Alcohols Phenols And Ethers Question 92

Question: The product of the following reaction,

Options:

A) $ CH_3-\underset{CH_3}{\overset{CH_3}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}}}}-\underset{OH}{\mathop{\underset{|}{\mathop{C}}}}H-CH_3 $

B) $ CH_3-\underset{CH_3}{\overset{CH_3}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}}}}-\underset{{}}{\mathop{\underset{{}}{\mathop{C}}}}H_2-CH_2OH $

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

D) $ HOCH_2-\underset{CH_3}{\overset{CH_3}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}}}}-\underset{{}}{\mathop{\underset{{}}{\mathop{C}}}}H_2-CH_3 $

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Answer:

Correct Answer: A

Solution:

[a] Recall that oxymercuratoin-reduction of alkenes lead to hydration in Markovnikov’s way. Thus $ {{(CH_3)}_3}CCH=CH_2\xrightarrow[(ii)NaBH_4]{(i)Hg{{(OAc)}_2}.H_2O}{{(CH_3)}_3}C\overset{OH}{\mathop{\overset{|}{\mathop{C}}}}HCH_3 $