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Chem organic question

Hi, please could I have help on statement 2 of this question? Please could someone explain whether sn1 is slower, is it because the c- halogen bond has to break first whereas in sn2 both happen at the same time?
Question: https://ibb.co/hBpxNLK
Thanks!
(edited 4 months ago)

Reply 1

Original post by anonymous56754
Hi, please could I have help on statement 2 of this question? Please could someone explain whether sn1 is slower, is it because the c- halogen bond has to break first whereas in sn2 both happen at the same time?
Question: https://ibb.co/hBpxNLK
Thanks!

SN1 is faster than SN2 in this case, since the presence of a protic solvent (in this case water) helps to stabilise the carbocation intermediate (and there isn’t really anything going on to stabilise a transition state as such so Ea for the formation of a transition state is quite high), so the substrate will react faster than the 1°.

I would be inclined to argue that statement 2 is false because it subtly implies a need for a transition state in the mechanism rather than a carbocation when you have a tertiary substrate (since it discusses a larger dipole rather than ease of formation of a carbocation).

Reply 2

Original post by TypicalNerd
SN1 is faster than SN2 in this case, since the presence of a protic solvent (in this case water) helps to stabilise the carbocation intermediate (and there isn’t really anything going on to stabilise a transition state as such so Ea for the formation of a transition state is quite high), so the substrate will react faster than the 1°.
I would be inclined to argue that statement 2 is false because it subtly implies a need for a transition state in the mechanism rather than a carbocation when you have a tertiary substrate (since it discusses a larger dipole rather than ease of formation of a carbocation).

The markscheme says statement 2 is false?

Reply 3

Original post by anonymous56754
The markscheme says statement 2 is false?

As I explained in my above post - statement 2 implies that the substrate undergoes SN2 rather than SN1, which is incorrect. The substrate does react the most rapidly, but not for the given reason.

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