[anya]

Hi
I need help with a synthesis problem.
I need to make 3 different alcohols from alcohols of 5 carbons or less.

Need to make 1-ethylcyclopentanol, 2-ethylcyclopentanol and 3 -ethylcyclopentanol

I synthesized first one through Grignard, and 2nd one thorugh hydroboration but I am stuck doing the third one. I am not sure how to put that ethyl group to the third position.

Thank you very much for the help.

[Donaldson Tan]

make cyclo-pentan-1,3-diol.

attack TsCl with one of the -OH to form -O-Ts

use a grignard to form an C=CH carboanion to attack the tosylated site.

reduce C=C with H2