Formation of alkynes through double elimination of vicinal dibromides
Description: Sodium amide will convert 1,2-dihalides (“vicinal dihalides”) into alkynes through two consecutive elimination reactions.
This page is available to MOC Members only.
Sign up here for about 30 cents/ day!
Real-Life Examples:
Org. Synth. 1926, 6, 26
DOI Link:10.15227/orgsyn.006.0026
Click to Flip
Org. Synth. 1922, 2, 67
DOI Link:10.15227/orgsyn.002.0067
Click to Flip
Org. Synth. 1938, 18, 3
DOI Link: 10.15227/orgsyn.018.0003
Click to Flip
Org. Synth. 1932, 12, 60
DOI Link: 10.15227/orgsyn.012.0060
Click to Flip
Org. Synth. 1942, 22, 50
DOI Link: 10.15227/orgsyn.022.0050
Click to Flip
Org. Synth. 1958, 38, 70
DOI Link: 10.15227/orgsyn.038.0070
Click to Flip
Org. Synth. 1950, 30, 72
DOI Link: 10.15227/orgsyn.030.0072
Click to Flip
Org. Synth. 1957, 37, 77
DOI Link: 10.15227/orgsyn.037.0077
Click to Flip
Org. Synth. 1952, 32, 104
DOI Link: 10.15227/orgsyn.032.0104
Click to Flip
Org. Synth. 1979, 59, 10
DOI Link: 10.15227/orgsyn.059.0010
Click to Flip
My course taught us that we need three molar equivalents of NaNH2 for this reaction, as it prevents the formation of the alkynyl salt.
True, for terminal alkynes. Once the alkyne is formed, it can then be deprotonated by NaNH2 in solution. For practical purposes, three equivalents for the formation of terminal alkynes is best.
Would this also work with geminal dihalides?
Yes, it should.
Does this work the same way for Geminal Dihalides?
Yes it does!