The observation, when the unsymmetrical ketone , 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained. Concept introduction: The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable. To explain: The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

Question

When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Why doesn’t the cis isomer yield the oxide?

Answer 1

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained.

Concept introduction:

The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable.

To explain:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

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When trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone. Why doesn’t the cis isomer yield the oxide?

Hydration of aldehydes and ketones can be catalyzed by acid or base. Bases catalyze hydration by: protonating the carbonyl oxygen making the carbonyl group more electrophilic employing hydroxide ion, which is a better nucleophile than water making the carbonyl group less electrophilic shifting the equilibrium position of the reaction to favor products

Draw the structure of the major organic product(s) for the following reaction between an acetylenic anion and an alkyl halide. (The reaction stoichiometry is 1:1.)

Answer 2

Question

Definition Definition Organic compounds that have a carbonyl group, C = O, as their functional group. The carbonyl group in ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained.

Concept introduction:

The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable.

To explain:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

Expert Solution & Answer

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 73AP

Interpretation Introduction

Interpretation:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed, is to be explained.

Concept introduction:

The enamine obtained from an unsymmetrical ketone will be stable only if it is free from steric strain. A strained unsymmetrical ketone will be unstable.

To explain:

The observation, when the unsymmetrical ketone, 2-methylcyclohexenone is converted into an enamine the sole product is the one with the double bond opposite to the methyl substituted carbon while the other possible enamine with methyl on the carbon in double bond is not formed.

Expert Solution & Answer

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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 ketones is placed somewhere in the middle of the molecular structure, which means, the C=O is attached to two alkyl groups or benzene rings. Just like all other homologous series, the naming of ketones is done using a common suffix “-one”. The general molecular formula is C n H 2n O. Functional group of a ketone

Chapter 23.SE, Problem 73AP

Interpretation Introduction