Match each of the compounds in Column I with its characteristic reaction(s) in Column II.
| Column I | Column II |
|---|---|
| (A) | (p) Reduction with Pd-C/H₂ |
| (B) | (q) Reduction with SnCl₂/HCl |
| (C) | (r) Development of foul smell on treatment with chloroform and alcoholic KOH |
| (D) | (s) Reduction with diisobutylaluminium hydride (DIBAL-H) |
| (t) Alkaline hydrolysis |
Answer: A → I, A → II, A → IV, A → V, B → IV, B → V, C → I, D → III
Solution
(A) CH₃CH₂CH₂CN (nitrile):
(B) CH₃CH₂OCOCH₃ (ester):
(C) CH₃-CH=CH-CH₂OH (allylic alcohol):
(D) CH₃CH₂CH₂CH₂NH₂ (primary amine):
Matches: A→p,q,s,t; B→s,t; C→p; D→r
- Can be reduced with Pd-C/H₂ to primary amine (p)
- Can be reduced with SnCl₂/HCl to aldehyde (q)
- Can be reduced with DIBAL-H to aldehyde (s)
- Undergoes alkaline hydrolysis to carboxylic acid (t)
(B) CH₃CH₂OCOCH₃ (ester):
- Can be reduced with DIBAL-H to alcohols (s)
- Undergoes alkaline hydrolysis (saponification) (t)
(C) CH₃-CH=CH-CH₂OH (allylic alcohol):
- The C=C double bond can be reduced with Pd-C/H₂ (p)
(D) CH₃CH₂CH₂CH₂NH₂ (primary amine):
- Gives carbylamine test (foul smell) with CHCl₃ and alcoholic KOH (r)
Matches: A→p,q,s,t; B→s,t; C→p; D→r
JEE Advanced · 2009 · 12 Apr 2009 · Paper 1 · Match the columns