Alcohols Phenols And Ethers Question 249

Question: When glycerol is heated with $ KHSO_4 $ it gives

[CPMT 1974, 85; MP PMT 1988, 90, 91, 92, 94; MP PET 1988, 92]

Options:

A) $ CH_2=CH-CH_3 $

B) $ CH_2=CH-CH_2OH $

C) $ CH_2=CH-CHO $

D) $ CH_2=C=CH_2 $

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Answer:

Correct Answer: C

Solution:

$ \underset{Glycerol}{\mathop{\underset{\underset{OH}{\mathop{H-\underset{|}{\mathop{C}}-H}}}{\overset{H-\overset{H}{\mathop{\overset{|}{\mathop{C}}}}-OH}{\mathop{HO-\underset{|}{\overset{|}{\mathop{C}}}-H}}}}}\xrightarrow{KHSO_4}\underset{Unstable}{\mathop{\overset{\overset{H-\overset{\overset{H}{\mathop{|}}}{\mathop{C}}}{\mathop{||}}}{\mathop{\underset{\underset{\underset{OH}{\mathop{\underset{|}{\mathop{C}}-H}}}{\mathop{||}}}{\mathop{C}}}}}}\xrightarrow{{}} $

$ \overset{\overset{H-\overset{\overset{H}{\mathop{|}}}{\mathop{C}}}{\mathop{||}}}{\mathop{\underset{\underset{\underset{\underset{O}{\mathop{||}}}{\mathop{C}}-H}{\mathop{||}}}{\mathop{C-H}}}} $ or $ \underset{Acrolein}{\mathop{\underset{\underset{CHO}{\mathop{|}}}{\overset{\overset{CH_2}{\mathop{||}}}{\mathop{CH}}}}} $