Question

Hydration of alkynes (via oxymercuration) gives good yields of single compounds only with symmetrical or asymmetrical alkynes. Show what products would be from hydration fo each compound.

(a) hex-3-yne

(b) hex-2-yne

(c) hex-1-yne

(d) cyclodecyne

(e) 3-methylcyclodecyne

Short answer

(a)

(b)

(c)

(d)

(e)

Step-by-step solution

Oxymercuration reaction

It is an electrophilic addition reaction that can transform an alkyne into an enol which tautomerizes into a ketone.

(alkyne) (enol) (ketone)

Tautomerism

Tautomerism is defined as the phenomenon in which a hydrogen atom is shifted from one place to another. This means that a single chemical compound can exist in two or more interconvertible structures. The making and breaking of a and bond is involved in tautomerism.

Formation of products

(a)

(b)

(c)

(d)

(e)