Question

The question is: What is the product of the reaction of 2-Hexene with CHCl3 in the presence of potassium tert-butoxide?


I chose B:

I thought Potassium tert-but oxide is more likely to act as a base. I thought that it pulls the proton off of CHCl3, because the chlorine groups could hold the stabilize the negative charge, and then CHCl3 adds to the double bond. But this idea is wrong..

Answer 1

In case it can't be seen

Answer 2

I have no Idea but is it the A?

Answer 3

I'm thinking it is B as well but I'm not 100% sure but I know it's not A because that would be the reaction of Cl2 instead of CHCl3

Answer 4

@taramgrant0543664 That's exactly what i thought

Answer 5

but for whatever reason it's wrong

Answer 6

Do you know which one is right?

Answer 7

im pretty sure its D

Answer 8

D was my next thought but I can't picture how that reaction would go

Answer 9

This is what I thought of at first

Answer 10

@aaronq @taramgrant0543664 D is correct

Answer 11

but I can't see how it would go..

Answer 12

its similar to that, CHCl3 gets deprotonated by t-butoxide, then the carbanion attacks the double bond and pushes the electrons to carbon 3, then that carbanion attacks intramolecualry

Answer 13

oooh...

Answer 14

Reacting with CHCl3 and a base makes a cyclo.

Answer 15

@aaronq okay I see it now, the carbanion attacks the other carbon and removes the chlorine and then creates the cyclic structure.

Answer 16

@JoannaBlackwelder to me I always have in my mind that three ring structures are unstable especially if they have large groups attached to them

Answer 17

Yeah, true

Answer 18

especially with those chlorines that's why i didn't consider that one at first