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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’s 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’s 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

Addition of HBr to 1-phenylpropene yields only (1-bromopropyl) benzene. Propose a mechanism for the reaction, and explain why none of the other regioisomer is produced.

Triphenylmethane can be prepared by reaction of benzene and chloroform in the presence of AlCl3. Propose a mechanism for the reaction.

4- chloropyridine undergoes reaction with dimethylamine to yield 4-dimethylaminopyridine. Propose a mechanism for the reaction.

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

Question: You know the mechanism of HBr addition to alkenes, and you know the effects of various substituent groups on aromatic substitution. Use this knowledge to predict which of the following two alkenes reacts faster with HBr. Explain your answer by drawing resonance structures of the carbocation intermediates.
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