A) \[C{{H}_{3}}CH(OH)C{{H}_{3}}\]
B) \[CH{{ }_{3}}C{{H}_{2}}CH(OH)C{{H}_{3}}\]
C) \[C{{H}_{3}}OH\]
D) \[C{{H}_{3}}C{{H}_{2}}OH\]
Correct Answer: C
Solution :
An organic compound form yellow precipitate of iodoform with lo in presence of alkali, if it has\[C{{H}_{3}}CO\]group directly or it has\[C{{H}_{3}}-\underset{\begin{smallmatrix} | \\ OH \end{smallmatrix}}{\overset{\begin{smallmatrix} H \\ | \end{smallmatrix}}{\mathop{C}}}\,\]group [a] \[C{{H}_{3}}CH(OH)C{{H}_{3}}+{{I}_{2}}\xrightarrow[{}]{NaOH}C{{H}_{3}}COC{{H}_{3}}\] \[+2HI+3NaI+C{{H}_{3}}COONa+3{{H}_{2}}O\] \[C{{H}_{3}}COC{{H}_{3}}+3{{I}_{2}}+4NaOH\xrightarrow[{}]{{}}\underset{\begin{smallmatrix} Yellow \\ ppt. \end{smallmatrix}}{\mathop{CH{{I}_{3}}}}\,\downarrow \] \[+3NaI+C{{H}_{3}}COONa+3{{H}_{2}}O\] [b] \[C{{H}_{3}}-C{{H}_{2}}CH(OH)C{{H}_{3}}+{{I}_{2}}\xrightarrow[{}]{{}}\] \[\underset{Ethyl\text{ }methyl\text{ }ketone}{\mathop{C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix} || \\ O \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}}+2HI}}\,\] It gives iodoform test. \[C{{H}_{3}}-C{{H}_{2}}-\underset{\begin{smallmatrix} || \\ O \end{smallmatrix}}{\mathop{C}}\,-C{{H}_{3}}+3{{I}_{2}}+4NaOH\to \] \[\underset{Yellow\text{ }ppt.}{\mathop{CH{{I}_{3}}\downarrow }}\,+3NaI+C{{H}_{3}}C{{H}_{2}}COONa+3{{H}_{2}}O\] [c] \[C{{H}_{3}}OH+{{I}_{2}}\xrightarrow[{}]{{}}HCHO+2HI\] It does not have methyl ketonic group, so it does not give yellow ppt. with\[{{I}_{2}}\]in presence of alkali. [d] \[C{{H}_{3}}C{{H}_{2}}OH+{{I}_{2}}\xrightarrow[{}]{{}}C{{H}_{3}}-\underset{\begin{smallmatrix} || \\ O \end{smallmatrix}}{\mathop{C}}\,+H+2HI\] It gives iodoform test. \[C{{H}_{3}}-\underset{\begin{smallmatrix} || \\ O \end{smallmatrix}}{\mathop{C}}\,-H+3{{I}_{2}}+4NaOH\xrightarrow[{}]{{}}\underset{\begin{smallmatrix} Yellow \\ ppt. \end{smallmatrix}}{\mathop{CH{{I}_{3}}}}\,\] \[+HCOONa+3NaI+2{{H}_{2}}O\]
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