Alkyne Hydration Practice Problems

Show the ketone that forms when each alkyne undergoes an oxymercuration reaction.

(a) 5-methylhept-1-yne

(b) 1,8-dicyclopentyloct-4-yne

Acid-catalyzed hydration of alkynes in the presence of HgSO₄ produces ketones as products. Identify one possible alkyne which deviates from this rule and produces an aldehyde instead.

Show how the following synthetic transformation can be accomplished. Give the structures of all intermediates.
but-1-yne → butan-2-one

Oxymercuration-reduction is an excellent method for obtaining single compounds from the hydration of symmetrical internal or terminal alkynes. Draw the product of the oxymercuration-reduction reaction for the following compound:

1-pentyne

Oxymercuration-reduction is an excellent method for obtaining single compounds from the hydration of symmetrical internal or terminal alkynes. Draw the products of the oxymercuration-reduction reaction for the following compound:

2-pentyne

Show how hex-1-yne can be converted to hexanal. Provide any necessary reagents.

Show how 1-bromobutane can be converted to hexanal. Provide any necessary reagents.

Identify the reagent required to complete the syntheses shown below.

Consider the following aldehyde:

Is it possible to synthesize the aldehyde from an alkyne with a yield greater than 50%? If so, provide the synthetic scheme.

Consider the following aldehyde:

Is it possible to synthesize the aldehyde from an alkyne with a yield greater than 50%? If so, provide the synthetic scheme.

Provide the best alkyne to use to produce each of the following ketones.

Provide the best alkyne to use for the synthesis of the ketone below.

Propose a way to synthesize the product shown using the provided starting molecule, any inorganic reagents, and any organic molecule with only 4 carbons or fewer.

Provide the product/s when 2-methyloct-3-yne goes through acid-catalyzed hydration.

Identify the products of the reaction shown below.