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1-Hexyne
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1-Hexyne is a hydrocarbon consisting of a straight six-carbon chain having a terminal alkyne. Its molecular formula is HC2C4H9. 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:
NaC2H + BrC4H9 → HC2C4H9 + NaBr
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:
HC2C4H9 + 2 BuLi → LiC2CH(Li)C3H7 + 2 BuH
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 n-hexylsuccinic acid.
== See also ==
2-Hexyne
3-Hexyne
== References ==