To predict the major product and propose a mechanism for the given set of reactions. Concept introduction: Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide . If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated. Deprotonation of α carbon to form enolate Alkylation with alkyl halide To predict : The predict the major product and propose a mechanism

Question

Want to see the full answer?

Answer 1

Question

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

3. Propose a synthesis for the following transformation. Do not draw an arrow-pushing mechanism below, but make sure to draw the product of each proposed step (3 points). CN + En CN

3) Propagation of uncertainty. Every measurement has uncertainty. In this problem, we'll evaluate the uncertainty in every step of a titration of potassium hydrogen phthalate (a common acid used in titrations, abbreviated KHP, formula CsH5KO4) with NaOH of an unknown concentration. The calculation that ultimately needs to be carried out is: concentration NaOH 1000 x mass KHP × purity KHP molar mass KHP x volume NaOH Measurements: a) You use a balance to weigh 0.3992 g of KHP. The uncertainty is ±0.15 mg (0.00015 g). b) You use a buret to slowly add NaOH to the KHP until it reaches the endpoint. It takes 18.73 mL of NaOH. The uncertainty of the burst is 0.03 mL.. c) The manufacturer states the purity of KHP is 100%±0.05%. d) Even though we don't think much about them, molar masses have uncertainty as well. The uncertainty comes from the distribution of isotopes, rather than random measurement error. The uncertainty in the elements composing KHP are: a. Carbon: b. Hydrogen: ±0.0008…

Don't used hand raiting and don't used Ai solution

Answer 2

Question

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 3

Question

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 4

Question

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Answer 5

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Answer 6

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Answer 7

Chapter 21.5, Problem 29CC

(a)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Answer 8

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Answer 9

(b)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Answer 10

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

Answer 11

(c)

Interpretation Introduction

Interpretation:

To predict the major product and propose a mechanism for the given set of reactions.

Concept introduction:

Ketone when treated with a base undergoes deprotonation at the α carbon to form enolate. The enolate formed undergoes alkylation when treated with alkyl halide. If LDA is used as a base the less substituted α carbon is deprotonated due to steric hindrance but if NaH is used as base means the more substituted α carbon is deprotonated.

Deprotonation of α carbon to form enolate

Alkylation with alkyl halide

To predict : The predict the major product and propose a mechanism

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. 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

Want to see the full answer?

Chapter 21 Solutions