Chapter 14, Problem 14.12P

Interpretation Introduction

(a)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for cyclohexylacetylene are to be compared.

Concept introduction:

Hydroboration-oxidation reaction of an alkyne is the reaction in which an alkyne reacts with borane in presence of a peroxide to yield an enol which tautomerises to a corresponding aldehyde or a ketone. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.

Interpretation Introduction

(b)

Interpretation:

The hydroboration-oxidation and mercuric-ion catalysed hydration reaction for $\text{2-butyne}$ are to be compared.

Concept introduction:

Hydroboration-oxidation reaction is the reaction in which an alkene reacts with borane in presence of a peroxide to yield primary alcohol. The reaction occurs by Anti-Markovnikov’s rule. An alkyne can be converted into an aldehyde or a ketone by mercuric-ion catalysed hydration reaction. After the protonation of the alkynyl carbon, the water attacks as the nucleophile and an enol is formed. Enol is unstable and converts into a stable aldehyde or ketone.