Chapter 9.6, Problem 22ATS

Interpretation Introduction

Interpretation:

All possible structural isomers should be drawn for the given molecular formula ${\text{C}}_{\text{5}}{\text{H}}_{\text{10}}$ and need to select the isomers, which cannot give products with stereo isomer in hydroboration-oxidation reaction.

Concept introduction:

• Structural isomers: isomers that have same molecular formula and different structures are known as structural isomers.
• Hydroboration reaction: In this reaction water molecule is added across the double bond of the alkene in syn pathway. In hydroboration reaction, anti-Markovnikov’s product is favorable which means –OH group attached to less substituted carbon end of the alkene.
• Hydroboration reaction takes place in two steps; first step is syn addition of ${\text{BH}}_{\text{3}}$ and second step is attack of nucleophile (hydroxide ion produced from hydrogen peroxide and ${\text{BH}}_{\text{3}}$).