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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

Use Figure 16-11 to explain why Friedel–Crafts alkylations often give polysubstitution but Friedel–Crafts acylations do not.

Refer to Table 6-3 on page 170 for a quantitative idea of the stability of a benzyl radical. How much more stable (in kJ/mol) is the benzyl radical than a primary alkyl radical? How does a benzyl radical compare in stability to an allylradical?

The nitroso group, - NO, is one of the few non-halogens that is an ortho- and para-directing deactivator. Explain this behaviour by drawing resonance structures of the carbocation intermediates in ortho, meta, and para electrophilic reaction on nitroso benzene,C6H5N=O.

Benzene and alkyl-substituted benzenes can be hydroxylated by reaction with H2O2in the presence of an acidic catalyst. What is the structure of the reactive electrophile? Propose a mechanism for the reaction.

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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