The combination of ester and Grignard reagent required for the formation of given tertiary alcohols is to be identified. Concept Introduction: The reaction between esters and Grignard reagent results in the formation of tertiary alcohols. In the first step of this reaction, nucleophilic attack of Grignard reagent takes place on the carbonyl carbon of ester and forms an intermediate. In the next step, removal of leaving group takes place from the intermediate which results in the formation of a ketone . Then, neuclophilic attack of Grignard reagent takes place on the carbonyl carbon of ketone followed by acidic hydrolysis which results in the formation of tertiary alcohol.

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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 20.11, Problem 15P

Interpretation Introduction

Interpretation:

The combination of ester and Grignard reagent required for the formation of given tertiary alcohols is to be identified.

Concept Introduction:

The reaction between esters and Grignard reagent results in the formation of tertiary alcohols.

In the first step of this reaction, nucleophilic attack of Grignard reagent takes place on the carbonyl carbon of ester and forms an intermediate.

In the next step, removal of leaving group takes place from the intermediate which results in the formation of a ketone.

Then, neuclophilic attack of Grignard reagent takes place on the carbonyl carbon of ketone followed by acidic hydrolysis which results in the formation of tertiary alcohol.

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Problem 19.22 Show how ethyl bromide can be used as a starting material in the preparation of each of the following compounds. (Hint: How are Grignard reagents prepared?) HO `CH;CH3 (a) OH (b) OH (c) 1-butanol (d) PHCHCH,CH; (CH;CH;),CCH3

MeO 22.55 One potential synthesis of the anti-inflammatory and analgesic drug nabumetone is chloromethylation (Problem 22.48) of 2-methoxynaphthalene followed by an acetoacetic ester synthesis (Section 19.6). 5 3 6 CH₂O CI acetoacetic ester synthesis HC 7 MeO MeO 1 8 2-Methoxynaphthalene Nabumetone (a) Account for the regioselectivity of chloromethylation at carbon 6 rather than at carbon 5 or 7. (b) Show steps in the acetoacetic ester synthesis by which the synthesis of nabum- etone is completed.

provide the missing reagents as appropriate

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 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 20.11, Problem 15P

Interpretation Introduction

Interpretation:

The combination of ester and Grignard reagent required for the formation of given tertiary alcohols is to be identified.

Concept Introduction:

The reaction between esters and Grignard reagent results in the formation of tertiary alcohols.

In the first step of this reaction, nucleophilic attack of Grignard reagent takes place on the carbonyl carbon of ester and forms an intermediate.

In the next step, removal of leaving group takes place from the intermediate which results in the formation of a ketone.

Then, neuclophilic attack of Grignard reagent takes place on the carbonyl carbon of ketone followed by acidic hydrolysis which results in the formation of tertiary alcohol.

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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 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 20.11, Problem 15P

Interpretation Introduction

Interpretation:

The combination of ester and Grignard reagent required for the formation of given tertiary alcohols is to be identified.

Concept Introduction:

The reaction between esters and Grignard reagent results in the formation of tertiary alcohols.

In the first step of this reaction, nucleophilic attack of Grignard reagent takes place on the carbonyl carbon of ester and forms an intermediate.

In the next step, removal of leaving group takes place from the intermediate which results in the formation of a ketone.

Then, neuclophilic attack of Grignard reagent takes place on the carbonyl carbon of ketone followed by acidic hydrolysis which results in the formation of tertiary alcohol.

Expert Solution & Answer

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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 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 20.11, Problem 15P

Interpretation Introduction