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  4. Tertiary alcohols (3° ) having at least four carbon atoms upon drastic oxidation yield carboxylic acid with

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Q. Tertiary alcohols $ (3{}^\circ ) $ having at least four carbon atoms upon drastic oxidation yield carboxylic acid with

CMC MedicalCMC Medical 2010

Solution:

A $ 3{}^\circ $ alcohol is very difficult to oxidised because they dont have carbon bearing $ -H $ and $ -OH $ both the groups. However, when treated under drastic conditions, cleavage of $ C-C $ bond takes place. They form mixture of ketone and carboxylic acid contains two carbon atom lesser than the starting alcohol. $ \underset{t-butyl\,alcohol}{\mathop{C{{H}_{3}}-\underset{C{{H}_{3}}}{\overset{C{{H}_{3}}}{\mathop{\underset{\mathbf{|}}{\overset{\mathbf{|}}{\mathop{C}}}\,}}}\,-OH}}\,\xrightarrow[(Strong\,condition)]{4[O]}\underset{\begin{smallmatrix} \,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,\,acetone \\ (one\,\,carbon\,\,atom\,\,less) \end{smallmatrix}}{\mathop{C{{H}_{3}}-\overset{C{{H}_{3}}}{\mathop{\overset{\mathbf{|}}{\mathop{C}}\,}}\,=O}}\, $ $ \xrightarrow[(strong\,condition)]{4\,[O]}\underset{two\,\,carbon\,\,atoms\,less}{\mathop{C{{H}_{3}}COOH}}\,+C{{O}_{2}}+{{H}_{2}}O $