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  •  » SN2 substitution reaction of crotyl bromide to give pent-3-enenitrile

#1 2010-12-05 13:26:44

orgopete
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SN2 substitution reaction of crotyl bromide to give pent-3-enenitrile

What is the major organic product of this reaction?
H3C-CH=CH-CH2-Br+ KCN -->

Will the substitution give trans or cis?

This should be a simple SN2 substitution reaction. No change should occur in the double bond. The double bond by virtue of it providing some electron withdrawing character to the carbon, will accelerate the substitution compared with butane. Some SN2i may also occur, that is an allylic substitution to give the 2-methylbut-3-enenitrile.
     http://www.curvedarrow.com/chem/ZZ40A57C27.jpg

Keywords, crotyl bromide, 1-bromo-2-butene, 1-bromobut-2-ene

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