Alcohols Phenols And Ethers Question 98

Question: Which of the following are intermediates in the reaction of excess of $ CH_3MgBr $ with $ C_6H_5COOC_2H_5 $ to make 2-phenyl - 2-propanol-

A. $ C_6H_5-\underset{CH_3}{\overset{OMgBr}{\mathop{\underset{|}{\overset{|}{\mathop{C}}}}}}-OCH_2CH_3 $ B. $ C_6H_5-\underset{{}}{\overset{O}{\mathop{\underset{{}}{\overset{||}{\mathop{C}}}}}}-CH_3 $ C. $ C_6H_5-\underset{CH_3}{\overset{OMgBr}{\mathop{\underset{|}{\overset{||}{\mathop{C}}}}}}-CH_3 $

Options:

A) A and B

B) A, B and C

C) A and C

D) B and C

Show Answer

Answer:

Correct Answer: B

Solution:

[b] $ C_6H_5-\overset{O}{\mathop{\overset{||}{\mathop{C}}}}-OC_2H_5+CH_3MgBr\xrightarrow{{}} $

$ \underset{(A)}{\mathop{C_6H_5-\underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{OMgBr}{\mathop{\overset{|}{\mathop{C}}}}}}}}-OC_2H_5}}\xrightarrow{{}}\underset{(B)}{\mathop{C_6H_5-\underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{O}{\mathop{\overset{||}{\mathop{C}}}}}}}}-C_2H_5OMgBr}} $

$ \underset{(C)}{\mathop{\xrightarrow{CH_3MgBr}C_6H_5-\underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{OMgBr}{\mathop{\overset{|}{\mathop{C}}}}}}}}-CH_3}}\xrightarrow{H_3{O^{+}}} $

$ \underset{{}}{\mathop{C_6H_5-\underset{CH_3}{\mathop{\underset{|}{\mathop{\overset{OH}{\mathop{\overset{|}{\mathop{C}}}}}}}}-CH_3}} $