question_answer

\[0.44g\]of a monohydric alcohol when added to methyl magnesium iodide in ether liberates at S.T.P., \[112c{{m}^{3}}\]of methane. With PCC the same alcohol forms a carbonyl compound that answers silver mirror test. The monohydnc alcohol is

A)  \[C{{H}_{3}}-\underset{OH}{\mathop{\underset{|}{\mathop{C}}\,}}\,H-C{{H}_{2}}-C{{H}_{3}}\]

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

C)  \[C{{H}_{3}}-\underset{OH}{\mathop{\underset{|}{\mathop{C}}\,}}\,H-C{{H}_{2}}-C{{H}_{2}}-C{{H}_{3}}\]

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

Correct Answer: D

Solution :

: Mass of alcohol \[=\frac{0.44\times 22,400}{112}=88g\] Alcohol reacts with PCC to give a carbonyl compound which answers silver mirror test. Therefore, alcohol must be primary alcohol which on oxidation with PCC gives aldehyde; (carbonyl compound). Therefore, either or is correct. Out of these has the mass 88.