Editing Propyne (section)

==Organic chemistry==
Propyne is a convenient three-carbon building block for [[organic synthesis]]. Deprotonation with [[n-Butyllithium|''n''-butyllithium]] gives [[propynyllithium]]. This [[nucleophilic]] reagent adds to [[carbonyl]] groups, producing [[Alcohol (chemistry)|alcohol]]s and [[ester]]s.<ref>{{OrgSynth | author1 = Michael J. Taschner|author2=Terry Rosen|author3=Clayton H. Heathcock | title = Ethyl Isocrotonate | collvol = 7 | collvolpages = 226| year = 1990 | prep = CV7P0226}}</ref>  Whereas purified propyne is expensive, MAPP gas could be used to cheaply generate large amounts of the reagent.<ref>{{US patent reference | number = 5744071 | y = 1996 | m = 11 | d = 19 | inventor = Philip Franklin Sims, Anne Pautard-Cooper | title = Processes for preparing alkynyl ketones and precursors thereof }}</ref>

Propyne, along with [[2-butyne]], is also used to synthesize [[alkylated]] [[hydroquinone]]s in the [[total synthesis]] of [[vitamin E]].<ref name=Cyclization>{{cite journal|author1=Reppe, Walter |author2=Kutepow, N |author3=Magin, A |name-list-style=amp |title=Cyclization of Acetylenic Compounds|journal=Angewandte Chemie International Edition in English|year=1969|volume=8|issue=10|pages=727–733|doi=10.1002/anie.196907271}}</ref>

The chemical shift of an alkynyl proton and propargylic proton generally occur in the same region of the [[Proton nuclear magnetic resonance|<sup>1</sup>H NMR]] spectrum.  In propyne, these two signals have almost exactly the same chemical shifts, leading to overlap of the signals, and the <sup>1</sup>H NMR spectrum of propyne, when recorded in deuteriochloroform on a 300&nbsp;MHz instrument, consists of a single signal, a sharp singlet resonating at 1.8 ppm.<ref>{{Cite book|title=Organic chemistry|first1=Marc|last1=Loudon|first2=Jim|last2=Parise|others=Parise, Jim, 1978-|isbn=9781936221349|edition= Sixth|location=Greenwood Village, Colorado|publisher=W. H. Freeman|oclc=907161629|date = 2015-08-26}}</ref>