Hydrocarbons Question 417

Question: The product of following reaction is $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{CH_3}{\mathop{\overset{|}{\mathop{CH_3-C-CH=CH_2}}}}}}}}\underset{\text{(ii) }NaBH_4}{\mathop{\xrightarrow{(i)Hg{{(OAc)}_2};H_2O}}} $ [MP PMT 1986; MP PET 1997]

Options:

A) $ \underset{CH_3OH}{\mathop{\underset{||}{\mathop{\overset{CH_2}{\mathop{\overset{|}{\mathop{CH_3-C-CH-CH_2}}}}}}}} $

B) $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{CH_3}{\mathop{\overset{|}{\mathop{CH_3-C-CH_2-CH_2OH}}}}}}}} $

C) $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{OHCH_3}{\mathop{\overset{||}{\mathop{CH_3-C-CH-CH_3}}}}}}}} $

D) $ \underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{CH_3}{\mathop{\overset{|}{\mathop{HOCH_2-C-CH_2-CH_2}}}}}}}} $

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Answer:

Correct Answer: A

Solution:

$ CH_3-\underset{\underset{CH_3}{\mathop{|}}}{\overset{\overset{CH_3}{\mathop{|}}}{\mathop{C-C}}}H=CH_2\underset{ii)NaBH_4}{\mathop{\xrightarrow{I)Hg{{(OAc)}_2};H_2O}}} $

$ CH_3-\underset{\underset{CH_3}{\mathop{|}}}{\overset{\overset{CH_3}{\mathop{|}}}{\mathop{C-}}}\underset{\underset{OH}{\mathop{|}}}{\mathop{CH}}-CH_3 $