Convert ethyl alcohol to vinyl acetate

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SUMMARY

The conversion of ethyl alcohol to vinyl acetate involves several key steps, starting with the addition of concentrated H2SO4 at 120 degrees Celsius to form ethene. Following this, bromination using Br2 in CCl4 yields 1,2-dibromoethane. The next step involves the use of NaNH2 to produce ethyne. However, converting ethyne to vinyl alcohol using H2SO4, H2O, and Hg2+ salt typically results in acetaldehyde rather than vinyl alcohol, complicating the synthesis of vinyl acetate. A more effective approach may involve synthesizing the required ester directly before introducing a double bond.

PREREQUISITES
  • Understanding of organic reaction mechanisms, particularly electrophilic addition and elimination reactions.
  • Familiarity with the properties and reactions of alkenes and alkynes.
  • Knowledge of Markovnikov's rule and its application in organic synthesis.
  • Experience with reagents such as concentrated sulfuric acid (H2SO4) and sodium amide (NaNH2).
NEXT STEPS
  • Research the synthesis of vinyl acetate from acetic acid and ethylene using acid-catalyzed esterification.
  • Study the mechanism of alkene formation from alcohols through dehydration reactions.
  • Explore the conversion of acetaldehyde to vinyl acetate and the challenges involved.
  • Investigate alternative methods for synthesizing vinyl alcohol and its derivatives.
USEFUL FOR

Chemistry students, organic chemists, and anyone involved in synthetic organic chemistry looking to understand the conversion processes of alcohols to esters.

NEILS BOHR
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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??:confused:
 
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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.
 


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

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