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Chemistry Forums for Students => Undergraduate General Chemistry Forum => Topic started by: graditz on April 19, 2016, 10:50:45 PM

Title: Amide hydrogenation reaction?
Post by: graditz on April 19, 2016, 10:50:45 PM

I'm having a little trouble understanding how an amide reacts with Hydrogen in a specific case: under high pressure, at high temperature, and in the presence of a platinum catalyst. My understanding is that it will be reduced to an amine. I have attached an image illustrating the hydrolysis of this unknown amide (X), producing an amine and an acid. Nonetheless, the addition of hydrogen should replace the C=O with two C-H bonds, correct? If this is the case, what will happen if (Y) is hydrolyzed? Assuming it is an amine, would the reaction be acid-base? Still, would that just mean that the N-H bond becomes NH₂? Thank you for the assistance!

Title: Re: Amide hydrogenation reaction?
Post by: discodermolide on April 20, 2016, 12:53:36 AM

I think the clue here is 3H₂. What else in your molecule can be reduced by hydrogen?

Title: Re: Amide hydrogenation reaction?
Post by: graditz on April 20, 2016, 03:01:05 PM

Ah, so the phenyl group would be hydrogenated to cyclohexane and the carbonyl group would remain? Then, when (Y) is hydrolyzed, the water molecule will replace the carbonyl group to form (Z), correct?

Title: Re: Amide hydrogenation reaction?
Post by: discodermolide on April 21, 2016, 01:22:00 AM

Structure for Y looks OK. Now how do amides hydrolyse?
What products do you obtain?

Title: Re: Amide hydrogenation reaction?
Post by: graditz on April 21, 2016, 01:40:31 AM

Quote from: discodermolide on April 21, 2016, 01:22:00 AM

Structure for Y looks OK. Now how do amides hydrolyse?
What products do you obtain?

Thanks! I figured it out.