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

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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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Please help me with # 4 and 5. Thanks in advance!

A small artisanal cheesemaker is testing the acidity of their milk before it coagulates. During fermentation, bacteria produce lactic acid (K₁ = 1.4 x 104), a weak acid that helps to curdle the milk and develop flavor. The cheesemaker has measured that the developing mixture contains lactic acid at an initial concentration of 0.025 M. Your task is to calculate the pH of this mixture and determine whether it meets the required acidity for proper cheese development. To achieve the best flavor, texture and reduce/control microbial growth, the pH range needs to be between pH 4.6 and 5.0. Assumptions: Lactic acid is a monoprotic acid H H :0:0: H-C-C H :0: O-H Figure 1: Lewis Structure for Lactic Acid For simplicity, you can use the generic formula HA to represent the acid You can assume lactic acid dissociation is in water as milk is mostly water. Temperature is 25°C 1. Write the K, expression for the dissociation of lactic acid in the space provided. Do not forget to include state symbols.…

Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. :0: :0 H. 0:0 :0: :6: S: :0: Select to Edit Arrows ::0 Select to Edit Arrows H :0: H :CI: Rotation Select to Edit Arrows H. < :0: :0: :0: S:

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 - 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