Chemistry Carboxylic Acids MDCAT 2017
PMDC Verified Question 74 of 94
During esterification, the bond from alcohol that breaks is between:
A
Carbon and Oxygen
B
Carbon and carbon
C
Oxygen and hydrogen
D
None of these
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: Oxygen and hydrogen
Concept:

Through isotopic labeling experiments (using Oxygen-18), it is proven that during the Fischer esterification process, the carboxylic acid contributes the \(-\text{OH}\) group, while the alcohol contributes only the \(-\text{H}\) atom to form water.

Formula:

$$ \text{RCO-OH} + \text{H-OR}' \longrightarrow \text{RCO-OR}' + \text{H}_2\text{O} $$

Solution:

  • The nucleophilic oxygen of the alcohol attacks the electrophilic carbonyl carbon of the carboxylic acid.


  • To stabilize the resulting intermediate, the alcohol loses its proton (\( \text{H}^+ \)).


  • Therefore, the bond that breaks in the alcohol molecule is exclusively the O-H bond (Oxygen and Hydrogen).


Why other options are incorrect:

Breaking the C-O bond in alcohol would imply the alcohol provides the \(-\text{OH}\) group, which is factually incorrect for standard carboxylic acid esterification.

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