[Suprachiasmatic Nucleus]

Hi, is there a method in which for a secondary carbon (which I believe can follow all four mechanisms) that the mechanism can be determined by the base/nucleophile strength?

I.E:

Secondary Carbon + Strong Base = Sn1 for instance - I'm not sure if that is even right, sigh.

Thanks for any help. :-)

[Mitsunobo]

I don't think the mechanism will be as straightforward as primary or tertiary carbon. It will be a combination of a lot of factor. The nucleophilicity of base ( smaller base are good nucleophiles that promotes SN2 reactions while bulkier bases promotes elimination). The solvents (polar protic solvents promote SN1 due to stabilizing effects of H-bonding while polar aprotic solvents promotes SN2 reactions). Having said this, it is still very difficult to predict the mechanism in which a secondary carbon will undergo.

[azmanam]

start here:
http://www.cem.msu.edu/~reusch/VirtualText/alhalrx3.htm#hal9
http://www.chem.uky.edu/courses/che230/RBG/handouts/drawSnE.HTML
http://www.chem.uky.edu/courses/che230/RBG/handouts/SNorE/SNorE_print.HTML