mani93786
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Someone explain how the answer is D?
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mani93786
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Anyone?
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mani93786
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Please someone help
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laurawatt
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Moved to the chemistry forum
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mani93786
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Still no answer
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Kian Stevens
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It's just a big complicated nucleophilic substitution reaction...

Ammonia will attack the carbon of one of the C-Br bonds with its lone pair, and so it'll replace Br with NH2
However, this NH2 group can do exactly the same thing with the other C-Br bond

If you follow it through -- you don't even need to complete the mechanism -- you'll see that the answer has to be D in order to produce coniine this way
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mani93786
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(Original post by Kian Stevens)
It's just a big complicated nucleophilic substitution reaction...

Ammonia will attack the carbon of one of the C-Br bonds with its lone pair, and so it'll replace Br with NH2
However, this NH2 group can do exactly the same thing with the other C-Br bond

If you follow it through -- you don't even need to complete the mechanism -- you'll see that the answer has to be D in order to produce coniine this way
But how do you get a cyclic compound (coniine) from an acyclic compound (1,5-dibromooctane). I’m really confused about this and still don’t get how the answer is D. Also as far as I know, a nucleophilic substitution with ammonia will produce an amine as it will go through the NH3 intermediate then lose the hydrogen to become NH2. But this compound (coniine) only contains one hydrogen so how come?

If you could please explain this that would be appreciated. Thanks
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Kian Stevens
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(Original post by mani93786)
But how do you get a cyclic compound (coniine) from an acyclic compound (1,5-dibromooctane). I’m really confused about this and still don’t get how the answer is D. Also as far as I know, a nucleophilic substitution with ammonia will produce an amine as it will go through the NH3 intermediate then lose the hydrogen to become NH2. But this compound (coniine) only contains one hydrogen so how come?

If you could please explain this that would be appreciated. Thanks
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Here's the mechanism for the reaction
As you can see, yes an amine is formed... But the NH2 group in the amine can also react with the other C-Br bond as well
All this is shown in the image
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annoymous_
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I read cocaine lol sorry I’m no help
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mani93786
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(Original post by Kian Stevens)
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Here's the mechanism for the reaction
As you can see, yes an amine is formed... But the NH2 group can also react as well
All this is shown in the image
Thank you so much!!
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Kian Stevens
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(Original post by mani93786)
Thank you so much!!
I'm glad you've finally got your problem sorted...!
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mani93786
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So it’s a secondary amine? What would be it’s IUPAC name?
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Kian Stevens
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(Original post by mani93786)
So it’s a secondary amine? What would be it’s IUPAC name?
Yes it's a secondary amine

Its IUPAC name is 2-propylpiperidine
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