Which of the alkynes below, after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields? 4-methyl-1-pentyne 1-hexyne 3-methyl-1-pentyne 3-hexyne 2-hexyne?

We have to get the correct alkyne which after undergoing an acid-catalyzed hydration, would be expected to produce two different ketones in nearly equivalent yields.

The answer is: 2-hexyne

Acid catalyzed hydration of alkyne produces ketone (except acetylene, as only acetylene gives aldehyde on hydration).

2-Hexyne on hydrolysis produces 2-hexanone and 3-hexanone where they both are ketones and they both are different ketones.

4-methyl-1-pentyne gives 4-methyl-2-pentanone and 4-methyl-1-pentanal (non equivalent mixture), where both are not ketones, one aldehyde and one ketone.

1-hexyne gives 2-hexanone and 1-hexanal where one is ketone and other one is aldehyde.

3-methyl-1-pentyne gives 3-methyl-2-pentanone and 3-methyl-1-pentanal (non equivalent mixture), where both are not ketones, one aldehyde and one ketone.

3-hexyne gives two equivalent amount of  3-hexanone.

answers: to make sure that all of the broken pieces of tablet were added to the water, to allow for fair comparison of all three trials, with different particle sizes to avoid experimental error