JEE Main & Advanced Chemistry Alcohols, Phenols and Ethers / एल्कोहॉल, फीनॉल तथा ईथर Question Bank Properties of alcohol Phenol and Ethers

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    A substance \[{{C}_{4}}{{H}_{10}}O\] yields on oxidation a compound \[{{C}_{4}}{{H}_{8}}O\] which gives an oxime and a positive iodoform test. The original substance on treatment with conc. \[{{H}_{2}}S{{O}_{4}}\] gives \[{{C}_{4}}{{H}_{8}}\]. The structure of the compound is            [SCRA 2000]

    A)                 \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}OH\]

    B)                 \[C{{H}_{3}}CH(OH)C{{H}_{2}}C{{H}_{3}}\]

    C)                 \[{{(C{{H}_{3}})}_{3}}COH\]

    D)                 \[C{{H}_{3}}C{{H}_{2}}-O-C{{H}_{2}}C{{H}_{3}}\]

    Correct Answer: B

    Solution :

    \[C{{H}_{3}}CH(OH)C{{H}_{2}}C{{H}_{3}}\xrightarrow{\text{Conc}\text{.}\,{{H}_{2}}S{{O}_{4}}}\]\[\underset{({{C}_{4}}{{H}_{8}})}{\mathop{C{{H}_{3}}CH=CHC{{H}_{3}}}}\,\]            \[\underset{2-\text{Butanol}}{\mathop{C{{H}_{3}}CHOHC{{H}_{2}}C{{H}_{3}}}}\,\xrightarrow{[O]}\underset{\text{Butanone}}{\mathop{C{{H}_{3}}COC{{H}_{2}}C{{H}_{3}}}}\,\] Butanone gives both an oxime and positive iodoform test, therefore, the original compound is 2-butanol.


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