Chemistry Carboxylic Acids NUMS 2024
PMDC Verified Question 18 of 94
Identify the following compound having shortest bond length:
A
Methyl amine
B
Formic acid
C
Formamide
D
Ethanol
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option B: Formic acid
Concept:

Bond length correlates with bond order; double bonds (\( \text{C=O} \)) are substantially shorter than single bonds (\( \text{C-O} \), \( \text{C-N} \)). Resonance can lengthen a double bond by giving it partial single-bond character.

Solution:

  • Methyl amine (\( \text{C-N} \)) and Ethanol (\( \text{C-O} \)) possess only single bonds, which are long.


  • Formamide (\( \text{H-CO-NH}_2 \)) contains a \( \text{C=O} \) bond, but the nitrogen's lone pair donates heavily into the carbonyl via resonance, significantly lengthening the \( \text{C=O} \) bond.


  • Formic acid (\( \text{H-COOH} \)) also has a \( \text{C=O} \) bond, but oxygen is much less willing to donate its lone pair via resonance than nitrogen. Therefore, the \( \text{C=O} \) retains more pure double-bond character, making it the shortest bond among the choices.


Why other options are incorrect:

Single bonds are inherently longer than double bonds. Nitrogen resonance in amides lengthens the carbonyl bond more than oxygen resonance in acids.

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