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Topic: Diazonium salt reaction  (Read 2870 times)

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Offline ricecake

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Diazonium salt reaction
« on: March 20, 2015, 10:04:54 PM »
Actylene + H2O + Hg2+/H+  :rarrow: A + NH3 + H2/Ni,t°  :rarrow: B  + NaNO2 + HCl, 0-5°C :rarrow: C + propanoic acid + H2SO4/t°  :rarrow: D

I was not sure about he diazonium part...So far I got
A is acetylaldehyde (ethanal)
B is ethylamine
C is N≡N+CH2CH3
D is CH3CH2CON=NCH2CH3
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Offline Dan

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Re: Diazonium salt reaction
« Reply #1 on: March 21, 2015, 04:42:32 AM »
Quote from: ricecake on March 20, 2015, 10:04:54 PM
I was not sure about he diazonium part

Alkyl amines give diazo compounds (not diazonium salts).

See: http://en.wikipedia.org/wiki/Diazo

Read about their chemistry and re-think your last step.
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Offline ricecake

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Re: Diazonium salt reaction
« Reply #2 on: March 21, 2015, 08:45:24 AM »
Thank you so much for your help. I hope I'm closer to the correct answer this time.

C would be N=NCH2C3
D would be CCC(O)=NNCC

« Last Edit: March 21, 2015, 09:26:17 AM by ricecake »
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Offline Dan

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Re: Diazonium salt reaction
« Reply #3 on: March 21, 2015, 09:36:27 AM »
Quote from: ricecake on March 21, 2015, 08:45:24 AM
C would be N=NCH2C3

Not quite - I guess you mean N=NCHCH3 - check the valency at the C bonded to N; compare to the structure of diazomethane.

Quote
D would be CCC(O)=NNCC

No, I don't think so. How does diazomethane react with carboxylic acids?
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Offline ricecake

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Re: Diazonium salt reaction
« Reply #4 on: March 21, 2015, 11:10:49 AM »
Thank you for being really patient.
Am I in the right direction?

C is [n-]=[n+]=CC
D is CCC(=o)oCC
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Offline Dan

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Re: Diazonium salt reaction
« Reply #5 on: March 21, 2015, 04:34:37 PM »
I think that's right - well done
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