Convert ethyl alcohol to vinyl acetate

[NEILS BOHR]

Homework Statement

Convert ethyl alcohol to vinyl acetate ( in not more than 6 steps)..

Homework Equations

The Attempt at a Solution

this is wat i tried:
first added conc. H2SO4 at 120 degrees , ethene is formed , then added Br2 in CCl4 , 1 2 dibromoethane is obtained ...then added NaNH2 and ethyne is formed...

what to do next??any idea??

 

[Trave11er]

Ethyne can be converted to vinyl alcohol if treated with H2SO4, H2O and Hg2+ salt (This is a general reaction that allows to obtain aldehydes/ketones from alkynes (agrees with Markovnikov's rule)). But in reality acetaldehyde would be obtained instead from ethyne and almost none of it will isomerase to vinyl alcohol. So I strongly douubt if you can obtain a vinyl ester from the acetadehyde. It is probably better to first obtain something like the required ester and then get the double bond somehow.

 

[NEILS BOHR]

hmmm
but i m still confused...not gettin the rite method
more replies pleasezz...