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

In the analysis of Mg content in a 25 mL sample, a titration volume of 5 mL was obtained using 0.01 M EDTA. Calculate the Mg content in the sample if the Ca content is 20 ppm

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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In the analysis of Mg content in a 25 mL sample, a titration volume of 5 mL was obtained using 0.01 M EDTA. Calculate the Mg content in the sample if the Ca content is 20 ppm

Predict the organic products that form in the reaction below: H. H+ + OH H+ Y Note: You may assume you have an excess of either reactant if the reaction requires more than one of those molecules to form the products. In the drawing area below, draw the skeletal ("line") structures of the missing organic products X and Y. You may draw the structures in any arrangement that you like, so long as they aren't touching. Explanation Check Click and drag to start drawing a structure. G X C © 2025 McGraw Hill LLC. All Rights Reserved. Terms of Use | Privacy Center | Access +

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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.