# How do you alkylate an alcohol?

Mar 15, 2017

Oxidize the alcohol to the carbonyl, and then treat this with a carbanion..........

#### Explanation:

Or, deprotonate the alcohol, and then use this alkoxide to act on an alkyl halide to form an alkyl halide.

And thus (with a primary alcohol):

$R ' C {H}_{2} O H + \left[O\right] \rightarrow R ' C \left(= O\right) H$

$R ' C \left(= O\right) H + {R}^{-} L {i}^{+} \rightarrow R ' C H \left(- {O}^{-} L {i}^{+}\right) R$

We get a secondary alkoxide..........

Alternatively, we could deprotonate the alcohol, and then treat this alkoxide with an alkyl halide to give an ether.

R'CH_2OH + n-Bu^(-)Li^(+)rarrR'CH_2O^(-)""^(+)Li +n-BuHuarr

R'CH_2O^(-)""^(+)Li +RXrarrR'CH_2OR +LiXdarr

This question was unanswered for so long because of this ambiguity.