The observation, Grignard reaction of cyclohexanone with tert -butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D 3 O + is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained. Concept introduction: Grignard reagents add to the carbonyl group in aldehydes and ketones . The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones. Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers. To explain: The observation, Grignard reaction of cyclohexanone with tert -butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D 3 O + is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

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Reaction Fill-ins Part 2! Predict the product(s) OR starting material of the following reactions. Remember, Hydride shifts are possible if/when a more stable carbocation can exist (depending on reaction mechanism)! Put your answers in the indicated boxes d. d. ง HCI

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 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

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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 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

Expert Solution & Answer

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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 22.SE, Problem 61AP

Interpretation Introduction

Interpretation:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it, is to be explained.

Concept introduction:

Grignard reagents add to the carbonyl group in aldehydes and ketones. The addition product when hydrolyzed with aqueous acids yields a secondary alcohol in the case of aldehydes other than formaldehyde and a secondary alcohol in the case of ketones.

Ketones exist in acid catalyzed reversible equilibrium with their enol tatomers.

To explain:

The observation, Grignard reaction of cyclohexanone with tert-butylmagnesium bromide yields only about 1% of the expected addition product along with 99% unreacted cyclohexanone. If D₃O⁺ is added to the reaction mixture after a suitable period, however, the unreacted cyclohexanone is found to have one deuterium atom incorporated into it.

Expert Solution & Answer

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See solution

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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 22.SE, Problem 61AP

Interpretation Introduction