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

Indicate the compound that gives us a primary carbocation and that gives us a secondary carbocation: R-CHO and R-CO-R

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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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.

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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.

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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.

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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.