The final product, $D$ in the above sequence of reactions is:

C H_{3} C H (C H_{3}) O H

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(C H_{3})_{2} C H O H

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(C H_{3})_{2} C H C H_{2} C H_{2} O H

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(C H_{3})_{2} C H O C H_{2} C H_{3}

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Solution

The correct option is C $(C H_{3})_{2} C H C H_{2} C H_{2} O H$
A) Substitution reaction takes place at the carbon attached to the $- O H$ group. The product is $(C H_{3})_{2} - C H - B r$ .
B) Mg gets inserted between $C$ and $B r$ , leading to the formation of the Grignard reagent. The product is $(C H_{3})_{2} - C H - M g B r$ .
C) Grignard reagent reacts with an epoxide. The product is $(C H_{3})_{2} - C H - C H_{2} - C H_{2} - O M g B r$ .
D) Hydrolysis takes place here. The product is $(C H_{3})_{2} - C H - C H_{2} - C H_{2} - O H$ .

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D

C H_{3} - C N d i l . H C l - --- \to A L i A l H_{4} - --- \to B P C l_{5} - -- \to C A l c . K O H - ----- \to D

D

F

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