Peptides may be synthesized using an α-keto acid and a hydroxylamine. Concept introduction: The reaction of formation of an amide/ peptide from an α-keto acid and a hydroxylamine involves an initial nucleophilic substitution of the alkyl group to the keto group followed by decarboxylation and elimination of water molecule. To determine: Mechanism of reaction thought to occur by nucleophilic addition of the N-alkylhydroxylamine to the keto acid as if forming an oxime.

Question

Predict the organic products that form in the reaction below, and draw the skeletal ("line") structures of the missing organic products. Please include all steps & drawings & explanations.

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 26.SE, Problem 28MP

Interpretation Introduction

Interpretation:

Peptides may be synthesized using an α-keto acid and a hydroxylamine.

Concept introduction:

The reaction of formation of an amide/ peptide from an α-keto acid and a hydroxylamine involves an initial nucleophilic substitution of the alkyl group to the keto group followed by decarboxylation and elimination of water molecule.

To determine:

Mechanism of reaction thought to occur by nucleophilic addition of the N-alkylhydroxylamine to the keto acid as if forming an oxime.

Expert Solution & Answer

Trending nowThis is a popular solution!

See solution

Check out sample textbook solution

Students have asked these similar questions

Predict the organic products that form in the reaction below, and draw the skeletal ("line") structures of the missing organic products. Please include all steps & drawings & explanations.

What are the missing reagents for the spots labeled 1 and 3? Please give a detailed explanation and include the drawings and show how the synthesis proceeds with the reagents.

What are the products of the following acetal hydrolysis? Please draw a skeletal line structure and include a detailed explanation and drawing of how the mechanism proceeds. Please include any relevant information that is needed to understand the process of acetal hydrolysis.

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 26.SE, Problem 28MP

Interpretation Introduction

Interpretation:

Peptides may be synthesized using an α-keto acid and a hydroxylamine.

Concept introduction:

The reaction of formation of an amide/ peptide from an α-keto acid and a hydroxylamine involves an initial nucleophilic substitution of the alkyl group to the keto group followed by decarboxylation and elimination of water molecule.

To determine:

Mechanism of reaction thought to occur by nucleophilic addition of the N-alkylhydroxylamine to the keto acid as if forming an oxime.

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 26.SE, Problem 28MP

Interpretation Introduction

Interpretation:

Peptides may be synthesized using an α-keto acid and a hydroxylamine.

Concept introduction:

The reaction of formation of an amide/ peptide from an α-keto acid and a hydroxylamine involves an initial nucleophilic substitution of the alkyl group to the keto group followed by decarboxylation and elimination of water molecule.

To determine:

Mechanism of reaction thought to occur by nucleophilic addition of the N-alkylhydroxylamine to the keto acid as if forming an oxime.

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 26.SE, Problem 28MP

Interpretation Introduction