96% Sat 2:46 PM Bookmarks People Window le2 264 Reactity Quiz 2B: Benzene Chemis

Question

96% Sat 2:46 PM Bookmarks People Window le2 264 Reactity Quiz 2B: Benzene Chemistry Review is a white crystalline material with a rather pleasant geranium odor.Itis a valuable intermediate for the synthesis of various drugs and perfumes. One particulary interesting synthetic involves the preparation of modafnil (a wakefulness promoting drug) from 100 diphenylmethane after replacement of one of the benzyic hydrogens with bromine. This side chain bromination requires molocular b and aluminum trichloride Dphenylmethane can be prepared in a variety of ways. The textbooks approach involves the Friedel-crats acyation of beraene wth under reflux conditions followed by the treatment of the reaction product with hydrogen gas can be carried out in situ by adding aluminum amalgam over palladium on carbon. In the practice, the anematwe symthessofdpherymethane involves the use ofthe wurez-Feing reacton, in which into the acylation reaction mix. An benzyl chloride reacts with chlorobenzene in the presence of sodium in dryether Phenolic Minic Comasc ortho methylene dchlonde carbon monoxide and hydoc acid potassium permanganate Potassium cyanide oxidation of the reduction of the carbonyl of two benzene molecules acid hyd

Explanation / Answer

QUESTION 1

part 1

Modafinil is prepared by replacing the benzylic hydrogen of diphenylmethane. This is the hydrogen attached to the -CH2- group. (Your solution is correct)

part 2

Side chain bromination requires bromine molecule and UV radiation. This is a radical bromination reaction. Ypur answer is incorrect as you have used a halogen carrier. This will brominate the benzene ring.

part 3

To prepare diphenylmethane, benzyl chloride (C6H5-CH2-Cl) along with benzene is used. This is followed by reaction with hydrogen gas and palladium catalyst.

part 4

In practise the Gatterman-Koch reaction is carried out.

part 5

Wurtz-Fittig reaction allows the reaction of alkyl halides with arylhalides. Benzyl chloride is an alkyl halide and to form diphenylmethane, chlorobenzene is required.

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