Question

Show how to synthesize allyl phenyl ether and 2-butenyl phenyl ether from phenol and appropriate alkenyl halides.

Short answer

Answer: The key step in synthesizing allyl phenyl ether and 2-butenyl phenyl ether is the Williamson ether synthesis, which involves the reaction of a phenoxide ion with suitable alkenyl halides.

Step-by-step solution

Formation of phenoxide ion from phenol

First, we need to convert phenol into a phenoxide ion. This can be done by treating phenol with a strong base, such as sodium hydroxide (NaOH), which will deprotonate the phenol. Phenol + NaOH -> Phenoxide ion (O-Ph) + H2O

Synthesis of allyl phenyl ether

Next, we need to react the phenoxide ion with an allyl halide (such as allyl bromide, BrCH2CH=CH2) in Williamson ether synthesis to form allyl phenyl ether. Phenoxide ion (O-Ph) + Allyl bromide (BrCH2CH=CH2) -> Allyl phenyl ether (O-Ph-CH2CH=CH2) + Br-

Synthesis of 2-butenyl phenyl ether

Similarly, to synthesize 2-butenyl phenyl ether, we need to react the phenoxide ion with an appropriate alkenyl halide, such as 1-bromo-2-butene (BrCH2=CHCH2CH3). Phenoxide ion (O-Ph) + 1-bromo-2-butene (BrCH2=CHCH2CH3) -> 2-butenyl phenyl ether (O-Ph-CH2=CHCH2CH3) + Br- In summary, Williamson ether synthesis is used to form both allyl phenyl ether and 2-butenyl phenyl ether from phenol and appropriate alkenyl halides.