Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)- 3 -methylpentan- 2 -one is to be shown. Concept introduction: In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

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Answer 1

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

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Answer 2

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Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

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Answer 3

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

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Answer 4

Question

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

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Answer 5

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

Answer 6

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

Answer 7

Chapter 22.2A, Problem 22.2P

(a)

Interpretation Introduction

Interpretation:

Each step in the mechanism of the acid-catalysed interconversion of (R)-and (S)-3-methylpentan-2-one is to be shown.

Concept introduction:

In acid catalysed keto-enol tautomerism, the carbonyl oxygen is protonated by an acid. In the next step, deprotonation occurs at the alpha carbon to give the enol form. This is applicable on most of the proton-transfer mechanisms.

Answer 8

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

Answer 9

(b)

Interpretation Introduction

Interpretation:

A mechanism for the isomerization that occurs when cis-2,4-dimethylcyclohexanone is dissolved in aqueous ethanol containing a trace of NaOH is to be proposed.

Concept introduction:

In base catalysed keto-enol tautomerism, the proton is removed from the alpha carbon. In the next step, reprotonation occurs at oxygen to give a vinyl alcohol (enol form). Ketones and aldehydes act as weak proton acids in the presence of strong bases.

Answer 10

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Answer 12

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Answer 13

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 the mechanism of the acid-catalysed interconversion of (R)-and (S), which is applicable on most proton-transfer mechanisms.

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