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Topic: Amine Questions  (Read 5902 times)

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Offline Lego_12

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Amine Questions
« on: June 13, 2013, 01:07:16 AM »
[ATTACH=CONFIG]226190[/ATTACH]

My problem is I cannot see what is happening.

I believe it is a nucleophillic addition-elimination reaction/mechanism but I am unable to draw it out as I cannot see what to do.


[ATTACH=CONFIG]226192[/ATTACH]nnn

Here I want to know if it is ok to explain what is going on in words, if not I do not know the correct equation in stages to show how it progresses.


also how would you draw out these substances in display formula

(b)(i) Primary: CH3CH(NH2)CH3, Secondary: NH(CH3CH2)(CH3), Tertiary: N(CH3)3

Offline discodermolide

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Re: Amine Questions
« Reply #1 on: June 13, 2013, 01:10:18 AM »
[ATTACH=CONFIG]226190[/ATTACH]

My problem is I cannot see what is happening.


(b)(i) Primary: CH3CH(NH2)CH3, Secondary: NH(CH3CH2)(CH3), Tertiary: N(CH3)3


neither can we, your attachments did not show up. Use the additional options button below the posting frame
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Offline discodermolide

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Re: Amine Questions
« Reply #3 on: June 13, 2013, 01:17:07 AM »
For question 2 you need to add an extra carbon and a nitrogen to BrCC
What nucleophile has these components?
What nitrogen nucleophiles do you know of?

For question 1 this is an acylation reaction, draw out the starting materials and have a go at drawing the product
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Offline Lego_12

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Re: Amine Questions
« Reply #4 on: June 13, 2013, 01:30:01 AM »
For question 2 you need to add an extra carbon and a nitrogen to
What nucleophile has these components?
What nitrogen nucleophiles do you know of?

I cannot see what you are trying to tell me

For question 1 this is an acylation reaction, draw out the starting materials and have a go at drawing the product

I know this from somehwere but I need some visual aid to trigger.

Offline discodermolide

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Re: Amine Questions
« Reply #5 on: June 13, 2013, 01:42:46 AM »
For question 2 you need to add an extra carbon and a nitrogen to
What nucleophile has these components?
What nitrogen nucleophiles do you know of?

I cannot see what you are trying to tell me

For question 1 this is an acylation reaction, draw out the starting materials and have a go at drawing the product

I know this from somehwere but I need some visual aid to trigger.


You need to add a carbon and a nitrogen to get your product.
This can be done by nucleophillic substitution of the bromine atom by a CN  nucleophile, do you know one?


Think about the structure of amides, can you draw one?

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Offline Lego_12

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Re: Amine Questions
« Reply #6 on: June 13, 2013, 02:07:29 AM »

Offline Lego_12

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Re: Amine Questions
« Reply #7 on: June 13, 2013, 02:08:32 AM »
I honestly cannot do the first one could you help me by doing the 1st stage.

Offline discodermolide

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Re: Amine Questions
« Reply #8 on: June 13, 2013, 02:22:54 AM »
What you have drawn looks ok, but it is a bit upside-down!
The other one starts with the following reaction.
Now you figure out how to go from there to your product.

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Offline Lego_12

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Re: Amine Questions
« Reply #9 on: June 13, 2013, 02:38:42 AM »
so are you sure I got the other one I just scanned up correct, can you check please?

Offline discodermolide

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Re: Amine Questions
« Reply #10 on: June 13, 2013, 02:41:24 AM »
The acetyl chloride acylated the amine to give the amide.
CC(NCCC)=O
« Last Edit: June 13, 2013, 03:06:31 AM by discodermolide »
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Offline Lego_12

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Re: Amine Questions
« Reply #11 on: June 13, 2013, 03:01:16 AM »


M-propylethanamide


Correct?

Offline discodermolide

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Re: Amine Questions
« Reply #12 on: June 13, 2013, 03:06:06 AM »
N-propylacetamide
Sorry I added an extra carbon which I will correct.
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Offline Lego_12

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Re: Amine Questions
« Reply #13 on: June 13, 2013, 03:10:19 AM »
so it's N-propylacetamide

but my working out is good to support the fact that it was nucleophillic addition-elimination reaction

Offline discodermolide

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Re: Amine Questions
« Reply #14 on: June 13, 2013, 03:14:33 AM »
Yes, the mechanism you showed is fine.
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