ORGANIC CHEM PRINT STUDY GDE & SSM
ORGANIC CHEM PRINT STUDY GDE & SSM
4th Edition
ISBN: 9781119810650
Author: Klein
Publisher: WILEY
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Chapter 22, Problem 54PP

 (a)

Interpretation Introduction

Interpretation: The synthetic routes for the given transformations have to be proposed

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids.  This reaction is catalyzed by Lewis acids like anhydrous AlCl3, FeX3, ZnCl2, BF3 etc.

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  1

An azide synthesis: An azide synthesis involves the reaction between alkyl halide and sodium azide.  Alkyl azide is formed in the first step.  Alkyl azide on reduction with hydrogen in the presence of platinum produces primary amine.  In this way, primary amines are synthesized while secondary and tertiary amines are not formed as by-products.

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  2

Reductive amination: Sodium cyanoborohydride is a strong reducing agent than sodium borohydride.  It reduces the carbonyl group into amine group in a rapid way.  So, it is called as reductive amination reactions.  Aldehyde or ketone group is reacted with secondary amine in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce tertiary amines.

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  3

To find: Propose the synthetic routes for the given transformation (a)

Apply a retrosynthetic analysis

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  4

(b)

Interpretation Introduction

Interpretation: The synthetic routes for the given transformations have to be proposed

Concept Introduction:

Friedel-Crafts Alkylation: The Friedel-Crafts alkylation involves the electrophilic substitution of alkyl groups on aromatic rings when arenes are treated with alkyl halides in presence of Lewis acids.  This reaction is catalyzed by Lewis acids like anhydrous AlCl3, FeX3, ZnCl2, BF3 etc.

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  5

Sandmeyer reaction: Sandmeyer reactions use copper salts as the reagents.  Here, aryldiazonium salt is converted into aryl halides or aryl cyanides by using copper halides or copper cyanides.

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  6

A compound containing an amino group is treated with sodium nitrite and HCl leading to the formation of diazonium salt.

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  7

To find: Propose the synthetic routes for the given transformation (b)

Apply a retrosynthetic analysis

ORGANIC CHEM PRINT STUDY GDE & SSM, Chapter 22, Problem 54PP , additional homework tip  8

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Chapter 22 Solutions

ORGANIC CHEM PRINT STUDY GDE & SSM

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