JEE Advanced 2015 · Paper 2 · Chemistry Q30 · Dronacharya Exams

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ChemistryMultiple correct+4 / -2Question 30 of 60

The major product U in the following reactions is

Benzene with CH₂=CH-CH₃, H⁺ under high pressure and heat gives T; T with a radical initiator and O₂ gives U.

A

1-Phenylpropyl hydroperoxide: Ph-CH(OOH)-CH₂CH₃.

B

Cumene hydroperoxide: Ph-C(CH₃)₂-OOH.

C

1-Phenylprop-2-enyl hydroperoxide: Ph-CH(OOH)-CH=CH₂.

D

2-Phenylallyl hydroperoxide: Ph-C(=CH₂)-CH₂-OOH.

Answer and worked solution

Official answer: B

T: Friedel-Crafts alkylation of benzene with propene/H⁺ goes through the isopropyl cation, giving cumene.
U: radical autoxidation at the tertiary benzylic C-H gives cumene hydroperoxide, $\ce{PhC(CH3)2OOH}$ .

(B)

Topics:Phenols Aromatic hydrocarbons and electrophilic substitution

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