Chapter 9.14, Problem 15P

Interpretation Introduction

Interpretation:

A method for synthesis of ${\text{(E)-H}}_{\text{2}}{\text{C=CHCH}}_{\text{2}}{\text{CH}}_{\text{2}}{\text{CH=CHCH}}_{\text{3}}$ from propyne, organic compounds containing four carbons or less, and any inorganic reagents is to be outlined.

Concept introduction:

Terminal alkynes can be deprotonated with strong bases like amide ion, giving acetylides which can act as nucleophiles.

Acetylide ion reacts with a primary alkyl halide producing a new alkyne with more carbon atoms.

Partial reduction of alkynes with sodium in liquid ammonia converts the triple bond to a trans double bond.