A mechanism for the formation of a purple-colored compound from ninhydrin has to be proposed. Concept introduction: Ninhydrin reacts with amino acid to form a purple-colored compound. The reaction is thus used to identify amines. It is a test given by all amino acids. Ninhydrin acts as an oxidizing agent and the product formed is a reduced form of ninhydrin, carbon dioxide, and an aldehyde .

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Answer 1

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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 17, Problem 82P

Interpretation Introduction

Interpretation: A mechanism for the formation of a purple-colored compound from ninhydrin has to be proposed.

Concept introduction: Ninhydrin reacts with amino acid to form a purple-colored compound. The reaction is thus used to identify amines. It is a test given by all amino acids. Ninhydrin acts as an oxidizing agent and the product formed is a reduced form of ninhydrin, carbon dioxide, and an aldehyde.

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When an α-hydroxy amide is treated with Br2 in aqueous NaOH under Hofmann rearrangement conditions, loss of CO2 occurs and a chain-shortened aldehyde is formed. The mechanism involves the following steps: Base abstracts an acidic amide proton, yielding amide anion 1; The amide anion reacts with bromine in an α-substitution reaction to give N-bromoamide 2. Abstraction of the remaining amide proton by base gives a resonance-stabilized bromoamide anion 3; Rearrangement occurs to yield isocyanate 4; Water adds to the isocyanate to yield carbamic acid 5; Elimination of CO2 yields carbinolamine 6; Following proton transfer, expulsion of ammonia yields the final product aldehyde. Write out the mechanism and then draw the structures of bromoamide anion 3 and amide anion 1.

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 17, Problem 82P

Interpretation Introduction

Interpretation: A mechanism for the formation of a purple-colored compound from ninhydrin has to be proposed.

Concept introduction: Ninhydrin reacts with amino acid to form a purple-colored compound. The reaction is thus used to identify amines. It is a test given by all amino acids. Ninhydrin acts as an oxidizing agent and the product formed is a reduced form of ninhydrin, carbon dioxide, and an aldehyde.

Expert Solution & Answer

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Check out a sample textbook solution

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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 17, Problem 82P

Interpretation Introduction

Interpretation: A mechanism for the formation of a purple-colored compound from ninhydrin has to be proposed.

Concept introduction: Ninhydrin reacts with amino acid to form a purple-colored compound. The reaction is thus used to identify amines. It is a test given by all amino acids. Ninhydrin acts as an oxidizing agent and the product formed is a reduced form of ninhydrin, carbon dioxide, and an aldehyde.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See 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 17, Problem 82P

Interpretation Introduction