alkyne multistep synthesis!!?

Question

CH3CH2CH2CH2OH -----> CH3CH2C[triple bond]CH

I need a multistep synthesis :) I'm a little lost on the terms still - I kinda get what I'm doing, but when it comes to what reagents remove what- I'M COMPLETELY LOST - so explainations on what it's doing to the compound would be great!!!!

thanks!

Answer 1

Here's another route to try, as direct reaction of sulfuric acid with primary alcohols often yields the corresponding ether instead of the desired alkene.

First convert the alcohol to the corresponding halide, then do a dehydrohalogenation followed by a 1,2 dibromination of the alkene and finish by reaction with sodium amide to get the desired alkyne

CH3CH2CH2CH2OH + SOCl2 (or PCl3) -->

CH3CH2CH2CH2Cl + hot EtOH/KOH --->

CH3CH2CH=CH2 + Br2 ---> CH3CH2CHBrCH2Br +

NaNH2 ---> CH3CH2CCH

Answer 2

CH3CH2CH2CH2-OH + H2SO4 ===> CH3CH2CH=CH2

+ 2Br2 ===> CH3CH2CHBr.CH2Br

+ (CH3)3CO-K+ ===> CH3CH2C[triplebond]CH

First, dehydrate the alcohol to an olefin. Next, brominate the olefin to a dibromide. Finally, a double elimination of HBr with a strong base.

Answer 3

CH3-CH2-CH2-CH2OH is Butyl alcohol. C4H9OH

It's dehydrated (-H2O) to form Butene. C4H8.
It's then Dehydrogenated (-H2) to give Butyne.

CH3-CH2-C≡CH...C4H6 Butyne.