The acid shown is heated with methanol enriched in ^18O (CH3-18OH) and a catalytic amount of H2SO4. Which structure is the ester that forms?

MolSynapse / Question bank / Aldehydes, Ketones and Carboxylic Acids / Acidity order and derivative reactivity among drawn carboxylic acids

JEE Advanced levelSingle correct optionDifficulty 3 of 3co269

The acid shown is heated with methanol enriched in $^{18}$ O (CH3-18OH) and a catalytic amount of $H X_{2} SO X_{4}$ . Which structure is the ester that forms?

AStructure A
BStructure B
CStructure C
DStructure D

Answer: C

The drawn compound is benzoic acid. In Fischer esterification the alcohol oxygen attacks the protonated C=O, and water is lost from the acid side (acyl-oxygen cleavage). The labelled alcohol oxygen therefore ends up as the OR oxygen of methyl benzoate, and the label is not in the C=O oxygen.

Practice Aldehydes, Ketones and Carboxylic Acids More on Acidity order and derivative reactivity among drawn carboxylic acids

Previous questionNext question

The acid shown is heated with methanol enriched in 18O (CH3-18OH) and a catalytic amount of HX2​SOX4​. Which structure is the ester that forms?

Answer: C

More questions on Acidity order and derivative reactivity among drawn carboxylic acids

The acid shown is heated with methanol enriched in $^{18}$ O (CH3-18OH) and a catalytic amount of $H X_{2} SO X_{4}$ . Which structure is the ester that forms?