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Topic: Synthesis problem 2-Aminopropanoic + CH3CHO  (Read 2920 times)

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Offline ricecake

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Synthesis problem 2-Aminopropanoic + CH3CHO
« on: December 06, 2014, 05:47:53 PM »
Please help me with this problem.
2-Aminopropanoic + CH3CHO  :rarrow: A + H2/Ni/t°  :rarrow: B + t°/-CO2 :rarrow: C + CH3H7Br (1:1)  :rarrow: D

I was really confused on A  ??? I was thinking A would be an imine.
 
Would this be the correct answer for A: CH3CH=NCHCH3COOH
Thank you so much!

Offline Altered State

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Re: Synthesis problem 2-Aminopropanoic + CH3CHO
« Reply #1 on: December 06, 2014, 08:12:52 PM »
You are right. Amine + aldehyde yields an imine:


Offline ricecake

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Re: Synthesis problem 2-Aminopropanoic + CH3CHO
« Reply #2 on: December 07, 2014, 02:19:04 PM »
Thank you so much! I was confused because I was not sure if carboxylic OOH or primary amine has higher nucleophilicity. 

H2/Ni/t° is a hydrogenation reaction in general so
B would be CH3CH2NHCHCH3COOH

I was a bit iffy on C   CH3CH2NHCH2CH3

D  would be CH3CH2CH3H7

Offline ricecake

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Re: Synthesis problem 2-Aminopropanoic + CH3CHO
« Reply #3 on: December 08, 2014, 06:04:02 PM »
CC(N)C(=O)O + CC(=O) (aldehyde)  :rarrow: CC(C(=O)O)N=CC + H2,Ni,t°  :rarrow: CC(C(=O)O)NCC -CO2  :rarrow: CCNCC +CCCBr (1:1)  :rarrow: CCN(CCCC)CC

Offline AromaticAcrobatic

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Re: Synthesis problem 2-Aminopropanoic + CH3CHO
« Reply #4 on: December 08, 2014, 10:44:35 PM »
Ricecake,
be careful with that final product.
Where did 8 Carbons come from?

 :spinpaired:

Offline ricecake

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Re: Synthesis problem 2-Aminopropanoic + CH3CHO
« Reply #5 on: December 10, 2014, 10:00:30 PM »
CC(N)C(=O)O + CC(=O) (aldehyde)  :rarrow: CC(C(=O)O)N=CC + H2,Ni,t°  :rarrow: CC(C(=O)O)NCC -CO2  :rarrow: CCNCC +CCCBr (1:1)  :rarrow: CCN(CCC)CC

My bad thank you for the correction and comments :D

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