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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Predict the major products of this organic reaction: H OH 1. LiAlH4 2. H₂O ? Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry. Click and drag to start drawing a structure. G C टे

For each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. NH2 CI MgCl ? Will the first product that forms in this reaction create a new CC bond? Yes No MgBr ? Will the first product that forms in this reaction create a new CC bond? Yes No G टे

For each reaction below, decide if the first stable organic product that forms in solution will create a new CC bond, and check the appropriate box. Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below. Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first stable product you expect to form in solution. དྲ。 ✗MgBr ? O CI Will the first product that forms in this reaction create a new C-C bond? Yes No • ? Will the first product that forms in this reaction create a new CC bond? Yes No × : ☐ X

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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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 - Prob. 5ATS Ch. 21.1 - Prob. 6CC Ch. 21.1 - Prob. 7CC Ch. 21.2 - Prob. 8CC Ch. 21.2 - Prob. 9CC

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Chapter 21 Solutions