Chemistry Hydrocarbons MDCAT 2017
PMDC Verified Question 46 of 65
Which of the following species are 3,5(meta) directing groups when second group is introduced into the benzene ring?
I = \( -\text{NH}_2 \)
II = \( -\text{CHO} \)
III = \( -\text{COOH} \)
IV = \( -\text{CH}_3 \)
A
II, III and IV
B
I and IV
C
II and III
D
I, II and IV
Tap any option to test your recall and reveal the step-by-step Propolis autopsy.

Propolis Cognitive Error Autopsy

Official Correct Choice:
Option C: II and III
Concept:

Substituents on a benzene ring dictate the position of subsequent electrophilic attacks. Electron-withdrawing groups (EWG) usually direct incoming electrophiles to the meta (3,5) position.

Solution:

  • Group I (\( -\text{NH}_2 \)) and Group IV (\( -\text{CH}_3 \)) are electron-donating groups (EDG). They activate the ring and are ortho/para directing.


  • Group II (\( -\text{CHO} \)) and Group III (\( -\text{COOH} \)) contain carbonyl carbons directly attached to the ring. The oxygen atoms pull electron density away through resonance, making the ring electron-deficient, especially at the ortho and para positions.


  • Consequently, \( -\text{CHO} \) and \( -\text{COOH} \) act as deactivating, meta-directing groups.


Why other options are incorrect:

  • Any option including I or IV is incorrect because amines and alkyl groups are ortho/para directors.

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