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.

Question

Want to see the full answer?

Answer 1

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

Students have asked these similar questions

Show each step in the mechanism of the acid-catalyzed interconversion of (R)- and(S)-3-methylpentan-2-one.

Choose the best reagents from the list provided below for carrying out the following conversion. Match the reagent with the step number. HCl (aq), Zn(Hg) KMnO4, H3O+ CH3Cl, AlCl3 HNO3, H2SO4 Cl2, FeCl3 fuming sulfuric acid

1.Show the Elimination reaction of 2-bromopentane. 2.What contributed to formation of minor and major product?

Answer 2

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Expert Solution & Answer

Want to see the full answer?

Check out a sample textbook solution

See solution

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

Expert Solution & Answer

Answer 11

Expert Solution & Answer

Answer 12

Want to see the full answer?

Check out a sample textbook solution

See solution

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.

Concept explainers

Want to see the full answer?

Chapter 22 Solutions