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Old 09-05-2014, 03:34 PM  
'Hamas' Jenkins 'Hamas' Jenkins is offline
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Organic Chemistry Question
This one has me totally vexed. Any help you could offer on where to put the arrows would be greatly appreciated.




It looks like it's already done. I'm not sure if I should approach it as conjugated pi bonds or not.
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Old 09-05-2014, 07:05 PM   #31
DrunkBassGuitar DrunkBassGuitar is offline
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Quote:
Originally Posted by Cunning Linguist View Post
You haven't really provided any solution, other than describing what you see. OP can do that, but he needs a solution other than "it's already done, and this is happening" offered by others.
it's not done, I was trying to describe why it can't be done (which is why the N had the negative charge and C with the positive in my post), the question is basically asking to push electrons.

I don't think I was very clear with what I wrote, and what you wrote is totally correct. it's asking for a mechanism, what is drawn in the question isn't totally right, which is what I was attempting (obviously very poorly) to communicate. you can't just move the double bond, since the N's electron pair have to go somewhere. again, I should have written that post better. better as in finishing the thought. I'm terrible at teaching over the internet (and in general)
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Old 09-05-2014, 07:13 PM   #32
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Quote:
Originally Posted by 'Hamas' Jenkins View Post
Ok, so moving the lone pair on the last benzene ring on the carbon with the negative formal charge to form a double bond in the upper left hand corner is correct, but my attempts for the other three were not.
what were your attempts for the other 3?
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Old 09-05-2014, 07:21 PM   #33
Don Corlemahomes Don Corlemahomes is offline
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Quote:
Originally Posted by DrunkBassGuitar View Post
it's not done, I was trying to describe why it can't be done (which is why the N had the negative charge and C with the positive in my post), the question is basically asking to push electrons.

I don't think I was very clear with what I wrote, and what you wrote is totally correct. it's asking for a mechanism, what is drawn in the question isn't totally right, which is what I was attempting (obviously very poorly) to communicate. you can't just move the double bond, since the N's electron pair have to go somewhere. again, I should have written that post better. better as in finishing the thought. I'm terrible at teaching over the internet (and in general)
No worries man. You're good.
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Old 09-05-2014, 07:22 PM   #34
'Hamas' Jenkins 'Hamas' Jenkins is offline
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I think I may have the first and last.

If you move the lone pair on the Amine group to form a double bond and then break the pi bond in the upper right hand corner of the benzene ring, giving that lone pair to the carbon in the upper right hand corner, that should work for #1

#4 works when I break the pi bond connecting the amine group to the nitrogen, giving it a lone pair.
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Old 09-05-2014, 07:22 PM   #35
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Originally Posted by Cunning Linguist View Post
No worries man. You're good.
well I looked at my post again after you replied and I'm like "yeah, what I wrote was hilariously wrong"

but the picture should be the right mechanism
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Old 09-05-2014, 07:25 PM   #36
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Got it.
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Old 09-05-2014, 07:25 PM   #37
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Quote:
Originally Posted by 'Hamas' Jenkins View Post
I think I may have the first and last.

If you move the lone pair on the Amine group to form a double bond and then break the pi bond in the upper right hand corner of the benzene ring, giving that lone pair to the carbon in the upper right hand corner, that should work for #1

#4 works when I break the pi bond connecting the amine group to the nitrogen, giving it a lone pair.
so for 2 and 3 you're just shifting that lone pair. you can use it to form a double bond, and since you can't have 2 adjacent double bonds on that structure you can break the other bond
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Old 09-05-2014, 07:27 PM
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Old 09-05-2014, 07:28 PM   #38
Don Corlemahomes Don Corlemahomes is offline
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Ah so you can use the lone pair.
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Old 09-05-2014, 07:29 PM   #39
'Hamas' Jenkins 'Hamas' Jenkins is offline
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I started out by erasing the arrows, which were put there by a devious one who sucks the penis who should have his pisshole reamed out with a toilet brush. From there, it was pretty straightforward.

I have no ****ing idea why they'd put the goddamn arrows there. All it does is **** up the understanding of the problem.

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Old 09-05-2014, 07:32 PM   #40
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Old 09-05-2014, 07:49 PM   #41
Don Corlemahomes Don Corlemahomes is offline
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Originally Posted by 'Hamas' Jenkins View Post
I started out by erasing the arrows, which were put there by a devious one who sucks the penis who should have his pisshole reamed out with a toilet brush. From there, it was pretty straightforward.

I have no ****ing idea why they'd put the goddamn arrows there. All it does is **** up the understanding of the problem.
Glad you got it! Good work. May I ask why you are taking Organic?
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Old 09-05-2014, 07:52 PM   #42
'Hamas' Jenkins 'Hamas' Jenkins is offline
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Glad you got it! Good work. May I ask why you are taking Organic?
Career change. One of 12 classes I need to take to knock down pre-reqs for pharmacy school. Eventually, I want to be a nuclear pharmacist.
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Old 09-05-2014, 07:56 PM   #43
Don Corlemahomes Don Corlemahomes is offline
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Career change. One of 12 classes I need to take to knock down pre-reqs for pharmacy school. Eventually, I want to be a nuclear pharmacist.
Badass. Good luck.
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Old 09-05-2014, 08:59 PM   #44
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Old 09-05-2014, 09:10 PM   #45
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