A) \[{{(C{{H}_{3}})}_{2}}C(Cl)C{{H}_{2}}C{{H}_{3}}\]
B) \[{{(C{{H}_{3}})}_{2}}CHC{{H}_{2}}C{{H}_{2}}Cl\]
C) \[C{{H}_{3}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}C{{H}_{2}}X\]
D) Both (a) and (b)
Correct Answer: D
Solution :
Since, the compound gives 2-methyl butane, it must contain the following carbon skeleton. \[C-\overset{C}{\mathop{\overset{|}{\mathop{C}}\,}}\,-C-C\] Thus, the structure of chloride may be \[{{(C{{H}_{3}})}_{2}}C(Cl)C{{H}_{2}}C{{H}_{3}}\] or \[{{(C{{H}_{3}})}_{2}}CHC{{H}_{2}}C{{H}_{2}}Cl\] and the reactions are as follows \[{{(C{{H}_{3}})}_{2}}C(Cl)C{{H}_{2}}C{{H}_{3}}+Mg\xrightarrow{dry\,ether}\] \[{{(C{{H}_{3}})}_{2}}\underset{C}{\mathop{\underset{|}{\mathop{MgCl}}\,}}\,-C{{H}_{2}}C{{H}_{3}}\xrightarrow{{{C}_{2}}{{H}_{5}}OH}\] \[{{(C{{H}_{3}})}_{2}}CHC{{H}_{2}}C{{H}_{3}}\] \[{{(C{{H}_{3}})}_{2}}CHC{{H}_{2}}C{{H}_{2}}Cl+Mg\xrightarrow{dry\,ether}\] \[{{(C{{H}_{3}})}_{2}}CHC{{H}_{2}}MgCl\xrightarrow{{{C}_{2}}{{H}_{5}}OH}\] \[{{(C{{H}_{3}})}_{2}}CHC{{H}_{2}}C{{H}_{3}}\]
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