Question

For each compound, give the product(s) expected from (1) HgSO₄/H₂SO₄– catalyzed hydration and (2) hydroboration–oxidation.

(a) hex-1-yne

(b) hex-2-yne

(c) hex-3-yne

(d) cyclodecyne

Short answer

Alkyne is hydrated using the Kucherov reaction using the reagent dilute sulphuric acid and special reagent mercury sulfate HgSO₄/H₂SO₄ .

Hydration of alkyne follows Markovnikov's rule, and intermediate enol is formed during the reaction.

Step-by-step solution

Hydration of Alkyne

Alkyne is hydrated using the Kucherov reaction using the reagent dilute sulphuric acid and special reagent mercury sulfate HgSO₄/H₂SO₄ .

Hydration of alkyne follows Markovnikov's rule, and intermediate enol is formed during the reaction.

Products from HgSO4/H2SO4 - catalyzed hydration

(a) HgSO₄/H₂SO₄catalyzed reaction of hex-1-yne from hex-2-one product.

(b) HgSO₄/H₂SO₄catalyzed reaction of hex-2-yne from a mixture of two products hex-2-one and hex-3-one.

(c) HgSO₄/H₂SO₄catalyzed reaction of hex-3-yne from hex-3-one product

(d) HgSO₄/H₂SO₄catalyzed reaction of cyclodecyne forms cyclodecaone product.

Products from the hydroboration oxidation reaction

(a) Hydroboration oxidation reaction of hex-1-yne from hexanone product.

The hydroboration oxidation reaction of (a)

(b) Hydroboration oxidation reaction of hex-2-yne from a mixture of two products hex-2-one and hex-3-one.

(c) Hydroboration oxidation reaction of hex-3-yne from hex-3-one product.

(d) Hydroboration oxidation reaction of cyclodecyne forms cyclodecaone product