Answered: NH2 H2SO4 CH, —СН—СН, 1. CH,=CH-CH=0 2.…

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NH2 H2SO4 CH, —СН—СН, 1. CH,=CH-CH=0 2. -NO2 ОН 2 H,O glycerol НО НО quinoline

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter19: Aldehydes And Ketones: Nucleophilic Addition Reactions

Section19.SE: Something Extra

Problem 55AP: Draw and name the seven aldehydes and ketones with the formula C5H10O. Which are chiral?

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Concept explainers

Diol

In chemistry there are so many chemical compounds that have a hydroxyl group but a chemical compound having two hydroxyl groups (-OH) is termed as a diol. It also implies the presence of two alcohols whereas polyols contain two or more than two hydroxyl groups (-OH). Glycol or 1,2-diol is an aliphatic diol that has two alcohol groups on adjacent carbon atoms. In industries, the most commonly used diol is ethylene glycol.

Question

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?

NH2
H2SO4
CH, —СН—СН,
1.
CH,=CH-CH=0
2.
-NO2
ОН
2 H,O
glycerol
НО НО
quinoline

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