[oliverT]

Hello everyone,

I am currently working on a minor essay in which I am investigating the effect of the length of the carbon chain in alcohols on their rate of reaction with sodium (Na). However, as I am receiving little support from my teacher in this area, I am somewhat confused as to the type of reaction the occurs between sodium and the alcohols, as well as the exact way in which this proceeds, and would therefore very much appreciate any advice in the matter. I am aware that a shorter carbon chain will incur a faster rate of reaction, but am uncertain exactly why this is the case. My initial though goes to an increased polarity and thus a weaker bond with the hydroxyl leaving-group; however, I may indeed be completely wrong.

Any input whatsoever is utterly appreciated. Thanks in advance.

[JGK]

Check out the "Inductive Effect".

The OH group of the alcohol has a I+ effect causing it to act like an acid.

The alkyl group has an I- effect (increasing with chain length) "pushing" electrons towards the OH group and reducing the +ve charge around the OH group and therefore its relative acidity