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98%, Sat 2:46 PM Bookmarks People Window Help tfn Quiz x le 28 5264&pag; 3 You logged in as Winter 2017) Reactivity Quiz 2B Benzene Chemistry Review The chemical mechanism of side chain oxidation in al benzenes by chromic acid is somewhat mysterious. It is well known that for red the reaction to occur, at least one benzyic hydrogen should be present in the side chain, and it is thought that the oxidaton of the akyl group all toward oxidation as the initialaky 100 the way down to carboxylic acid is a process that involves intermedates that are at least 5 One method chemical mechanism of organic reactions, and elucidate the nature of he rate determining step involves the powerful to study the is called the Kinetic comparison the reaction rates the and The ratio the constants the observed KE Effect Dierent reacton mechanism give dinerent values for the KE the comparison of the numeric of with values predicted theoretoally for a proposed mechanism allows one to judge if the proposed mechanism is reasonable. It has been observed that the oxidation of diphenylmethane with chromic acid exhibits a large deuterium kinesc isotope the moleoule with the benzyic posion. two in the benzyic position 64 times of the large deutenum KE in the oxidation of following proposed models can be ruled out based on the observation diphenylmethane with chromic acid? The cleavage of the C-H bond occurs via a heterolytic mechanism in which an oxidizing species abstracts an hydride ion. b. The rate limiting step in the oxidation reaction is the loss of water from an intermediate (dphonymethanodio) in which two hydroxylgroups are attached to the benzylic carbon oxidizing and the benzylic carbon. c. The rate limiting step involves formaton of a new oxygen-carbon bond between the agent d. The rate limiting step in the oxidation reaction is the deavage of the benzylcc-H bond. e. The deavage of the cH bond ocours via a homolytic mechanism in which an oxiduzing spedes abstracts anhydrogen atom. Give your reasons

Explanation / Answer

Q.1: The mechanism for the oxidation of diphenyl methane is shown in the figure below:

From the above mechanism it is clear that:

The rate determining step in the oxidation reaction is the cleavage of the benzylic -C-H bond.

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