Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given. Concept Introduction: Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid. Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows, Step 1: Add proton (protonation of Pinacol using acid catalyst). Step 2: Break a bond to give a stable molecules or ions (formation of carbocation). Step 3: 1, 2-shift (migration of substituent from α- to β- carbon). Step 4: deprotonation occurs (take a proton away).

Question

Briefly explain why, under aqueous acidic conditions, furan readily undergoes a reversible ring opening reaction to give succinaldehyde.

Answer 1

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

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Briefly explain why, under aqueous acidic conditions, furan readily undergoes a reversible ring opening reaction to give succinaldehyde.

The ketone shown was prepared in a three-step sequence from ethyl trifluoroacetate. The first step in the sequence involved treating ethyl trifluoroacetate with ammonia to give compound A. Compound A was in turn converted to the desired ketone by way of compound B. Fill in the missing reagents in the sequence shown, and give the structures of compounds A and B.

(a) State and illustrate the following :(i) Wolff-Kishner reduction (ii) Aldol condensation(b) An organic compound (A) which has characteristic odour, on treatment with NaOH forms two compounds (B) and (C). Compound (B) has the molecular formula C7H8O which on oxidation with CrO3 gives back compound (A). Compound (C) is the sodium salt of the acid. Compound (C) when heated with soda lime yields an aromatic hydrocarbon (D). Deduce the structures of (A), (B), (C) and (D). Write chemical equations for all reactions taking place.

Answer 2

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Expert Solution & Answer

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Answer 3

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Expert Solution & Answer

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Answer 4

Question

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Expert Solution & Answer

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Answer 5

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Answer 6

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 7

Chapter 23, Problem 23.37P

(a)

Interpretation Introduction

Interpretation:

Similarities between the mechanism of deamination of β- aminoalcohol using nitrous acid and Pinacol rearrangement has to be given.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 8

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 9

(b)

Interpretation Introduction

Interpretation:

Reason for the expansion of ring in the deamination of β- aminoalcohol using nitrous acid not in Pinacol rearrangement has to be explained.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Pinacol rearrangement: For all glycols Pinacol rearrangement occurs. Unsymmetrical vicinal diols reveal that –OH group that becomes protonated and leaves in the one that gives rise to more stable carbocation. Acid-catalyzed conversion of Pinacol to pinacolone followed by four step mechanism as follows,

Step 1: Add proton (protonation of Pinacol using acid catalyst).

Step 2: Break a bond to give a stable molecules or ions (formation of carbocation).

Step 3: 1, 2-shift (migration of substituent from α- to β- carbon).

Step 4: deprotonation occurs (take a proton away).

Answer 10

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Answer 11

(b)

Interpretation Introduction

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Answer 12

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Answer 23

Ch. 23.1 - Prob. 23.1P Ch. 23.2 - Prob. 23.2P Ch. 23.2 - Prob. 23.3P Ch. 23.2 - Prob. 23.4P Ch. 23.5 - Prob. 23.5P Ch. 23.5 - Prob. AQ Ch. 23.5 - What is the hybridization of the nitrogen in...Ch. 23.5 - Prob. CQ Ch. 23.5 - The pKas of the conjugate acids of aniline and...Ch. 23.5 - Prob. EQ

Interpretation: β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested. Concept Introduction: Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.

Chapter 23 Solutions

Interpretation:

β- Aminoalcohol that gives cyclohexanecarbaldehyde has to be suggested.

Concept Introduction:

Tiffeneau–Demjanov reaction: It is an organic reaction where 1-aminomethyl-cycloalkanol gets converted to an enlarged cycloketone by reacting with nitrous acid.