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  4. Acetic acid reacts separately with the following alcohols. The rate of esterification is highest for

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Q. Acetic acid reacts separately with the following alcohols. The rate of esterification is highest for

CMC MedicalCMC Medical 2007

Solution:

As the hydrocarbon part (R) of the alcohol increases, the tetrahedral intermediate (I) formed during esterification becomes more and more crowded and hence the rate of esterification decreases accordingly. Thus, the smallest alcohol, i.e., $ C{{H}_{3}}OH $ reacts at the fastest rate $ C{{H}_{3}}-\overset{O}{\mathop{\overset{\mathbf{||}}{\mathop{C}}\,}}\,-OH\xrightarrow{{{H}^{+}}}C{{H}_{3}}-\overset{{}^{+}OH}{\mathop{\overset{\mathbf{||}}{\mathop{C}}\,}}\,-OH\xrightarrow{ROH} $ $ \underset{\text{tetrahedral}\,\text{intermediate}\,\text{(i)}}{\mathop{\left[ {{H}_{3}}C\,\,\,\underset{OR}{\overset{OH}{\mathop{\overset{\mathbf{|}}{\mathop{\overset{C}{\mathop{|}}\,}}\,}}}\,\,\,\,\,OH \right]}}\,\xrightarrow{-{{H}_{2}}O}\underset{\text{ester}}{\mathop{C{{H}_{3}}-\overset{O}{\mathop{\overset{\mathbf{||}}{\mathop{C}}\,}}\,-OR}}\, $