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

Want to see the full answer?

Answer 1

Question

Chapter 22, Problem 75PP

(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

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

In the phase diagram of steel (two components Fe and C), region A is the gamma austenite solid and region B contains the gamma solid and liquid. Indicate the degrees of freedom that the fields A and B have,

For a condensed binary system in equilibrium at constant pressure, indicate the maximum number of phases that can exist.

Part V. Label ad match the carbons in compounds Jane and Diane w/ the corresponding peak no. in the Spectra (Note: use the given peak no. To label the carbons, other peak no are intentionally omitted) 7 4 2 -0.13 -0.12 -0.11 -0.10 -0.08 8 CI Jane 1 -0.09 5 210 200 190 180 170 160 150 140 130 120 110 100 -8 90 f1 (ppm) 11 8 172.4 172.0 f1 (ppr HO CI NH Diane 7 3 11 80 80 -80 -R 70 60 60 2 5 -8 50 40 8. 170 160 150 140 130 120 110 100 90 -0 80 70 20 f1 (ppm) 15 30 -20 20 -60 60 -0.07 -0.06 -0.05 -0.04 -0.03 -0.02 -0.01 -0.00 -0.01 10 -0.17 16 15 56 16 -0.16 -0.15 -0.14 -0.13 -0.12 -0.11 -0.10 -0.09 -0.08 -0.07 -0.06 -0.05 -0.04 17.8 17.6 17.4 17.2 17.0 f1 (ppm) -0.03 -0.02 550 106 40 30 20 20 -0.01 -0.00 F-0.01 10 0

Answer 2

Question

Chapter 22, Problem 75PP

(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

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 22, Problem 75PP

(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

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 22, Problem 75PP

(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

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 22, Problem 75PP

(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 22, Problem 75PP

(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 22, Problem 75PP

(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

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 15

Ch. 22.1 - Prob. 1CC Ch. 22.1 - Prob. 2CC Ch. 22.1 - Prob. 3CC Ch. 22.1 - Prob. 1LTS Ch. 22.1 - Prob. 4PTS Ch. 22.1 - Prob. 5ATS Ch. 22.1 - Prob. 6CC Ch. 22.1 - Prob. 7CC Ch. 22.1 - Prob. 8CC Ch. 22.2 - Prob. 9CC

Want to see the full answer?

Chapter 22 Solutions