[axaplast]

Will propanenitrile, CH3CH2CN, yield propylamine, CH3CH2CH2NH2 upon hydrolysis? If so, can you help me with the equation?

[AWK]

No, you need reduction instead.

[axaplast]

Can you provide me with the general reaction for forming amines by hydrolysis?

[agrobert]

You can hydrolyze a nitrile to an amide under certain acid-hydrolysis but you need reduction (as stated above) to yield an amine.  Propyl amine can be synthesized by reductive amination of propyl aldehyde.

[axaplast]

Thanks for the posts thus far. My organic chemistry instructor has told us that one of the following compounds gives propylamine, CH3CH2CH2NH2, upon hydrolysis:

CH3CNHCH2CH2CH3
     ║   
     O

(CH3CH2CH2)2NH

CH3CH2CH
     ║
     NH

CH3CH2C≡N

This is beyond the scope of material in our textbook and I have rearched on the internet and found the following information about amine reactivity that states primary amines can be formed through hydrolysis using NaOH solutions, with the general reaction being:

Initial product: R3C-NHCONH2
Final product: R3C-NH2

I still do not understand how to apply this general reaction to the question at hand. Can anyone provide some help?

 


 

[azmanam]

One of your multiple choices is exactly analogous to the initial 'product' (i think you mean starting material).  It's drawn a bit differently, though.

See ester hydrolysis (or saponification) in your book for mechanism.

see here for hints
http://www.cem.msu.edu/~reusch/VirtTxtJml/crbacid2.htm#acderv