18. The Williamson Ether Synthesis is fundamentally an SN2 reaction between an alkoxide and an alkyl halide. A researcher attempted to synthesize cysleheslethyl ether using the Williamson Ether Synthesis as shown below +Na* -OCH2CH3 +Nal OCH2CH3 Analysis of the organic product by IR spectroscopy revealed a weak peak at 1645 cm1 and a medium-sized peak at 3085 cm1. There was no evidence of a C-O bond. The experiment had failed. Suggest an explanatiorn Reaction of a strong base with a secondary alky1 halide produces an alkene by an E2 mechanism. The secondary alkyl halide was too sterically hindered, so no reaction occurred. a. c. The ethoxide anion is not a strong enough nucleophile to displace the iodine leaving group. d. The iodine is not a good enough leaving group for this type of reaction. Solution answer: a as sodium ethoxide(NaOC2H5) is strong base it removes proton from alkylhalide carbon ,followed by loss of halide ion. so that, elemination product alkene will be formed. .

1. 18. The Williamson Ether Synthesis is fundamentally an SN2 reaction between an alkoxide and
an alkyl halide. A researcher attempted to synthesize cysleheslethyl ether using the Williamson
Ether Synthesis as shown below +Na* -OCH2CH3 +Nal OCH2CH3 Analysis of the organic
product by IR spectroscopy revealed a weak peak at 1645 cm1 and a medium-sized peak at 3085
cm1. There was no evidence of a C-O bond. The experiment had failed. Suggest an explanatiorn
Reaction of a strong base with a secondary alky1 halide produces an alkene by an E2
mechanism. The secondary alkyl halide was too sterically hindered, so no reaction occurred. a. c.
The ethoxide anion is not a strong enough nucleophile to displace the iodine leaving group. d.
The iodine is not a good enough leaving group for this type of reaction.
Solution
answer: a
as sodium ethoxide(NaOC2H5) is strong base it removes proton from alkylhalide carbon
,followed by loss of halide ion. so that, elemination product alkene will be formed.