Nef synthesis

{{distinguish|Nef isocyanide reaction|Nef reaction}}

{{Reactionbox

| Name = Nef synthesis

| Type = Coupling reaction

| NamedAfter = John Ulric Nef

| Section3 = {{Reactionbox Identifiers

| RSC_ontology_id = 0000506

}}

}}

In organic chemistry, Nef synthesis is the addition of sodium acetylides to aldehydes and ketones to yield propargyl alcohols.{{cite journal|last1=Nef|first1=John Ulric|title=Ueber das Phenylacetylen, seine Salze und seine Halogensubstitutionsproducte|journal=Justus Liebigs Annalen der Chemie|date=1899|volume=308|issue=3|pages=264–328|doi=10.1002/jlac.18993080303|url=https://zenodo.org/record/1427517}}{{cite book|last1=Johnson|first1=A. W.|title=The Chemistry of the Acetylenic Compounds|date=1946|publisher=Arnold|location=London|page=11|edition=1st|isbn=978-0-598-99095-2 |url=https://books.google.com/books?id=e7E3AAAAMAAJ|accessdate=25 February 2016}}{{cite journal|last1=Hurd|first1=Charles D.|last2=McPhee|first2=Warren D.|title=Condensation of Acetylene with Acetone and Other Ketones|journal=Journal of the American Chemical Society|date=1947|volume=69|issue=2|pages=239–241|doi=10.1021/ja01194a018}}{{cite journal|last1=Oroshnik|first1=William|last2=Mebane|first2=Alexander D.|title=The Nef Reaction with α,β-Unsaturated Ketones|journal=Journal of the American Chemical Society|date=1949|volume=71|issue=6|pages=2062–2065|doi=10.1021/ja01174a048}}{{cite book|last1=Raphael|first1=Ralph Alexander|title=Acetylenic Compounds in Organic Synthesis|date=1955|publisher=Butterworths|location=London|page=10|edition=1st|url=http://babel.hathitrust.org/cgi/pt?id=mdp.39015064396958;view=1up;seq=1|accessdate=25 February 2016}}{{cite journal|last1=Coffman|first1=Donald D.|title=Dimethylethhynylcarbinol|journal=Organic Syntheses|date=1940|volume=40|page=20|doi=10.15227/orgsyn.020.0040}} It is named for John Ulric Nef, who discovered the reaction in 1899.

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This process is often erroneously referred to as the Nef reaction,{{cite book|last1=Viehe|first1=Heinz Günter|title=Chemistry of Acetylenes|url=https://archive.org/details/chemistryofacety0000vieh|url-access=registration|date=1969|publisher=Marcel Dekker, inc.|location=New York|pages=[https://archive.org/details/chemistryofacety0000vieh/page/207 207–241]|edition=1st|doi=10.1002/ange.19720840843}}{{cite book|authorlink1=Melville Wolfrom|last1=Wolfrom|first1=Melville L.|title=Biographical Memoirs|chapter=John Ulric Nef: 1862—1915|date=1960|publisher=National Academy of Sciences|location=Washington, DC|page=218|edition=1st|url=http://www.nasonline.org/publications/biographical-memoirs/memoir-pdfs/nef-john-u.pdf|accessdate=24 February 2016}}{{cite book|last1=Smith|first1=Michael B.|last2=March|first2=Jerry|title=March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure|chapter=Chapter 16. Addition to Carbon–Hetero Multiple Bonds|date=2007|publisher=John Wiley & Sons, Inc.|location=Hoboken, New Jersey|isbn=9780471720911|pages=1359–1360|edition=6th|doi=10.1002/9780470084960.ch16}} which is an unrelated chemical transformation discovered by the same chemist.