Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified. Concept introduction: Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic. To Find : To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

Question

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Answer 1

Question

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

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What would be the best choices for the missing reagents 1 and 3 in this synthesis? 1. PPh3 3 2. n-BuLi • Draw the missing reagents in the drawing area below. You can draw them in any arrangement you like. • Do not draw the missing reagent 2. If you draw 1 correctly, we'll know what it is. • Note: if one of your reagents needs to contain a halogen, use bromine. Click and drag to start drawing a structure.

Answer 2

Question

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

Expert Solution & Answer

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See solution

Answer 3

Question

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

Expert Solution & Answer

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Check out a sample textbook solution

See solution

Answer 5

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

Answer 6

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

Answer 7

Chapter 21, Problem 65PP

(a)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Find: To find the product formed when diethyl malonate undergoes bromination in acid catalyzed condition

Answer 8

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

Answer 9

(b)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To propose : To propose the mechanism for the above reaction

Answer 10

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

Answer 11

(c)

Interpretation Introduction

Interpretation:

Diethyl malonate reacts with bromine in acid catalyzed condition and the acidity of the product, structure of the product should be identified.

Concept introduction:

Under acid catalyzed conditions the carbonyl group gets protonated and gives a resonance stabilized intermediate resulting in formation of enol by deprotonation. The enol acts as a nucleophile and undergoes bromination to give an α -bromoketone or α -bromoaldehyde (acid-catalyzed halogenation) which then deprotonation in presence of water acting as base to form the final product. Inductive effect of the substituted halide stabilizes the formed conjugate base which inturn makes the compound more acidic.

To Predict: Whether product will be more acidic than starting material or not

Answer 12

Expert Solution & Answer

Answer 13

Expert Solution & Answer

Answer 14

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Answer 15

Ch. 21.1 - Prob. 1CC Ch. 21.1 - Prob. 2CC Ch. 21.1 - Prob. 3CC Ch. 21.1 - Prob. 1LTS Ch. 21.1 - Prob. 4PTS Ch. 21.1 - APPLY the skill As with aldehydes and ketones, the...Ch. 21.1 - Draw the enolate ion that is formed when each of...Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions