Amide Hydrolysis - Video Tutorials & Practice Problems
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1
concept
Acidic Hydrolysis Concept 1
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Hey, everyone. So we're gonna take a look at acidic hydrolysis of amides. Now, we're going to say that under this reaction, an amide is hydrolyzed into a carbolic acid and ammonium ion in an acidic medium. Now, if we take a look at this general reaction, we have our amide here and with it, our amide bond that connects our nitrogen to our carbon group. Under this reaction, we use basically aqueous acid, meaning that we have hydrochloric acid dissolved in water and we accompany it with heat. Basically. What happens is that in this reaction, the carbon carbon, it is going to gain an oh doing this, transforms it into a carbolic acid. And at the same time, we're gonna have the nitrogen itself gains two hydrogen atoms and thereby becomes an ammonium ion. Remember when nitrogen makes four bonds, it becomes positively charged, it transitions from being a neutral amine to an ammonium ion. So just remember under acidic hydrolysis, we make a carbolic acid and ammonium ion
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example
Acidic Hydrolysis Example 1
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Determine the products when 33 dimethyl hexen amide is treated with an aqueous hydrochloric acid solution. So remember in this reaction, we're going to cut this amide bo and what's going to occur is that the carbon carbon gains an oh group. So we create a carbolic acid. At the same time, the nitrogen itself will gain two hydrogen atoms. So nitrogen already contains uh two hydrogens and it's gonna gain another two. So at the end, we'll have four hydrogens on the nitrogen. And are we making four bonds? So it'll be positively charged. So here we make an ammonium ion as the second product. So this would be our answer for this particular example question. We created a carbolic acid and the ammonium ion.
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Problem
Problem
Name the carboxylic acid formed when the following amide undergoes an acidic hydrolysis reaction.
A
2-bromopentanoic acid
B
3-bromohexanoic acid
C
3-bromopentanoic acid
D
3-bromohexanoate
4
concept
Basic Hydrolysis Concept 2
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In this video, we're gonna take a look at basic hydrolysis of amides. Now, under this reaction, we're gonna say that the hydroxide ion which is oh minus dissolved in water reacts with an amide. Now, the reaction cleaves or cuts the amide bond to create a carboxylate an ion and in amine. Now, if we take a look here at this general reaction, we're gonna cut this amide bond, we're using it by using uh aquis hydroxide. So that just means it's dissolved in water and accompanied by some heat. So basically what happens here is that the carbon carbon will gain a O negative because a carboxylate, an ion is just the conjugate base form of a carbolic acid. So instead of having an oh group, it has an O minus group and the nitrogen here would only gain one hydrogen atom. So here we create a neutral amine. So under basic conditions, we're not making a carbolic acid, we're making its conjugate base, which is our carboxylate an ion. And for the amine, it's going to be a neutral amine that's being formed
5
example
Basic Hydrolysis Example 2
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52s
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Determine the products when N ethyl and methyl butane amide is treated with an aqueous hydroxide ion solution. Now, before we do this question, remember when it comes to our N substituents, you have to have your n capitalized and italicized, right? So that's the name of this particular remind. Now, under this reaction under basic hydrolysis, we're going to cut the amide bond. When we do that, we're gonna make a carboxylate an ion. So the carbonel group gets an O negative attached to it and then the amide, well, the nitrogen part of the amide that nitrogen, all it's gonna do is gain one hydrogen and stay as a neutral amine, right? So in this particular question, we make a carboxylate anion product as well as a neutral amine.
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Problem
Problem
Determine the carboxylate anion formed in the following reaction between the given amide and aqueous base.
A
B
C
D
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Problem
Problem
Determine the nitrogen product formed when the following amide undergoes acidic hydrolysis.
A
B
C
D
8
Problem
Problem
What was the starting material that created the following products?
A
B
C
D
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