The mechanism for the given reaction is to be stated. Concept introduction: In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

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Answer 1

Question

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

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For the following reaction there are three (3) possible products. Two of the products are expected to be minor and one product is expected to be a major product. Br H₂O Name and draw out the step-by-step mechanisms by which each of the products is formed. Briefly explain why one of the three products is expected to be a major product.

The chlorination of ethane produces many by-products. One by-product that forms in small amounts is 2-chlorobutane. Suggest a mechanism for the formation of 2-chlorobutane from the radical chlorination of ethane. (NOTES: intermediates can only have one radical, 2-chlorobutane should be the product of your termination step, any intermediate radical formed during the propagation phase can be used in the termination step)

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Answer 2

Question

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

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Answer 3

Question

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

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Answer 4

Question

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

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Answer 5

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

Answer 6

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

Answer 7

Chapter 22, Problem 22.80SP

(a)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

Answer 8

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

Answer 9

(b)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In acid-catalysed Aldol condensation, nucleophilic addition of an enol takes place at a protonated carbonyl group. In the first step, enol is formed when carbonyl oxygen gets protonated. Then, deprotonation occurs at alpha carbon. In the next step, enol adds to the protonated carbonyl followed by deprotonation to give the aldol product.

Answer 10

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

Answer 11

(c)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

Answer 12

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

Answer 13

(d)

Interpretation Introduction

Interpretation:

The mechanism for the given reaction is to be stated.

Concept introduction:

In base-catalysed aldol condensation, nucleophilic addition of an enolate ion takes place on a carbonyl group. In first step, an alpha proton is removed to produce enolate ion. It adds to the carbonyl group. In the next step, protonation of alkoxide gives the aldol product.

Answer 14

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Answer 15

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Answer 16

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Answer 17

Ch. 22.2A - Prob. 22.2P Ch. 22.4 - Without looking back, propose a mechanism for the...Ch. 22.4 - Prob. 22.8P Ch. 22.4 - Prob. 22.9P Ch. 22.5A - Prob. 22.10P Ch. 22.5A - Prob. 22.11P Ch. 22.5B - Prob. 22.12P Ch. 22.5B - Predict the products of the following reactions....Ch. 22.5B - Which compounds will give positive iodoform tests?...Ch. 22.5C - Propose a mechanism for the acid-catalyzed...

Solution Summary: The author explains how nucleophilic addition of an enol takes place at a protonated carbonyl group. The mechanism for the given reaction is shown in Figure 1.

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Chapter 22 Solutions