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Topic: Alkylation  (Read 3418 times)

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dexangeles

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Alkylation
« on: February 22, 2005, 09:41:56 PM »
I know that Sodium acetylide would easily react via Substitution with methyl or primary halides, but...

would sodium acetylide react with an alkenyl halide (eg. H2C=CHBR) via Substitution also? Or would it be an E reaction?  I'm not sure if a carbon double bonded to another carbon would still be considered primary.

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Re:Alkylation
« Reply #1 on: February 23, 2005, 01:54:03 PM »
No, substitution reactions on vinyl halides don't work.  The carbon halogen bond is stronger because it involves an sp2 hybrid on carbon.  Also there is a large steric component to the reaction due to the substituents at the allylic position.

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