Ass'N Tool (Pun Intended!)

Well, so we all know (or do we? Haha!) that the famous SN2 reaction proceeds via a 'backside' attack.

Yep, you got that right - when the nucleophile attacks an alkyl halide, it hits it right on its gluteus maximus (actually, I see it from another angle, but never mind).

And of course the age-old question: why? Why in particular, the 'backside'? Well, everything will be made clear with Molecular Orbital theory, so let us consider what the LUMO (Lowest Unoccupied Molecular Orbital) of a typical alkyl halide (in this case, chloromethane) looks like:


Notice the huge lobe on the 'backside' of the carbon atom? That's where the nucleophile attacks if if wants to bond to the carbon atom - by donating electrons into this antibonding orbital, the carbon-chlorine sigma bond effectively breaks, and a SN2 reaction ensues.

Ah well. I probably haven't explained in detail enough. But hey, I'm tired. :)

Recollection

I know I've asked this before, but it keeps coming back to me, again and again:

Does a proton possess orbitals?

If you say I'm silly, then consider the thousands of Chemists worldwide who speak of the hydrogen ion (H+) as having orbitals.

Isn't a hydrogen ion a proton?

But isn't a proton a free particle by itself?

Quantum mechanics is just plain weird, period. :)