EBK ORGANIC CHEMISTRY
EBK ORGANIC CHEMISTRY
8th Edition
ISBN: 8220102744127
Author: Bruice
Publisher: PEARSON
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Chapter 19, Problem 38P

(a)

Interpretation Introduction

Interpretation:

The product obtained in skraup synthesis by replacing aniline with para-ethylaniline has to be given.

Concept Introduction:

Skraup synthesis is the reaction of aniline with an alpha-beta unsaturated carbonyl compound and proceeds through the formation of carbocation and results in the formation of cyclic ring which on reduction gives quinoline.

(b)

Interpretation Introduction

Interpretation: The product obtained in skraup synthesis by replacing glycerol with 3-hexen-2-one has to be given.

Concept Introduction:

Skraup synthesis is the reaction of aniline with an alpha-beta unsaturated carbonyl compound and proceeds through the formation of carbocation and results in the formation of cyclic ring which on reduction gives quinoline.

(c)

Interpretation Introduction

Interpretation: The reactants required for the preparation of 2,7-diethyl-3-methylquinoline in skraup synthesis should be given.

Concept Introduction:

Skraup synthesis is the reaction of aniline with an alpha-beta unsaturated carbonyl compound and proceeds through the formation of carbocation and results in the formation of cyclic ring which on reduction gives quinoline.

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Quinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring, are commonly synthesized by a method known as the Skraup synthesis, in which aniline reacts with glycerol under acidic conditions. Nitrobenzene is added to the reaction mixture to serve as an oxidizing agent. The first step in the synthesis is the dehydration of glycerol to propenal. a. What product would be obtained if para-ethylaniline were used instead of aniline? b. What product would be obtained if 3-hexen-2-one were used instead of glycerol? c. What starting materials are needed for the synthesis of 2,7-diethyl-3-methylquinoline?
Quinolines, heterocyclic compounds that contain a pyridine ring fused to a benzene ring, are commonly synthesized by a method known as the Skraupsynthesis, in which aniline reacts with glycerol under acidic conditions. Nitrobenzene is added to the reaction mixture to serve as an oxidizing agent.The first step in the synthesis is the dehydration of glycerol to propenal. a. What product would be obtained if para-ethylaniline were used instead of aniline?b. What product would be obtained if 3-hexen-2-one were used instead of glycerol?c. What starting materials are needed for the synthesis of 2,7-diethyl-3-methylquinoline?
Which could explain the stronger acidity of phenols compared to alcohols. Why? a.pi-electron delocalization b.steric effect c.hydrogen bonding d.hyperconjugation

Chapter 19 Solutions

EBK ORGANIC CHEMISTRY

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