1-Hexyne

1-Hexyne is a hydrocarbon consisting of a straight six-carbon chain having a terminal alkyne. Its molecular formula is. A colorless liquid, it is one of three isomers of hexyne. It is used as a reagent in organic synthesis.

Synthesis and reactions

1-Hexyne can be prepared by the reaction of monosodium acetylide with butyl bromide:
Its reactivity illustrates the behavior of terminal alkylacetylenes. The hexyl derivative is common test substrate because it is conveniently volatile. It undergoes deprotonation at C-3 and C-1 with butyl lithium:
This reaction allows alkylation at the 3-position.
Catechol borane adds to 1-hexyne to give the 1-hexenyl borane.
1-Hexyne reacts with diethyl fumarate to produce.