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Topic: Curved Arrow Mechanism-Arrow Pushing  (Read 3841 times)

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Offline Jessica09

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Curved Arrow Mechanism-Arrow Pushing
« on: November 25, 2013, 10:08:15 PM »
I need help with these three problem. I attempted to do them, but I am stumped.
They are attached.

Offline AlphaScent

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #1 on: November 26, 2013, 11:39:54 AM »
What type of reaction is each reaction?

What is the reactivity of the compounds?

What is the justification for the third mechanism?
If you're not part of the solution, then you're part of the precipitate

Offline AlphaScent

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #2 on: November 26, 2013, 12:41:33 PM »
If you show some attempt at the first two (forum rules) I would be happy to help you work through the answer.
If you're not part of the solution, then you're part of the precipitate

Offline Jessica09

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #3 on: November 26, 2013, 04:07:21 PM »
I tried my best, but I couldn`t finish the second one.

Is the third one correct?
« Last Edit: November 26, 2013, 04:46:36 PM by Jessica09 »

Offline Jessica09

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #4 on: November 26, 2013, 04:47:15 PM »
If you show some attempt at the first two (forum rules) I would be happy to help you work through the answer.

My attempt is above. Thanks for helping me :)

Offline Babcock_Hall

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #5 on: November 26, 2013, 08:24:55 PM »
Your reaction involving pyridine looks basically OK, but the reaction might be concerted.  Your instructor may not be concerned with that level of detail, however.  YOur reaction involving acetone has a problem in that near the end, you seem to have lost a methyl group.

Offline orgopete

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #6 on: November 26, 2013, 10:46:26 PM »
For 1), curved arrows show electron movement. Magnesium(+) doesn't have electrons to donate, nor does it show a bond having formed to it. Although the correct intermediate has resulted, it does so despite the curved arrows.
Author of a multi-tiered example based workbook for learning organic chemistry mechanisms.

Offline AlphaScent

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #7 on: November 27, 2013, 09:20:27 AM »
Babco and orgopete have laid out the important aspects.  To add to orgopete and your understanding, what electrons will add to the carbonyl in the first reaction?
If you're not part of the solution, then you're part of the precipitate

Offline Jessica09

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #8 on: November 27, 2013, 02:57:51 PM »
Since MgBr do not have electrons to donate I used the bond that connects the cyclohexane and MgBr, but I still don`t know what to do after that.

And I found out where the methyl group was missing.
« Last Edit: November 27, 2013, 04:42:31 PM by Jessica09 »

Offline orgopete

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #9 on: November 28, 2013, 03:19:20 AM »
Since MgBr do not have electrons to donate I used the bond that connects the cyclohexane and MgBr, but I still don`t know what to do after that.

Since the curved arrow signifies a set of directions, you should simply follow them. I understand the ambiguity of using a bond, but since you know a C-C bond Forman the you know the electrons remain attached to the carbon and not the magnesium. Simply draw that product. At this point, nothing more happens. On to the next step and next reagent.
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Offline spirochete

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Re: Curved Arrow Mechanism-Arrow Pushing
« Reply #10 on: November 28, 2013, 11:08:08 PM »
In a grignard reaction the likely initial product will be an alkoxide where the negative oxygen is coodinated to magnesium. Then the alkoxide is protonated during the aqueous work up.

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