Synthesis of Alkenes

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 reactions of alkenes.

By elimination from alcohols: Dehydration

+
Mechanism!; SN1 and E1; other reagents: HCl, HI
McMurry 5.1, 7.1, 11.10, 11.16, 11.19, 17.7, Fessenden 7.4-7.6, Schmid 11.17, 12.10, 12.11, 12.16

Elimination

+ H2O
Mechanism!; E1
McMurry 7.1, 11.10, Fessenden 7.6

By elimination from alkyl halides: Dehydrohalogenation


Mechanism! E2, Stereospecific
McMurry 11.12, 11.15, Fessenden 5.7-5.8, Schmid 12.12 - 12.15

By reduction


Stereospecific!
McMurry 8.5, Fessenden 10.9, Schmid 9.8

Stereospecific! For other reagents, click on the arrow above.
McMurry 6.7, 8.6, 8.10, Fessenden 10.12B, Schmid 9.8

Stereospecific!
McMurry 8.6, Fessenden 10.12B, Schmid 9.8


The Wittig reaction; works best with less substituted halides, aldehydes and ketones.
Fessenden 13.4D, Schmid 14.16, 14.17

Miscellanea

+
Diels Alder Reaction.
Stereospecific!
This is a reaction of the alkene and diene, not the C=O; it works best when the alkene is electron-deficient, so the C=O's function is to withdraw electrons
McMurry 14.8, 14.9, Fessenden 16.3, Schmid 19.12 (NOT 19.10 and 19.11)
Diene synthesis can be accomplished by all of the reactions above (except the Diels-Alder); where the reaction provides a choice, at equilibrium the conjugated (1,3) diene is more stable than the unconjugated diene or the alkyne.
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Last update Nov. 1, 1998