Organic Chemistry
Organic Chemistry
2nd Edition
ISBN: 9781118452288
Author: David R. Klein
Publisher: WILEY
Question
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Chapter 13, Problem 35PP

(a)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

 (b)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(c)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

 (d)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(e)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(f)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(g)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(h)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(i)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(j)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(k)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

(l)

Interpretation Introduction

Interpretation:

The major product for the given reaction should be identified.

Concept introduction:

Bromination:

Alcohols brominated by using Pbr3 which provides corresponding brominated products.

Chlorination:

Alcohols chlorinated by using thionyl chloride and pyridine which provides corresponding chlorinated products.

Similarly, alcohols can be chlorinated by using hydrochloric acid and zinc chloride which provides corresponding chlorinated products.

E1 Elimination: Formation of alkene from alkyl bromide or alcohol through the formation of stable carbocation followed by elimination.

Oxidation: Alcohols undergoing oxidation by using oxidizing agent like PCC (Pyridinium Chlorochromate) in dichloromethane which provides aldehyde.

Alcohols undergoing oxidation by using oxidizing agent like Na2Cr2O7 (chromic acid) which provides carboxylic acid.

Alcohols is protected by using variety of reaction for example, Alcohols can be protected by treating with tosyl chloride in presence of base. Similarly it can be protected by using TMSCl in presence of base.

Alcohols treated with any metals or base which provides alkoxide.

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Chapter 13 Solutions

Organic Chemistry

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