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(C) The reaction of toluene with $Na$ in liquid $NH_3$ is a Birch reduction,which reduces the benzene ring to $1-$methyl$-1,4-$cyclohexadiene. Ozonoly

Vedclass · Accepted Answer

$CH_3-CH(CHO)-CHO$

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(C) The reaction of toluene with $Na$ in liquid $NH_3$ is a Birch reduction,which reduces the benzene ring to $1-$methyl$-1,4-$cyclohexadiene. Ozonolysis of $1-$methyl$-1,4-$cyclohexadiene followed by reductive workup $(O_3/Zn)$ cleaves the double bonds to produce $CH_3-CO-CH_2-CHO$ and $OHC-CH_2-CHO$ (which is $O=CH-CH_2-CHO$). Since both $CH_3-CO-CH_2-CHO$ and $O=CH-CH_2-CHO$ are obtained as products,option $C$ $(CH_3-CH(CHO)-CHO)$ cannot be obtained. Thus,the correct answer is $C$.

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

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