The compound shown below undergoes racemizati | vedclass

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(C) The compound is a chiral ketone. In the presence of an aqueous acid,the ketone undergoes keto-enol tautomerism. The acid protonates the carbonyl o

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(C) The compound is a chiral ketone. In the presence of an aqueous acid,the ketone undergoes keto-enol tautomerism. The acid protonates the carbonyl oxygen,followed by the removal of an $\alpha$-hydrogen to form an enol intermediate. The enol intermediate is planar at the $\alpha$-carbon,which removes the chirality at that center. When the enol tautomerizes back to the ketone,the proton can add from either side of the planar double bond,leading to the formation of both enantiomers,thus causing racemization. The structure representing the enol intermediate is $CH_3-C(OH)=C(OH)-CH_2CH_3$.

The compound shown below undergoes racemization on reaction with aqueous acid. Which of the following structures best represents the intermediate responsible for this process?

Similar Questions

The order of stability of carbonium ions is:

The decreasing order of stability of the following carbocations is:
$A$. $m-CH_3O-C_6H_4-CH_2^+$
$B$. $p-CH_3O-C_6H_4-CH_2^+$
$C$. $C_6H_5-CH_2^+$
$D$. $p-NO_2-C_6H_4-CH_2^+$

Which of the following is the most stable form for the given structure after rearrangement?

State True or False for the following statements:
$(i)$ Carbon possesses $sp^2$ hybridization in a carbocation.
$(ii)$ Carbon possesses $sp^3$ hybridization in a carbocation.
$(iii)$ $A$ carbocation is formed by homolytic fission of a bond.
$(iv)$ Carbocations are very stable.

Which of the following carbocations is least stable?

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