of α,β -unsaturated carbonyl compounds such as aldehydes, esters, nitriles, nitro compounds and amides. The donor compound of this reaction includes β -diketones, β -keto nitriles, β -keto esters.

Question

The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.

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 19, Problem 19.55P

Interpretation Introduction

Interpretation:

A synthesis of nifedipine from 2-nitrobenzaldehyde, methyl acetoacetate and ammonia has to be given.

Concept introduction:

Aldol condensation:

Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

Michael reaction:

The reaction occurs with a variety of α,β-unsaturated carbonyl compounds such as aldehydes, esters, nitriles, nitro compounds and amides.

The donor compound of this reaction includes β-diketones, β-keto nitriles, β-keto esters.

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The following substances can be prepared by a nucleophilic addition reaction between an aldehyde or ketoneand a nucleophile. Identify the reactants from which they were prepared. If the substance is an acetal, identifythe carbonyl compound and the alcohol; if it is an imine or enamine, identify the carbonyl compound and theamine. You do not have to consider stereochemistry. In cases where there is more than one answer, just giveone. Use Grignard reagents when an organometallic reagent is required. Draw the Grignard reagent as acovalent magnesium bromide.

In preparation of dibenzalacetone from benzaldehyde: Give two techniques that can be used to purify partially air-oxidized benzaldehyde. Indicate how each technique works in purifying benzaldebyde from its air-oxidized impurities.

this drug contains one or more building blocks derived from either ethylene oxide or epichlorohydrin.Identify the part of each molecule that can be derived from one or the other of the building block and propose structural formulas for the nucleophile(s) that can be used along with either ethylene oxide or epichlorohydrin to synthesize each molecule.

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 19, Problem 19.55P

Interpretation Introduction

Interpretation:

A synthesis of nifedipine from 2-nitrobenzaldehyde, methyl acetoacetate and ammonia has to be given.

Concept introduction:

Aldol condensation:

Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

Michael reaction:

The reaction occurs with a variety of α,β-unsaturated carbonyl compounds such as aldehydes, esters, nitriles, nitro compounds and amides.

The donor compound of this reaction includes β-diketones, β-keto nitriles, β-keto esters.

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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 19, Problem 19.55P

Interpretation Introduction

Interpretation:

A synthesis of nifedipine from 2-nitrobenzaldehyde, methyl acetoacetate and ammonia has to be given.

Concept introduction:

Aldol condensation:

Aldol reaction is an addition reaction of aldehydes and ketones. Aldol reaction is a reversible reaction and occurs in the presence of a strong base like sodium hydroxide. One molecule (aldehyde or ketone) acts a nucleophile and attacks the electrophilic carbon center of the other molecule to give the addition product. The product is named β-hydroxy aldehyde if two aldehydes combine and β-hydroxy ketone if two ketones combine.

Michael reaction:

The reaction occurs with a variety of α,β-unsaturated carbonyl compounds such as aldehydes, esters, nitriles, nitro compounds and amides.

The donor compound of this reaction includes β-diketones, β-keto nitriles, β-keto esters.

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 19, Problem 19.55P

Interpretation Introduction