orgo question

[hope_to_match]

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wouldn't Cl end up on the tertiary carbon due to a hydride shift? Thanks

 

[Jordwin]

Since it's in ether it is in an aprotic solvent which will only be sn2 or e2, so no carbocation or rearrangements. And it is sn2 because hcl is a strong nucleophile. Hope this helps

 

[hope_to_match]

Since it's in ether it is in an aprotic solvent which will only be sn2 or e2, so no carbocation or rearrangements. And it is sn2 because hcl is a strong nucleophile. Hope this helps

thanks it does..

i was confusing this with a reaction with just HCl with no ether. In that case there would be rearrangement right? It's rxn#1 on the alkene list from Chad..am I correct?

 

[Jordwin]

Yep you are correct!

 

[hope_to_match]

Yep you are correct!

ok thanks. i have to make sure not to confuse the two 😎 in the future

 

[Jordwin]

Also, on that reaction, the Cl is less selective than br so you will get a mixture of products opposed to the Br that will have the most substituted carbon being the location the halogen (Br) is added.

 

[hope_to_match]

Also, on that reaction, the Cl is less selective than br so you will get a mixture of products opposed to the Br that will have the most substituted carbon being the location the halogen (Br) is added.

doesnt that only apply to free radical halogenation?

 

[Jordwin]

True, I guess I just assumed they were the same since the carbocation and radicals get stabilized with the same effects. I bet you are right, the radicals must be a special case. Good call.

 

[hope_to_match]

True, I guess I just assumed they were the same since the carbocation and radicals get stabilized with the same effects. I bet you are right, the radicals must be a special case. Good call.

well for free radical halogenation the reactants are different (Br2/CL2 with light or heat or ROOR)

no problem. i think discussing things makes this stuff stick if you know what i mean

 

[Jordwin]

Yes, very true. It's the best way to learn!