Homework Help: Organic Chemistry

Posted by Marissa on Wednesday, November 26, 2008 at 1:03pm.

How would you expect the following series of compounds to compare in behavior for SN1 vs SN2?
CH3CH=CHCH2Br
CH3CH2CH2Br
CH3C(-Br)=CHCH3

on the last one, Br is a substituent of the C and that C is double bonded to CHCH3

Please help! Even if someone could just help me get started on it, I am completely lost.

Organic Chemistry - DanH, Wednesday, November 26, 2008 at 4:18pm
Woops, sorry Marissa for the delay; just saw your question!

Remember, Sn1 reactions are based on the stability of the carbocations formed in the intermediate step. And Sn2 is favored if the carbocation formed is very unstable, thus it occurs in 1 step, without the intermediate carbocation. Do you know which of these 3 would form the most stable carbocation?

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