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Chapter 16: Q16-21P (page 514)

How would you prepare diphenylmethane, (Ph)2CH2 , from benzene and an acid chloride?

Short Answer

Expert verified

Aromatic ring can activate benzylic carbonyl group towards reduction. The reduction of aryl alkyl ketones prepared by Friedelcraft鈥檚 acylation gets converted to alkylbenzene by hydrogenation over the palladium catalyst. Aryl alkyl ketone with a nitro substituent gets reduced to an amino group during the process of reduction in the presence of H2/Pd.

Step by step solution

01

Reduction of Aromatic Compounds 

Aromatic ring can activate benzylic carbonyl group towards reduction. The reduction of aryl alkyl ketones prepared by Friedelcraft鈥檚 acylation gets converted to alkylbenzene by hydrogenation over the palladium catalyst. Aryl alkyl ketone with a nitro substituent gets reduced to an amino group during the process of reduction in the presence of H2/Pd.

02

Preparing diphenylmethane from benzene and an acid chloride

Diphenylmethane can be prepared by reducing benzophenone withH2 /Pd. Benzophenone can be prepared by reacting benzene with benzoyl chloride in the presence of AlCl3(Friedal-Crafts acylation).The reaction can be given as:

Preparing diphenylmethane from benzene and an acid chloride

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Most popular questions from this chapter

Identify the carboxylic acid chloride that might be used in a Friedel鈥揅rafts acylation reaction to prepare each of the following acylbenzenes:

a.

b.

Starting with benzene as your only source of aromatic compounds,

how would you synthesize the following substances? Assume that you

can separate ortho and para isomers if necessary.

(a)p-Chloroacetophenone (b)m-Bromonitrobenzene

(c)o-Bromobenzenesulfonic acid (d)m-Chlorobenzenesulfonic acid

Acetanilide is less reactive than aniline toward electrophilic substitution. Explain

Rank the compounds in each of the following groups in order of their reactivity

to electrophilic substitution:

(a) Nitrobenzene, phenol, toluene, benzene

(b) Phenol, benzene, chlorobenzene, benzoic acid

(c) Benzene, bromobenzene, benzaldehyde, aniline

Electrophilic substitution on 3-phenylpropanenitrile occurs at theortho and para positions, but reaction with 3-phenylpropenenitrileoccurs at the meta position. Explain, using resonance structures of theintermediates.
See all solutions

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