Match each of the compounds given in Column I with the reaction(s), that they can undergo, given in Column II.
← IIT-JEE 2009 · Paper 2
ChemistryMatrix match+8Question 11 of 57
IIT-JEE 2009 · Paper 2, Chemistry question 11
Column I
- A
- B
- C
- D
Column II
- PNucleophilic substitution
- QElimination
- RNucleophilic addition
- SEsterification with acetic anhydride
- TDehydrogenation
| P | Q | R | S | T | |
|---|---|---|---|---|---|
| A | |||||
| B | |||||
| C | |||||
| D |
Answer and worked solution
Official answer: A → P, Q, T; B → P, S, T; C → R, S; D → P
- A, 3-bromo-2,3-dihydrobenzofuran: a secondary benzylic bromide, so it undergoes nucleophilic substitution and elimination; loss of HBr gives the aromatic benzofuran, which the key also counts as dehydrogenation. → P, Q, T.
- B, benzyl alcohol: substitution of OH (e.g. by halide), acetylation with acetic anhydride, and dehydrogenation (over hot Cu) to benzaldehyde. → P, S, T.
- C, salicylaldehyde: the CHO undergoes nucleophilic addition and the phenolic OH is acetylated. → R, S.
- D, 1-bromo-2-nitrobenzene: the ortho nitro group activates the ring for nucleophilic aromatic substitution of Br. → P.
Answer: A → P, Q, T; B → P, S, T; C → R, S; D → P