Questions tagged [amides]

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1answer
78 views

On the stabler tautomer in amide-imidic acid tautomerism

In the section on acid-catalysed hydrolysis of nitriles, this webpage has the following line of reasoning; ...the more stable amide tautomer predominates the (following) equilibrium. (credit) How ...
-2
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0answers
35 views

Why does citrulline have two pka values?

Can someone explain to me why citrulline has two pka values? It has a carboxy group that could donate a proton, but where would the second proton come from? Should the amide group not be more basic ...
0
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0answers
60 views

How would sodium amide react with a non-terminal alkyne? [duplicate]

The reaction of a terminal alkyne with $\ce{NaNH2}$ leads to the loss of hydrogen ion from the terminal carbon. But what will happen if the alkyne is a non-terminal one? How would $\ce{NH2-}$ attack ...
8
votes
1answer
147 views

Can I synthesize an Amide simply by heating an amine and a carboxylic acid (with a vacuum pump)?

I am interested in creating an amide of stearic acid. I thought that simply mixing both of them in some solvent, heating the solution, and using a vacuum pump to distill the liberated water (to drive ...
3
votes
1answer
326 views

Why do amides require much harsher conditions for hydrolysis than esters?

Amides require much harsher conditions to hydrolyse than its ester homologue. An explanation given is that the orbitals holding the lone pair on the nitrogen overlaps with the C=O π-bond to give ...
3
votes
1answer
110 views

How do I synthesise this tertiary amide from these 5 compounds?

So basically I'm at a loss as to how to proceed. I started with the idea of converting the primary alcohol into an aldehyde and that is where I stoped. I understand that each substituent of the ...
3
votes
0answers
83 views

Formation of tetrazoles from ketones in Schmidt reaction

Normally in schmidt reaction of ketones, amides are formed however for some reason here further reaction takes place and a tetrazole is formed. Here is my try for this reaction mechanism, (if my ...
-1
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1answer
52 views

Weinreb ketone synthesis [closed]

For this problem, Can I use weinreb ketone synthesis? I found the product but not sure it is the right one If the amide react with either R1-Mgbr or R2-Li, then it produces the ketone?
3
votes
1answer
308 views

Amine vs Amide Solubility

I had a question regarding the solubility of amines and amides. I was looking into the solubility of butanamide and n-Butylamine, and it turns out that whilst butylamine is miscible in water, the ...
0
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0answers
41 views

By what mechanism is ammonia liberated in the Kjeldahl Method of protein determination?

I was looking at the Kjeldahl digestion of proteins, and I very much do not understand the mechanism by which it works. The reaction scheme is as follows: $$\ce{Protein-N + H_2SO_4 ->[K_2SO_4, ...
-1
votes
1answer
104 views

How to evaluate the basicity of molecules? (Ethanamide and Ethanamine, Example) [closed]

Hi there i recently came in a position where was asked to evaluate the basicity of molecules, and managed to understand the heirachy of most molecules, however i couldn't figure out who was more basic ...
2
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0answers
181 views

Reaction of diamines with carboxylic acids to form imidazole

I've recently came across this reaction and my guess is that firstly an amide forms that later reacts with the second amine group. Is this a general reaction? Does it matter if the compounds used are ...
1
vote
1answer
61 views

Reduction of amides with lithium aluminium hydride [closed]

Since $\mathrm{p}K_\mathrm{a}$ of primary amides are close to alcohols, will there be an acid-base reaction between amides and $\ce{LiAlH4}$ besides reduction?
8
votes
2answers
943 views

Can a cyclic amine form an amide?

This is a question from the Cambridge International Examinations October/November 2017 (pdf from papers.gceguide.com, pdf via the Wayback Machine). I need to understand why the secondary amine in the ...
2
votes
1answer
125 views

Can amide bonds fragment in ESI-MS?

Electrospray Ionization Mass Spectrometry(ESI-MS) is a technique in mass spectrometry to get an idea about molecular ion peak. In the ESI-MS spectra of an amide compound, I observed that the molecular ...
0
votes
0answers
220 views

Mechanism for formation of amides from ammonium carboxylate salts

One of the reactions that you can do with a carboxylic acid is to react it with ammonia or an amine, which produces the corresponding ammonium carboxylate salt. When this salt is heated, amide is ...
1
vote
1answer
67 views

Gabriel Phthalamide Reaction

Can we use acid chloride in place of alkyl chloride in Gabriel Phthalamide Reaction? Maybe it can be used as process to synthesize amides.
0
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1answer
2k views

What is the balanced equation of BH3/THF with an amide to form an amine? [closed]

I am doing a green chemistry project as an undergraduate and need the balanced equation to complete the calculations. I cannot find the right information online so any help would be greatly ...
1
vote
1answer
3k views

Reaction between carboxylic acids and amines

Would some be able to explain why when I mix a carboxylic acid, like ethanoic acid, and an amine, say ethylamine, I get ethylammonium ethanoate. But when I mix a bi-functional group carboxylic acid (...
0
votes
1answer
498 views

How is the hydrolysis of amides done in a lab?

I have seen this video about the hydrolysis of amides in order to convert them to a carboxylic acid. I understood how it works but I want to know how would someone physically do it in a lab. I need ...
4
votes
2answers
306 views

Are there amide versions of lactides and lactones?

In my book, I read that Lactides and lactones are cyclic esters which contain two and one ester group in them, respectively. They are formed when $\alpha$-hydroxy; and $\gamma$- or $\delta$- hydroxy ...
2
votes
1answer
186 views

Effects of Groups on the Nucleophilcity of Nitrogen

The reactivity of nitrogen mustards increases with increasing nucleophilicity of the central nitrogen atom. Select the most and least reactive from each of the following groups of nitrogen mustards. ...