Question

How would one go about synthesizing benzyl methyl ether via Williamson-Ether Synthesis from these chemicals available? The 5 chemicals (with red caps) in the top row from left to right are: 2-Chloro-norbornane, Benzyl chloride, 2-Chloro-2-methyl propane, 4-Chloro-1-butanol, and Chlorobutane.

Second question: What is the mechanism for said reaction? (formula)
Reactions EXIT +-C1 HOMCI 9:39 Esterification Alcohol Halogenation Alkyl Halide Solvolysis Alkene Hydration Hydroboration Alkene Bromination Alkene Dihydroxylation Epoxidation Diels Alder Aldol Grignard Addition Benzene Nitration Friedel-Crafts Add Chloride Carbonyl Reduction Claisen Condensation Alcohol Oxidation EtOH Et,o ci i ICE Spectra s MCPBA AICI, NaBHPCC CH,SO.HCI BH, Brz KOHLDA HNO. SOC. Nao Me H.Cr.0, Н,0 1. NaOH На Е. Co-O"

Answer 1

synthesizing benzyl methyl ether via Williamson-Ether Synthesis :

Williamson Ether Synthesis, proceeds by an SN2 reaction of an alkoxide nucleophile with an alkyl halide.

we choose Alkyl Halide : Benzyl chloride

As source of alkoxide nucleophile ( Mexthoxide ) :we choose : NaOMe (Sodium methoxide)

Benzyl chloride + NaOMe     (Since MeOH is not available we shall Use water as Solvent)

Mechanism :
Na+ OMe-   ---->Ph- CH2-Cl       =====>   Ph-CH2-OMe + NaCl               ( SN2 reaction )