What is the major product obtained from the acid-catalyzed hydration of #CH_3CH_2CH_2CH=CHCH_3#?

1 Answer
Nov 9, 2014

The major product is probably hexan-2-ol.

The cations formed are CH₃CH₂CH₂CH⁺-CH₂CH₃ and CH₃CH₂CH₂CH₂CH⁺-CH₃.

There is not much difference in stability, because both are 2° carbocations.

But the first structure has four β hydrogens to stabilize the carbocation. The second structure has five β hydrogens.

So the second structure may be a bit more stable.

I would expect the major product to be hexan-2-ol rather than hexan-3-ol, but not by an large amount.