Chapter 11, Problem 11.14P

Interpretation Introduction

(a)

Interpretation: The products that are formed by the reaction of the given terminal alkyne, with [1] ${\text{H}}_{\text{2}}\text{O}$, ${\text{H}}_{\text{2}}{\text{SO}}_4$ and ${\text{HgSO}}_{\text{4}}$ or [2] ${\text{R}}_{\text{2}}\text{BH}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$, ${}^{-}\text{OH}$ are to be drawn.

Concept introduction: A stepwise procedure of transforming an alkyne into a carbonyl group is known hydroboration-oxidation reaction. In a hydroboration-oxidation reaction, a terminal alkyne reacts with ${\text{R}}_{\text{2}}\text{BH}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$, ${}^{-}\text{OH}$ to form an aldehyde.

A terminal alkyne reacts with ${\text{H}}_{\text{2}}\text{O}$, ${\text{H}}_{\text{2}}{\text{SO}}_4$ (strong acid) and ${\text{HgSO}}_{\text{4}}$ to form a ketone.

Interpretation Introduction

(b)

Interpretation: The products that are formed by the reaction of the given terminal alkyne, with [1] ${\text{H}}_{\text{2}}\text{O}$, ${\text{H}}_{\text{2}}{\text{SO}}_4$ and ${\text{HgSO}}_{\text{4}}$ or [2] ${\text{R}}_{\text{2}}\text{BH}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$, ${}^{-}\text{OH}$ are to be drawn.

Concept introduction: A stepwise procedure of transforming an alkyne into a carbonyl group is known hydroboration-oxidation reaction. In a hydroboration-oxidation reaction, a terminal alkyne reacts with ${\text{R}}_{\text{2}}\text{BH}$ followed by ${\text{H}}_{\text{2}}{\text{O}}_{\text{2}}$, ${}^{-}\text{OH}$ to form an aldehyde.

A terminal alkyne reacts with ${\text{H}}_{\text{2}}\text{O}$, ${\text{H}}_{\text{2}}{\text{SO}}_4$ (strong acid) and ${\text{HgSO}}_{\text{4}}$ to form a ketone.