The structure of intermediate A in the following reaction is: C6H5CH(CH3)2 + O2 -> A A ->[H+/H2O] C6H5OH + CH3COCH3

Correct answer: (B) (B) C6H5-C(CH3)2-O-O-H. Answer: (B) C6H5-C(CH3)2-O-O-H (cumene hydroperoxide) Solution: In the cumene process, air O2 oxidises the benzylic (3^°) C-H of cumene to form cumene hydroperoxide (2-phenylpropan-2-yl hydroperoxide), the intermediate A: C6H5CH(CH3)2 + O2 -> C6H5C(CH3)2OOH The benzylic position is attacked because the resulting radical/peroxide is stabilised. On treatment with H+/H2O, A rearranges (via migration of the aryl group) and hydrolyses to phenol and acetone: C6H5C(CH3)2OOH ->[H+/H2O] C6H5OH + CH3COCH3

NEET 2019 · ChemistryPrevious Year Question

The structure of intermediate A in the following reaction is: $C X_{6} H X_{5} CH (CH X_{3}) X_{2} + O X_{2} A$ $A H X^{+} / H X_{2} O C X_{6} H X_{5} OH + CH X_{3} COCH X_{3}$

Answer: (B) (B) $C X_{6} H X_{5} - C (CH X_{3}) X_{2} - O - O - H$ . \textbf{Answer:} (B) $C X_{6} H X_{5} - C (CH X_{3}) X_{2} - O - O - H$ (cumene hydroperoxide) \textbf{Solution:} In the cumene process, air $O X_{2}$ oxidises the benzylic ( $3^{\circ}$ ) $C - H$ of cumene to form cumene hydroperoxide (2-phenylpropan-2-yl hydroperoxide), the intermediate A: $C X_{6} H X_{5} CH (CH X_{3}) X_{2} + O X_{2} C X_{6} H X_{5} C (CH X_{3}) X_{2} OOH$ The benzylic position is attacked because the resulting radical/peroxide is stabilised.

A.(A) $C X_{6} H X_{5} - O - CH (CH X_{3}) X_{2}$
B.(B) $C X_{6} H X_{5} - C (CH X_{3}) X_{2} - O - O - H$ ✓
C.(C) $C X_{6} H X_{5} - O - O - CH (CH X_{3}) X_{2}$
D.(D) $C X_{6} H X_{5} - CH X_{2} - C (CH X_{3}) (OOH) H$

Correct Answer

(B) (B) $C X_{6} H X_{5} - C (CH X_{3}) X_{2} - O - O - H$

Solution & Explanation

\textbf{Answer:} (B) $C X_{6} H X_{5} - C (CH X_{3}) X_{2} - O - O - H$ (cumene hydroperoxide) \textbf{Solution:} In the cumene process, air $O X_{2}$ oxidises the benzylic ( $3^{\circ}$ ) $C - H$ of cumene to form cumene hydroperoxide (2-phenylpropan-2-yl hydroperoxide), the intermediate A: $C X_{6} H X_{5} CH (CH X_{3}) X_{2} + O X_{2} C X_{6} H X_{5} C (CH X_{3}) X_{2} OOH$ The benzylic position is attacked because the resulting radical/peroxide is stabilised. On treatment with $H X^{+}$ / $H X_{2} O$ , A rearranges (via migration of the aryl group) and hydrolyses to phenol and acetone: $C X_{6} H X_{5} C (CH X_{3}) X_{2} OOH H X^{+} / H X_{2} O C X_{6} H X_{5} OH + CH X_{3} COCH X_{3}$

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The structure of intermediate A in the following reaction is: CX6​HX5​CH(CHX3​)X2​+OX2​​A AHX+/HX2​O​CX6​HX5​OH+CHX3​COCHX3​

Solution & Explanation

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The structure of intermediate A in the following reaction is: $C X_{6} H X_{5} CH (CH X_{3}) X_{2} + O X_{2} A$ $A H X^{+} / H X_{2} O C X_{6} H X_{5} OH + CH X_{3} COCH X_{3}$