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Chapter 18: Q3P (page 873)

Propose a mechanism for the following reaction:

Short Answer

Expert verified

The answer is,

Mechanism

Step by step solution

01

Electrophilic addition

The electrophilic addition of the aromatic system involves the formation of a new sigma bond by the breaking of a pi bond in it. The electrophiles are the electron-deficient species. The double bonds in the benzene ring undergo addition to the electrophiles forming the cation system, which will regain aromaticity by removing protons.

02

Explanation

The mechanism for the given reaction is shown below.

Mechanism

The mechanism involves the electrophilic addition to the benzene ring. The benzene protons are then removed to regain the aromaticity of the ring. This is repeated until all the hydrohen is replaced with the Deuterium atom.

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Most popular questions from this chapter

Give the products, if any, of each of the following reactions:

a. benzonitrile + methyl chloride + ${AlCl}_{3}$

b. phenol + ${Br}_{2}$

c. benzoic acid + ${CH}_{3} {CH}_{2} Cl$ + ${AlCl}_{3}$

d. benzene + 2 ${CH}_{3} Cl$ + ${AlCl}_{3}$

Are the following substituents ortho–para directors or meta directors?

a. $CH = CHC \equiv N$

b. ${NO}_{2}$

c. ${CH}_{2} OH$

d. $COOH$

e. ${CF}_{3}$

f. $N = O$

What are the products of the following reactions?

Draw the structure for each of the following:

a. m-ethylphenol

b. p-nitrobenzenesulfonic acid

c. (E)-2-phenyl-2-pentene

d. o-bromoaniline

e. 4-bromo-1-chloro-2-methylbenzene

f. m-chlorostyrene

g. o-nitro anisole

i. 2,4-dichloromethylbenzene

f. m-chlorobenzoic acid

Use the four compounds shown below to answer the following questions:

Why are the ortho-halo-substituted benzoic acids stronger acids than benzoic acid?
Why is o-fluorobenzoic acid the weakest of the ortho-halo-substituted benzoic acids?
Why do o-chlorobenzoic acid and o-bromobenzoic acid have similar pKa values?

See all solutions

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