Chemistry Hydrocarbons ETEA 2016
PMDC Verified Question 51 of 65
Select meta directing group of the following?
A
\( -\text{OH} \)
B
\( -\text{NR}_2 \)
C
\( -\text{OR} \)
D
\( -\text{CN} \)
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

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

Meta-directing groups withdraw electron density from the benzene ring, typically via resonance, possessing an atom with a partial positive charge directly attached to the ring.

Solution:

  • The cyano group (\( -\text{C}\equiv\text{N} \)) consists of a carbon atom triple-bonded to a highly electronegative nitrogen.


  • The nitrogen pulls electron density, placing a partial positive charge on the carbon. This carbon subsequently withdraws electrons from the benzene ring through resonance.


  • This makes \( -\text{CN} \) a strong deactivating, meta-directing group.


Why other options are incorrect:

  • \( -\text{OH} \), \( -\text{NR}_2 \), and \( -\text{OR} \) all have atoms (O or N) directly attached to the ring containing lone pairs. These lone pairs are donated into the ring via resonance, rendering them activating, ortho/para directing groups.

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