EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG
4th Edition
ISBN: 9781119659525
Author: Klein
Publisher: WILEY CONS
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Chapter 22, Problem 83IP
Interpretation Introduction

Interpretation: The preparation of the given compound from benzene, ammonia and other reagents has to be achieved via epoxide formation

Concept Introduction:

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 ammonia in the presence of sodium cyanoborohydride as a reducing agent and a proton source in the reaction medium to produce primary amines.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 83IP , additional homework tip  1

Friedel–Crafts Acylation: The Friedel–Crafts acylation is the reaction of an arene with acyl chlorides or anhydrides using a strong Lewis acid catalyst. This reaction proceeds via electrophilic aromatic substitution to form monoacylated products.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 83IP , additional homework tip  2

Grignard reaction: The Grignard reaction is an organic reaction used to create a variety of products through the reaction of an organomagnesium compound, also known as a "Grignard reagent" with an electrophile, followed by acid work-up.

Concentrated sulfuric acid acts as a dehydrating agent.  Concentrated sulfuric acid and heat remove a water molecule in a compound.  Peroxy acid forms an epoxide with an alkene.  Primary or secondary amines will attack epoxides in a ring-opening process.  For substituted epoxides, nucleophilic attack generally takes place at the less sterically hindered side of the epoxide.

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 83IP , additional homework tip  3

To find: Prepare the given compound from benzene, ammonia and other reagents via epoxide formation

Apply a retrosynthetic analysis

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG, Chapter 22, Problem 83IP , additional homework tip  4

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Chapter 22 Solutions

EBK ORGANIC CHEMISTRY-STUD.SOLNS.MAN+SG

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