Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in Column II.
Column I
(A) (see structure)
(B) (see structure)
(C) (see structure)
(D) (see structure)
Column II
(p) Nucleophilic substitution
(q) Elimination
(r) Nucleophilic addition
(s) Esterification with acetic anhydride
(t) DehydrogenationABCD
Answer: A → I, A → II, A → V, B → I, B → IV, B → V, C → III, C → IV, D → I
Solution
(A) The benzofuran derivative with Br can undergo nucleophilic substitution (Br leaving), elimination (to form double bond), and dehydrogenation.
(B) Benzyl alcohol can undergo nucleophilic substitution (OH as leaving group after activation), esterification with acetic anhydride, and dehydrogenation to benzaldehyde.
(C) Salicylaldehyde has both aldehyde (nucleophilic addition) and phenolic OH (esterification).
(D) o-Bromonitrobenzene can undergo nucleophilic aromatic substitution due to activation by the nitro group.
JEE Advanced · 2009 · 12 Apr 2009 · Paper 2 · Match the columns
