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Question
Explain the mechanism of esterification. Write the reactions involved in dehydration of 1o, 2o and 3o alcohols.
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Solution
The mechanism of esterification:
The carbonyl oxygen of the carboxylic acid is protonated. This increases the positive character of carbonyl carbon. The nucleophile (alcohol) attacks the carbonyl carbon. This is followed by intramolecular proton transfer and loss of water molecule. In the final step, deprotonation gives ester.
Dehydration of primary alcohol:
CH3−CH2−OH95%H2SO4−−−−−−−→443KCH2=CH2+H2O
Dehydration of secondary alcohol:
CH3−CH(OH)−CH360%H2SO4−−−−−−−→373KCH3−CH=CH2+H2O
Dehydration of tertiary alcohol:
CH3−CH(OH)(CH3)−CH3Al2O3−−−→423KCH3−C(CH3)=CH2+H2O
The carbonyl oxygen of the carboxylic acid is protonated. This increases the positive character of carbonyl carbon. The nucleophile (alcohol) attacks the carbonyl carbon. This is followed by intramolecular proton transfer and loss of water molecule. In the final step, deprotonation gives ester.
Dehydration of primary alcohol:
CH3−CH2−OH95%H2SO4−−−−−−−→443KCH2=CH2+H2O
Dehydration of secondary alcohol:
CH3−CH(OH)−CH360%H2SO4−−−−−−−→373KCH3−CH=CH2+H2O
Dehydration of tertiary alcohol:
CH3−CH(OH)(CH3)−CH3Al2O3−−−→423KCH3−C(CH3)=CH2+H2O
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