What is the name of the compound CH_3CH_2S(CH_3)_2 and How does the following reaction happen?

CH_3CH_2S(CH_3)_2 + C_2H_5ONa ->CH_3 CH_2OC_2H_5 + H_2C=CH_2
Where, substitution = 88% and elimination = 12% . The reaction takes place in presence of ethanol.

EDIT: Added missing product: "S"("CH"_3)_2
- Truong-Son

1 Answer
Feb 22, 2018

Here's what I get.

Explanation:

The nucleophile/base is ethoxide ion, "CH"_3"CH"_2"O"^"-".

The substrate is the ethyldimethylsulfonium ion, "CH"_3"CH"_2stackrelcolor(blue)("+")("S")("CH"_3)_2

The positive charge on the "S" atom makes the dimethylsulfonium ion an excellent leaving group.

The S"_text(N)2 displacement reaction

The ethoxide acts as a nucleophile and attacks the α-carbon.

SN2SN2

The "E2" reaction

The ethoxide acts as a base and attacks the β hydrogen

E2E2