Which of the following correctly identifies the two possible enol tautomers that can be formed from ?
A
and
B
and
C
and
D
and
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1
Identify the structure of 3-methyl-2-butanone, which is a ketone with a methyl group at carbon 3 and a carbonyl group at carbon 2 in a four-carbon chain.
Recall that enol tautomers form by the migration of an alpha hydrogen (a hydrogen on a carbon adjacent to the carbonyl) to the oxygen of the carbonyl group, creating a C=C double bond and an OH group.
Determine the alpha carbons adjacent to the carbonyl carbon (carbon 2). In 3-methyl-2-butanone, these are carbons 1 and 3, so enolization can occur at either position.
Draw the two possible enol forms: one with the double bond between carbons 2 and 3 and the OH on carbon 2 (3-methyl-2-buten-2-ol), and the other with the double bond between carbons 1 and 2 and the OH on carbon 1 (3-methyl-1-buten-2-ol).
Name these enol tautomers correctly by identifying the position of the double bond and the hydroxyl group, confirming that the two possible enols are 3-methyl-2-buten-2-ol and 3-methyl-1-buten-2-ol.