Ethers
- Consider the following reaction :C_6H_5-CH_2-O-C_6H_5 [Δ]HI A + B (benzyl phenyl ether)Identify products A and B. Answer: 4. A = C ₆ H ₅ -CH ₂ I and B = C ₆ H ₅ -OH Key idea: HI cleaves an aryl alkyl ether at the alkyl-oxygen bond, because the aryl C-O b... 1
- Anisole on cleavage with HI gives : Answer: 1. Phenol (C ₆ H ₅ OH) + CH ₃ I Aryl alkyl ethers are cleaved by HI at the alkyl-oxygen bond. The ether oxygen is protonated, then I... 1
- The compound that is most difficult to protonate is : Answer: 4. Ph-O-H Protonation occurs on the oxygen lone pair; the more available the lone pair, the easier it is to protonate. H₂O , CH₃OH ,... 1
- The heating of phenyl-methyl ethers with HI produces. Answer: 2. phenol Key idea: HI cleaves an aryl alkyl ether at the alkyl-oxygen bond. C₆H₅OCH₃ + HI → C₆H₅OH + CH₃I . The oxygen is protonate... 1
- The reaction[cyclopentanol, then NaH giving sodium cyclopentoxide, then Me-I giving methyl cyclopentyl ether; scheme shown in figure]can be classified as : Answer: 1. Williamson ether synthesis reaction Key idea: an alcohol is converted by a strong base (NaH) into an alkoxide, which then attacks... 1