The stereoisomers formed from the cyclization of both A and B , are to be drawn, and an explanation for an optically inactive product mixture from A and an optically active product mixture from B is to be stated. Concept introduction: The formation of a cyclic hemiacetal is an acid catalyzed reaction. The cyclic hemiacetals formed by the intramolecular cyclization of hydroxyl aldehydes . This process leads to the formation of equal amount of hemiacetal enantiomers with a new stereogenic center.

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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 21, Problem 21.49P

Interpretation Introduction

Interpretation: The stereoisomers formed from the cyclization of both A and B, are to be drawn, and an explanation for an optically inactive product mixture from A and an optically active product mixture from B is to be stated.

Concept introduction: The formation of a cyclic hemiacetal is an acid catalyzed reaction. The cyclic hemiacetals formed by the intramolecular cyclization of hydroxyl aldehydes. This process leads to the formation of equal amount of hemiacetal enantiomers with a new stereogenic center.

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5) Draw the enols available to compounds A-D. Explain why A is 100% enolized but B, C, and D are 100% ketone. B D

Hydroxy aldehydes A and B readily cyclize to form hemiacetals. Draw the stereoisomers formed in this reaction from both A and B. Explain why this process gives an optically inactive product mixture from A, and an optically active product mixture from B. CHO CHO но A B

(c) Draw the structure of the hemi-acetal and acetal formed when cyclohexanone is combined with methanol in the presence of catalytic acid.

Answer 2

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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 21, Problem 21.49P

Interpretation Introduction

Interpretation: The stereoisomers formed from the cyclization of both A and B, are to be drawn, and an explanation for an optically inactive product mixture from A and an optically active product mixture from B is to be stated.

Concept introduction: The formation of a cyclic hemiacetal is an acid catalyzed reaction. The cyclic hemiacetals formed by the intramolecular cyclization of hydroxyl aldehydes. This process leads to the formation of equal amount of hemiacetal enantiomers with a new stereogenic center.

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Answer 3

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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 21, Problem 21.49P

Interpretation Introduction

Interpretation: The stereoisomers formed from the cyclization of both A and B, are to be drawn, and an explanation for an optically inactive product mixture from A and an optically active product mixture from B is to be stated.

Concept introduction: The formation of a cyclic hemiacetal is an acid catalyzed reaction. The cyclic hemiacetals formed by the intramolecular cyclization of hydroxyl aldehydes. This process leads to the formation of equal amount of hemiacetal enantiomers with a new stereogenic center.

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Check out a sample textbook solution

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Answer 4

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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 21, Problem 21.49P

Interpretation Introduction