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organic II


Thread replies: 6
Thread images: 1

I just got out of an exam for my organic II exam, and there were two questions i can't really seem to find the answer to online anywhere. these were my answers, but I'm not sure if they're correct. can anyone help?
>>
>>7950465
number 2 is correct (not sure if you were also supposed to specify some weak acid to catalyze it).

there's something wrong with number 1: cyclohexane is not very nucleophilic, probably you are not recalling the presence of some functional group.
Furthermore, under Lewis acidic conditions the epoxide will be attacked at the more hindered position.
>>
>>7950518
seconded

#1 wouldn't react under those conditions.
>>
>>7950518
>>7950523
If it was benzene, would that change it? I'm pretty sure there weren't any substituents on the ring. I was pretty confused. His hint was "Oxygen loves Aluminum!" which I'm not sure what was intended by that. I've never really seen AlCl3 used outside Diehls Alder, anyway
>>
>>7950529
>If it was benzene
https://en.wikipedia.org/wiki/Electrophilic_aromatic_substitution
https://en.wikipedia.org/wiki/Friedel%E2%80%93Crafts_reaction
The second link does invoke lewis acid/epoxide as a suitable electrophile, although no citation is given.
>>
>>7950529
If it was benzene, I think what you have might be it, but there is no H+ as written. Basically, the epoxide would complex with the AlCL3, making the right carbon bonded to the oxygen elctrophilic enough to be attacked by a pi bond in benzene.
Thread replies: 6
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