Why doesn't iodoethane react via Sn2 with NaI in acetone? It is a good leaving group and it is on a primary carbon. I know it is able to react Sn1 quickly.
Why doesn't iodoethane react via Sn2 with NaI in acetone? It is a good leaving group and it is on a primary carbon. I know it is able to react Sn1 quickly.
Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter14: Elimination
Section: Chapter Questions
Problem 8CTQ
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Question
Why doesn't iodoethane react via Sn2 with NaI in acetone? It is a good leaving group and it is on a primary carbon. I know it is able to react Sn1 quickly.
Expert Solution
Step 1 Condition When SN2 favor over SN1
1 .Nature Of Solvent
Solvent | SN1 | SN2 |
Polar Aprotic Solvent (Acetone) | SN2 will favor | |
Polar Protic Solvent (Methanol) | SN1 will favor (Stabilization of carbocation) |
A polar protic solvent can stabilize the carbocation, so favoured SN1
while a polar aprotic solvent favor SN2
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