Maximum enol content is in:

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

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

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

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$P h - O | | C - C H_{2} - O | | C - P h$

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Solution

The correct option is D
$P h - O | | C - C H_{2} - O | | C - P h$

Enol forms of both a and b exists,but the content is lower than the aldehyde and ketone groups respectively.This is because the -c- bond is highly stable.

c) exhibits a stable enol form so its content will be more than a & b.This is because of chelation.

The H bonding between O-H &-C- in the enol form further stabilizes the compound in addition to the conjugate alternative.

d) also exhibits chelation but enol content is even more than C owing to extended conjugate bonds (alternative sinlge-double-single-double).

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C H_{3} - C \equiv C - C H_{3} (i) X - ------ \to (i i) H_{2} O / Z n C H_{3} - C | | O - C | | O - C H_{3}; X

C H_{3} - C \equiv C - C H_{3} (i) X - ------ \to (i i) Z n / H_{2} O C H_{3} - C | | O - C | | O - C H_{3}

X

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

C H_{2} =^{-} - C H_{3}

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

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