Chapter 11, Problem 28ASP

Interpretation Introduction

Interpretation: To determine the reaction sequence which best accomplishes the given transformation.

Concept introduction:

• The reaction used in the given conversions are:
• Hydroboration of alkenes by ${\text{BH}}_{\text{3}}{\text{THF/H}}_{\text{2}}{\text{O}}_{\text{2}}\text{/NaOH}$ produces fewer substituted alcohols.
• $\text{HBr/ROOR}$ follows the anti-Markovnikov rule for the addition of $\text{HBr}$ to give alkyl halide.
• Sodium acetylide reacts with alkyl halide groups to give alkynes.
• Treatment of alcohol with $\text{TsCl}$, usually in the presence of a weak base such as pyridine, results in sulfonate esters.
• Lindlar's Catalyst transforms an alkyne into a cis alkene.
• Hydroboration of terminal alkynes by ${\text{R}}_{\text{2}}{\text{BH/H}}_{\text{2}}{\text{O}}_{\text{2}}\text{/NaOH }$ produces aldehyde.