Alcohols Phenols And Ethers Question 290

Question: Glycerol heated with oxalic acid at $ 110^{o}C $ to form

[CPMT 1986, 90, 91, 97; JIPMER 1997]

Options:

A) Formic acid

B) Oxalic acid

C) Allyl alcohol

D) Glycerol trioxalate

Show Answer

Answer:

Correct Answer: A

Solution:

$ \underset{CH_2-OH}{\overset{CH_2-OH}{\mathop{\underset{|}{\overset{|}{\mathop{CH}}}-OH}}}+\begin{matrix} COOH \\ \overset{|}{\mathop{C}}OOH \\ \end{matrix}\underset{-H_2O}{\mathop{\xrightarrow{110^{o}C}}}\underset{Glycerol\text{mono-oxolate}}{\mathop{\underset{CH_2-OH}{\overset{CH_2-O-CO-COOH}{\mathop{\underset{|}{\overset{|}{\mathop{CH}}}-OH\xrightarrow[-CO_2]{}}}}}} $

$ \underset{Glycerol\text{mono-formate}}{\mathop{\underset{CH_2-OH}{\overset{CH_2-O-CO-H}{\mathop{\underset{|}{\overset{|}{\mathop{CH}}}-OH}}}}}\xrightarrow{Hydrolysis}\underset{Formicacid}{\mathop{\underset{HCOOH}{\mathop{\underset{+}{\mathop{\underset{CH_2-OH}{\overset{CH_2-OH}{\mathop{\underset{|}{\overset{|}{\mathop{CH}}}-OH}}}}}}}}} $