Question

Which of the following on heating gives an ether as major products?
P: $C_6H_5CH_2Br + CH_3ONa$
Q: $C_6H_5ONa + CH_3Br$
R: $(CH_3)_3C-Cl+CH_3ONa$
S: $C_6H_5CH = CHCl + CH_3ONa$

• A. Both R and S
• B. Both P and R
• C. Both Q and S
• D. Both P and Q

Answer 1

Answer: (D)

Primary alkyl halides/ benzyl halides react with alkoxide/phenoxide to give ethers via $S _{N} 2$ mechanism. This reaction is known as Williamson's ether synthesis. Aryl halides are the least reactive as the $C-X$ bond has a partial double bond characteristic and hence, does not cleave easily. $3^{\circ}$ halides do not give ethers as they undergo elimination in the presence of a strong base like alkoxides.