A mixed ether (P), when heated with excess of hot concentrated hydrogen iodide produces two different alkyl iodides which when treated with aq. NaOH give compounds (Q) and (R). Both (Q) and (R) give yellow precipitate with NaOI. Identify the mixed ether (P) :
- [figure]
- [figure]
- [figure]
- [figure]
Answer
(2) [figure]
Solution
R-O-R' + 2HI RI + R'I + H2O, then RI aq. NaOH ROH
Both alcohols must give iodoform both must contain the CH3CH(OH)- group.
(1) Ethyl 1-phenylpropyl ether ethanol (+) and C6H5CH(OH)CH2CH3 (no CH3CH(OH)-) ✗
(2) Ethyl sec-butyl ether CH3CH2I + CH3CHICH2CH3 ethanol, CH3CH2OH (+) and butan-2-ol, CH3CH(OH)CH2CH3 (+) ✓
(3) Benzyl sec-butyl ether C6H5CH2OH (–) and butan-2-ol (+) ✗
(4) Ethyl tert-pentyl ether ethanol (+) and 2-methylbutan-2-ol, a 3° alcohol with no H on the carbinol carbon (–) ✗
(P) is ethyl sec-butyl ether.
Answer: (2)