1-Hexyne Explained

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:^[1]

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.^[2]

Catechol borane adds to 1-hexyne to give the 1-hexenyl borane.^[3]

1-Hexyne reacts with diethyl fumarate to produce .^[4]

See also

• 2-Hexyne
• 3-Hexyne

Notes and References

1. Kenneth N. Campbell, Barbara K. Campbell. 10.15227/orgsyn.030.0015. n-Butylacetylene . Organic Syntheses . 1950 . 30 . 15 .
2. 10.15227/orgsyn.058.0001. A. J. Quillinan, F. Scheinmann. 3-Alkyl-1-Alkynes Synthesis: 3-Ethyl-1-Hexyne . Organic Syntheses . 1978 . 58 . 1 .
3. 10.15227/orgsyn.068.0130. Norio Miyaura Akira Suzuki. Palladium-Catalyzed Reaction of 1-Alkenylboronates with Vinylic Halides: (1Z,3E)-1-Phenyl-1,3-Octadiene . Organic Syntheses . 1990 . 68 . 130 .
4. Hogsed. M. J.. Lindsey. R. V.. 1953-10-01. The Reaction of 1-Hexyne and Diethyl Fumarate. Journal of the American Chemical Society. 75. 19. 4846–4847. 10.1021/ja01115a517. 0002-7863.