Reactions of Alkynes

You may use these summaries and problems but you may NOT download them for use at another site, nor may you charge for access to them. Copyright Linda M. Sweeting 1997

The following example reactions are organized by type, with references to text chapters. Links within these summaries (which may show up as boxes around reagents) will provide further information about the reagents and their other reactions. Return to Graphical Reaction Summary menu for other functional group choices or to synthesis of alkynes.
Most reactions are the same as those of alkenes, except that two moles of reagent can be and usually is added.

Simple Additions


Mechanism!
McMurry 8.4, Fessenden 10.6, Schmid 9.6A

Mechanism! Rearrangement of the enol.
McMurry 8.5, Fessenden 10.7, Schmid 9.7A
+ H2O
The enol is formed and rearranges to the ketone, which is in turn reduced by the sodium borohydride; sodium borohydride is almost always used in excess because the hydrides react with air and water, making the number of moles uncertain.
McMurry 8.5, 17.15, 19.8, Fessenden 10.8, Schmid 9.7A

See alkene reactions for details.
McMurry 8.5, Fessenden 10.9, Schmid 9.7B

Reduction


Stereospecific! Surface reaction, complete reduction usually occurs
McMurry 8.6, 8.7, Fessenden 10.12, Schmid 9.8

Stereospecific!
McMurry 8.6, Fessenden 10.9, Schmid 9.8

Stereospecific!
McMurry 8.6, Fessenden 10.12, Schmid 9.8

Stereospecific!
McMurry 8.6, Fessenden 10.12B, Schmid 9.8

Oxidation


McMurry 8.4, Fessenden 10.5, Schmid 9.6B

As Weak Acids


+
SN2 reaction, stereospecific if halide is secondary
McMurry 8.6, 8.8, 8.9, Fessenden 10.4, Schmid 9.10
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Last update Feb. 10, 1999