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.

Question

Which of the following is the product in this Grignard reaction? ОН O 1) O 2) ОН 4) H.

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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Which of the following is the product in this Grignard reaction? ОН O 1) O 2) ОН 4) H.

The base-promoted rearrangement of an a-haloketone to a carboxylic acid, known as the Favorskii rearrangement, is illustrated by the conversion of 2-chlorocyclohexanone to cyclopentanecarboxylic acid. Jo Han Sow La NaOH, THF O Nat H3O+ OH NaOH, THF The mechanism involves the following 5 steps: -ō cyclopropanone intermediate 1. Abstraction of a proton to form enolate anion 1; 2. Formation of a cyclopropanone intermediate 2 with expulsion of chloride ion; 3. Addition of hydroxide ion to form tetrahedral intermediate 3; 4. Collapse of the tetrahedral intermediate and breakage of the three-membered ring to form carbanion intermediate 4; 5. Proton transfer to form the rearranged carboxylic acid. For the following reaction, draw the reaction out on paper, and then draw the structure of cyclopropanone intermediate 2 in the window. 1. NaOH, THF 2. H3O* OH

OH oth -H H H3C- NX XT OAc ACO -OAc & O Dess-Martin periodinane provides a means to oxidize a primary alcohol to an aldehyde, while avoiding the use of toxic Cr(VI) compounds. The mechanism involves a reaction similar to the E2 elimination, whereby a C=O double bond is formed with a reduced iodine compound as the leaving group. The reaction occurs in a nonaqueous solvent, CH₂Cl₂, so that the aldehyde product can be recovered. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H3C CH3 H ACO $$ H H3C H3C H :0: H H3C OH OAC чь

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.

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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 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 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