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Question 45 of 48

Q.The reaction of toluene with Cl2 in presence of Fe yields the major organic compound

(a) benzyl chloride (C6H5-CH2Cl)
(b) benzal chloride (C6H5-CHCl2)
(c) 4-chlorotoluene (para; ring bears CH3 and Cl at para positions)
(d) 3-chlorotoluene (meta; ring bears CH3 and Cl at meta positions)
West Bengal WbchseWest Bengal HS (WBCHSE) Board 2026MCQ· 1mImportance★★★★★
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Cl2 with Fe/FeCl3 gives electrophilic ring chlorination (not side-chain). The -CH3 group is ortho/para-directing and the less hindered para isomer, 4-chlorotoluene, is the major product. Correct option (c).

Reaction conditions decide the site:

  • Cl2 with Fe (or FeCl3, a Lewis acid) generates Cl+ for electrophilic aromatic substitution on the ring.
  • The methyl group is activating and ortho/para-directing, so chlorine enters ortho or para; because of less steric hindrance the para product, 4-chlorotoluene, is the major organic compound (some ortho, 2-chlorotoluene, also forms). …

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