Question

Predict the initial and isolated products for the reaction. The starting material is a 6 carbon chain where there is a triple bond between carbons 3 and 4. This reacts with H 2 O, H 2 S O 4, and catalytic H g 2 plus to form an initial product. The initial product converts to the more stable isolated product but is in equilibrium. Hint: the products are isomers and in equilibrium with each other.

Answer 1

Answer:

See explanation and image attached

Explanation:

This reaction is known as mercuric ion catalyzed hydration of alkynes.

The first step in the reaction is attack of the mercuric ion on the carbon-carbon triple bond, a bridged intermediate is formed. This bridged intermediate is attacked by water molecule to give an organomercury enol. This undergoes keto-enol tautomerism, proton transfer to the keto group yields an oxonium ion, loss of the mercuric ion now gives equilibrium keto and enol forms of the compound. The keto form is favoured over the enol form.