Question

How do you alkylate an alcohol?

Answer 1

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'CH_2OH + [O]rarrR'C(=O)H`

`R'C(=O)H + R^(-)Li^(+)rarrR'CH(-O^(-)Li^+)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.