Single Choice

Arrange the following in the increasing order of expected enol content. $$i.$$ $$CH_3COCH_2CHO$$ $$ii.$$ $$CH_3COCH_3$$ $$iii.$$ $$CH_3CHO$$ $$iv.$$ $$CH_3COCH_2COCH_3$$

A$$iii < i < ii < iv$$
B$$iii < ii < i < iv$$
Correct Answer
C$$i < iv < ii < iii$$
D$$iv < i < ii < iii$$

Solution

Order of enol content:
Aldehyde < Ketone < Keto-aldehyde < Diketone $$(iii < ii < i < iv)$$
Enol formation is possible is there is hydrogen on alpha-carbon to carbonyl group. So, enol formation is more likely for ketone compared to aldehyde. Now, in case of a diketone, hydrogen bonding occurs in the enol form which stabilizes it more compared to keto form. So, it is the most stable followed by keto-aldehyde. Then comes ketone and ultimately aldehyde.

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