Chemistry Hydrocarbons MDCAT 2017
PMDC Verified Question 49 of 65
Among the following, which one has electron withdrawing effect:
A
\( -\text{NH}_2 \)
B
\( -\text{N}(\text{CH}_3)_2 \)
C
\( -\text{I} \)
D
\( -\text{CHO} \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option D: \( -\text{CHO} \)
Concept:

Electron-withdrawing groups (EWG) usually possess atoms with a partial or full positive charge directly bonded to the ring, often due to multiple bonds with more electronegative atoms (like oxygen).

Solution:

  • The formyl group (\( -\text{CHO} \)) features a carbon atom double-bonded to a highly electronegative oxygen atom.


  • The oxygen pulls electron density away from the carbon, leaving it with a partial positive charge. This carbon, in turn, withdraws pi electron density from the benzene ring via resonance.


  • Hence, \( -\text{CHO} \) is a strong electron-withdrawing and ring-deactivating group.


Why other options are incorrect:

  • \( -\text{NH}_2 \) and \( -\text{N}(\text{CH}_3)_2 \) possess nitrogen atoms with a lone pair that can be donated into the ring via resonance, making them electron-donating groups (EDG).


  • Iodine (\( -\text{I} \)) withdraws electrons inductively but donates them via resonance. It is considered weakly deactivating but ortho/para directing. However, compared to \( -\text{CHO} \), the aldehyde group is fundamentally the definitive EWG via strong resonance.

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