Which of the following product cannot be obtained in above reaction ?

H - O | | C - C H_{2} - O | | C - H

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C H_{3} - O | | C - C H_{2} - O | | C - H

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C H_{3} - C | C H O - O | | C - H

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None of these

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Solution

The correct option is D $C H_{3} - C | C H O - O | | C - H$
First birch reduction occurs where benzene is reduced to cyclohex-di-ene
Refer to image 01
Reductive ozonolysis of A using $O_{3} / Z n$ gives
Refer to image 02

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C H_{3} - O | | C - C H_{3} (A), C H_{3} - O | | C - H (B), C H_{3} - O | | C - C H_{2} - C l (C), H - O | | C - H (D), C l - C H_{2} - O | | C - H (E)

C H_{3} - O | | C - O - C H_{2} - C H_{3} + H - O \to (O = O_{18})

C H_{3} - O | | C - H (i); C H_{3} - O | | C - C H_{3} (i i); E t - O | | C - H (i i i)

C H_{3} - C H_{2} - C H_{2} - O | | C - H (i v); P h - O | | C - C H_{3} (v); P h - O | | C - P h (v i)

C H_{3} - C H_{2} - C H_{2} - O | | C - H

I . H N = C = O \leftrightarrow H - O - C \equiv N

I I . ¯ N = C = O \leftrightarrow N \equiv C - O^{-}

I I I . C H_{3} - O | | C - ¯ C H_{2} \leftrightarrow C H_{3} -^{-} C = C H_{2}

I V . C H_{3} - O | | C - C H_{3} \leftrightarrow C H_{3} - O H | C = C H_{2}

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