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
icon
Related questions
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

trending now

Trending now

This is a popular solution!

steps

Step by step

Solved in 2 steps

Blurred answer
Knowledge Booster
Ammonium Salts
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.
Similar questions
  • SEE MORE QUESTIONS
Recommended textbooks for you
Organic Chemistry: A Guided Inquiry
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:
9780618974122
Author:
Andrei Straumanis
Publisher:
Cengage Learning