Question

E2 or SN2?

Answer 1

@Kainui

Answer 2

Hi :3

Answer 3

Hey. :) Any ideas?

Answer 4

Specifically arguments for/against each case :P

Answer 5

With secondary substrates, if the nuceophile is strong, it could favor E2 and Sn2. BUT if there's a strong base, then it will favor E2. Is it E2?

Answer 6

However, there's also factors that can make this an E2 such as the presence of Heat and Bulky groups as well as a strong base....

Answer 7

But at the same time, it can be Sn2

Answer 8

Because Ots is a good LG

Answer 9

i'm confused :x

Answer 10

True, you will definitely have both SN2 and E2, plus tosylate is a great leaving group.

The ring itself is not very helpful for doing nucleophilic reactions since it's hard to get a nucleophile to penetrate the backside. Additionally, secondary carbons generally go mostly by E2 so that last thing I mentioned is probably just enough to make that certain.

Some other reasons other than it being simply hindered a little to do a nucleophilic reaction is in a simple sorta statistical way it looks like there are 2 different ways you can do an elimination reaction here while there's only one way to do a nucleophilic reaction:

A strong base tends to favor SN2 with primary carbons and E2 with secondary and tertiary carbons while weak bases like halogens however tend to favor SN2 for primary and secondary carbons.