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Chapter 18: Q-18-5P (page 880)

What is the major product of a Friedel-crafts alkylation using the following alkyl chlorides?

a. CH3CH2Cl

b. CH3CH3CH2Cl

c. CH3CH2CH(Cl)CH3

d. (CH3)3CCl

e. (CH2)2CHCH2Cl

f. CH2CHCH2Cl

Short Answer

Expert verified

The answer is,

a.

b.

c.

d.

e.

f.

Step by step solution

01

Friedel Crafts Alkylation Reaction

The Friedel crafts alkylation reaction is the reaction in which an alkyl group gets substituted for a hydrogen atom in the benzene ring. It is an aromatic electrophilic substitution reaction, and the electrophile required is formed from the reaction of an alkyl halide with benzene in the presence of Aluminium chloride.

02

Subpart (a)

The major product of the Friedel crafts alkylation using the given alkyl chloride is shown below.

03

Subpart (b)

The major product of the Friedel crafts alkylation using the given alkyl chloride is shown below.

04

Subpart (c)

The major product of the Friedel crafts alkylation using the given alkyl chloride is shown below.

05

Subpart (d)

The major product of the Friedel crafts alkylation using the given alkyl chloride is shown below.

06

Subpart (e)

The major product of the Friedel crafts alkylation using the given alkyl chloride is shown below.

07

Subpart (f)

The major product of the Friedel crafts alkylation using the given alkyl chloride is shown below.

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Most popular questions from this chapter

An aromatic hydrocarbon with a molecular formula of C13H20has an 1H NMR spectrum with a signal at ~7 ppm that integrates to 5H. It also has two singlets; one of the singlets has 1.5 times the area of the second. What is the structure of the aromatic hydrocarbon?

Show how the following compounds can be synthesized from benzene:

a. m-chlorobenzenesulfonic acid

b. m-chloroethylbenzene

c. m-chlorobenzonitrile

d. 1-phenylpentane

e. m-bromobenzoic acid

f. m-hydroxybenzoic acid

g. p-cresol

h. benzyl alcohol

i. benzylamine

Propose a mechanism for each of the following reactions:

a.

b.

a. Rank the following esters from most reactive to least reactive in the first slow step of a nucleophilic acyl substitution reaction (formation of the tetrahedral intermediate):

b. Rank the same esters from most reactive to least reactive in the second slow step of a nucleophilic acyl substitution reaction (collapse of the tetrahedral intermediate).

Question: The pKa values of a few ortho-, meta-, and para-substituted benzoic acids are shown below:

The relative pKa values depend on the substituent. For chloro-substituted benzoic acids, the ortho isomer is the most acidic and the para isomer is the least

acidic; for nitro-substituted benzoic acids, the ortho isomer is the most acidic and the meta isomer is the least acidic; and for amino-substituted benzoic acids, the meta isomer is the most acidic and the ortho isomer is the least acidic. Explain these relative acidities.

a. Cl: ortho > meta > para

b. NO2: ortho > para > meta

c. NH2: meta > para > ortho
See all solutions

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