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Chapter 18: Q 81 P (page 919)

Question: Describe how naphthalene can be prepared from the given starting material.

Short Answer

Expert verified

The presence of activating substituents enhances the reactivity of the benzene towards electrophilic substitution reactions. The presence of deactivating substituents reduces the reactivity of the benzene ring.

Some activating substituents are -NH2 and -OR, and some deactivating substituents are -COOH,-CHO, etc.

Step by step solution

01

Electrophilic aromatic substitution

The presence of activating substituents enhances the reactivity of the benzene towards electrophilic substitution reactions. The presence of deactivating substituents reduces the reactivity of the benzene ring.

Some activating substituents are -NH2 and -OR, and some deactivating substituents are -COOH,-CHO, etc.

02

Preparation of naphthalene from the given starting material

The given compound, 4-phenylbutanoyl chloride, reacts with AICH3 and H2O to form 3,4-dihydronaphthalen-1(2H)-one. This reacts with Pd/C and H2 to form 1,2,3,4-tetrahydronaphthalene.

This reacts with Br2 and light to form 1-bromo-1,2,3,4-tetrahydronaphthalene. This further reacts with tert-BuO- to form 1,2-dihydronaphthalene. This reacts with NBS, peroxide, and heat to form 2-bromo-1,2-dihydronaphthalene. This reacts with tert-BuO- to form naphthalene

Preparation of naphthalene from the given starting material

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Most popular questions from this chapter

Rank the following substituted anilines from most basic to least basic:

Explain why a diazonium group on a benzene ring cannot be used to direct an incoming substituent to the meta position.

Explain why hydroxide ion catalyzes the reaction of piperidine with 2,4-dinitroanisole but has no effect on the reaction of piperidine with 1-chloro-2,4-dinitrobenzene.

What is the major product(s) of each of the following reactions?

a. bromination of p-methylbenzoic acid

b. chlorination of o-benzenedicarboxylic acid

c. bromination of p-chlorobenzoic acid

d. nitration of p-fluoroanisole

e. nitration of p-methoxybenzaldehyde

f. nitration ofp-tert-butylmethylbenzene

The following tertiary alkyl bromides undergo anreaction in aqueous acetone to form the corresponding tertiary alcohols. Rank the alkyl bromides from most reactive to least reactive.
See all solutions

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