Is Williamson Ether Synthesis an SN1 or SN2 reaction?

1 Answer
Jun 21, 2016

#S_N2#

Explanation:

First, it is necessary to understand the difference between an #S_N1# and an #S_N2# mechanism.

An SN1 mechanism is a two-step mechanism and racemization occurs:

  1. Departures of the leaving group#->#formation of carbocation
  2. Nucleophilic attack (usually a weak nucleophile) on carbocation#->#racemic product
    enter image source here
    An SN2 mechanism is a concerted (one-step) mechanism:

  3. Nucleophile attacks (strong nucleophile) from backside of leaving group #->#product has inverted stereochemistry
    enter image source here

A Williamson Ether synthesis is carried out using an alcohol and an alkyl halide. First, the alcohol is deprotonated using a strong base to create an alkoxide anion as shown in the reaction below:

#ROH + B^-##rightleftharpoonsRO^-##+BH#

When the alkyl halide is added to the reaction, the alkoxide anion (#RO^(-)#) will act as a nucleophile and displace the halide connected to the electrophilic carbon in a concerted (one-step) reaction.

For example:
enter image source here

Note: The ether product will have opposite stereochemistry to the original alkyl halide at the electrophilic carbon