NEET2007ChemistryAlcohols Phenols and EthersActual
( CH ₃ OC ₂ H ₅ ) and ( ( CH ₃ )₃ C - OCH ₃ ) are treated with hydroiodic acid. The fragments after reactions obtained are
Options
- A( CH ₃ I + HOC ₂ H ₅ ; ( CH ₃ )₃ C - I + HOCH ₃ )
- B( CH ₃ OH + C ₂ H ₅ I ; ( CH ₃ )₃ Cl + HOCH ₃ )
- C( CH ₃ OH + C ₂ H ₅ ; ( CH ₃ )₃ C - OH + CH ₃ I )
- D( CH ₃ I + HOC ₂ H ₅ ; CH ₃ I + ( CH ₃ )₃ C - OH ).
Correct answer
A. ( CH ₃ I + HOC ₂ H ₅ ; ( CH ₃ )₃ C - I + HOCH ₃ )
Step-by-step solution
When mixed ethers are used, the alkyl iodide produced depends on the nature of alkyl groups. If one group is Me and the other a pri- or sec-alkyl group, then methyl iodide is produced. Here reaction occurs via ( S _ N 2 ) mechanism and because of the steric effect of the larger group, ( I ⁻ )attacks the smaller (Me) group. ( CH ₃ OC ₂ H ₅+ HI CH ₃ I + C ₂ H ₅ OH ) When the substrate is a methyl (t )-alkyl ether, the products are (t-R I ) and ( MeOH ). Here reaction occurs by ( S _ N 1 ) mechanism and formation of p