Organic Chemistry
Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter SRP, Problem 6P
Interpretation Introduction

Interpretation:

The synthesis for the given products is to be outlined by using 1-butanol as starting compound.

Concept introduction:

Thionyl chloride and phosphorous bromide reacts with alcohol to yield alkyl chloride and bromides respectively.

Sodium cyanide is used to convert halo alkane to the corresponding nitrile.

Lithium aluminum hydride is a reducing agent, used to selectively convert nitrile to amine.

Potassium permanganate is an oxidizing agent useful in converting alcohols to acid.

Hofmann rearrangement is used for converting primary amide to amine with one less carbon.

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(a) Although phenoxide ion has more number of resonating structures than carboxylate ion, carboxylic acid is a stronger acid than phenol. Give two reasons.(b) How will you bring about the following converstions?(i) Propanone to propane                      (ii) Benzoyl chloride to benzaldehyde(iii) Ethanal to but-2-enal
(a) How will you obtain the following :(i) Benzaldehyde from Phenol             (ii) Benzoic acid from Aniline(b) Give reasons :(i) Aldehydes are more reactive than ketones towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give the characteristic reactions of carbonyl group.

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