An organic compound C_8H_{12} on ozonolysis g | vedclass

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(C) The molecular formula $C_8H_{12}$ indicates a degree of unsaturation of $2$. Ozonolysis of the compound yields $2 \ moles$ of $3-$oxobutanal $(CH_

Vedclass · Accepted Answer

$1,2-$dimethylcyclohexa$-1,4-$diene

Vedclass · Answer

(C) The molecular formula $C_8H_{12}$ indicates a degree of unsaturation of $2$. Ozonolysis of the compound yields $2 \ moles$ of $3-$oxobutanal $(CH_3COCH_2CHO)$. This implies the original compound must be a cyclic diene that,upon cleavage of its two double bonds,produces two identical fragments of $3-$oxobutanal. $1$,$4$-dimethylcyclohexa$-1,4-$diene (Option $A$) on ozonolysis gives $2 \ moles$ of $3-$oxobutanal. $1$,$5$-dimethylcyclohexa$-1,4-$diene (Option $B$) is the same as $1,4-$dimethylcyclohexa-$1,4-$diene. $1$,$2$-dimethylcyclohexa$-1,4-$diene (Option $C$) on ozonolysis gives $1 \ mole$ of $2,3-$dioxobutane and $1 \ mole$ of $1,4-$butanedial. $2$,$3$-dimethylcyclohexa$-1,3-$diene (Option $D$) on ozonolysis gives $1 \ mole$ of $2,3-$dioxobutane and $1 \ mole$ of $1,4-$butanedial. Since the question asks for the structure that $CAN$ $NOT$ be the compound,and both $C$ and $D$ do not yield $3-$oxobutanal,there is an ambiguity in the provided options. However,based on standard chemistry problems of this type,$1,4-$dimethylcyclohexa-$1,4-$diene is the intended structure that $DOES$ produce $3-$oxobutanal. Given the options,$C$ and $D$ are incorrect structures.

An organic compound $C_8H_{12}$ on ozonolysis gives $2 \ moles$ of $3-$oxobutanal. Then the structure of the compound can not be

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