Organic Chemistry - Standalone book
Organic Chemistry - Standalone book
10th Edition
ISBN: 9780073511214
Author: Francis A Carey Dr., Robert M. Giuliano
Publisher: McGraw-Hill Education
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Chapter 22, Problem 48P
Interpretation Introduction

Interpretation:

The synthesis of the given compound by using nitrobenzene, p-nitrobenzyl alcohol or p-nitrotoluene as a starting material has to be stated.

Concept Introduction:

The substitution reaction involves the replacement of one functional group by another functional group. In nucleophilic substitution, an electron rich species attacks the species that is deficient in electrons.

In a nucleophilic substitution reaction, the electrophile and the leaving group together form a substrate. The nucleophile attacks over the substrate and there occurs the removal of leaving group from the substrate.

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(a) Propose a reasonable synthesis for the formation of nonane from CH3CH2CH2I and  any other organic/inorganic reagent. (b) Suggest three (3) different Grignard reactions leading to 2-phenyl-2-butanol.
The hydrocarbon fluorene was treated with potassium t-butoxide in an acid-base reaction, giving the fluorenide anion and t-butyl alcohol. (a) Which way does the equilibrium lie, and by how much? b) What is the proportion of the fluorenide anion to fluorene? (c) Why is fluorene so highly acidic, considering the pKa of an average alkane is above 50?
(a) Account for the following :(i) Propanal is more reactive than propanone towards nucleophilic reagents.(ii) Electrophilic substitution in benzoic acid takes place at meta position.(iii) Carboxylic acids do not give characteristic reactions of carbonyl group.(b) Give simple chemical test to distinguish between the following pairs of compounds:(i) Acetophenone and benzaldehyde(ii) Benzoic acid and ethylbenzoate.
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