Questions tagged [amides]

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Could polydiazene exist?

I am a bit new to the world of chemistry, and after messing around on ChemSpider, I had a thought. Could a polymer like this exist: Due to VSEPR, it would be shaped pretty weirdly and N-N single ...
shan's user avatar
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1 vote
0 answers
29 views

Does polyamide react with hydrocarbons (group III engine oil) in its thermoplastic state?

I need to form (bend) thermoplastic polyamide hose in rubber jacket to a desired shape. I can use heat gun but I thought for better results I could use heated to 150C group III engine oil (your ...
Yoda's user avatar
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-2 votes
1 answer
47 views

Can I make orthophosphoric acid from sodium dihydrogen phosphate and an acid which I can use to make ethyl iodide?

For my project I needed to di-substitute benzamide with ethyl group at N position to create DEB as a mosquito repellent. The first part of creating benzamide I was able to do, but the second part of ...
N N-DiEthyl Benzamide's user avatar
1 vote
0 answers
56 views

Hydrolysis of polyamides using solid acid catalyst

The neutral hydrolysis of polyamides (eg. nylon 6,6) does not go to completion as the reaction is reversible. You can get around this by carrying out the reaction in an acidic/basic medium. With acid ...
Adam's user avatar
  • 21
0 votes
0 answers
290 views

Why are nitriles less basic than amides?

Like nitriles have a localised lone pair which amides do not have, as their lone pair is delocalised and still amides are more basic. Why? I could not find any satisfactory explanation so please ...
Tasmay Tibrewal's user avatar
3 votes
0 answers
44 views

Compound's reactivity in Hoffman Bromamide Reaction

I already know that the presence of electron donating groups in the soon-to-be migrating group in the Hoffman Bromamide reaction makes the molecule more reactive, but I encountered a question which ...
Dhruv Kaushik's user avatar
0 votes
0 answers
189 views

Why are amides weaker acids than water?

Based on a a recent question I asked on ChemSE, the answer to my question was that amides are weaker acids than water with a typical pKa value of ~20. Although, this answers my question, it got me ...
user avatar
0 votes
0 answers
53 views

How does the second hydrolysis of phthalimide work (hydrolysis of amide)?

In the hydrolysis of Phthalimides we can see two successive hydrolysis of "amides" see ChemLibre for a nice mechanism This is interesting because normally (also according to ChemLibre) ...
Cody Aldaz's user avatar
1 vote
0 answers
92 views

Amides from carboxylic acid and ammonia?

Would it be possible to synthesize amide by simply reacting carboxylic acid with ammonia and then driving off water at higher temperatures? Or would ammonia be also driven off in the process? Google ...
kpeteL's user avatar
  • 53
3 votes
1 answer
272 views

Systematic and preferred names of acetamide

My book says to use carboxamide when it is a carboxylic acid derivative (acyl). Ethanamide $\ce{CH3CONH2}$ is a carboxylic acid derivative, so shouldn’t it be named ethan-1-carboxamide rather than ...
Shashaank's user avatar
  • 352
1 vote
1 answer
191 views

Why is S-alanine acetylated in the synthesis of S-cathinone?

I came across a method of synthesizing enantiomerically pure S-cathinone using S-alanine which is chlorinated to the corresponding acid chloride which is used in a Friedel-Crafts acylation of benzene. ...
Samuel Wango's user avatar
0 votes
0 answers
274 views

Can amide form Schiff base?

Can amide ($\ce{RCONH2}$) form Schiff base? When I searched for it, most papers deal with aliphatic amines. Some paper conducted synthesis with amide-containing compound, but iminization occured at β-...
Krang Lee's user avatar
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-1 votes
1 answer
190 views

What is the mechanism of paracetamol synthesis from N‐acetylsulfanilic acid? [closed]

C can be converted to D with NaOH and heating at 300 °C. What is the mechanism of the reaction?
Sloth123's user avatar
  • 180
1 vote
1 answer
71 views

What is the role of magnesium nitride in ammosamide B synthesis?

The following is a snapshot of the synthesis of ammosamide B from Synarchive: In the final step $\ce{Mg3N2}$ is used to convert esters to amides or amides to amines. What is the mechanism of this ...
Sloth123's user avatar
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6 votes
1 answer
2k views

Acetamide and Nitrous acid Reaction Mechanism

My book says that when acetamide is treated with nitrous acid, ethanoic acid, nitrogen and water are formed but it provides no mechanism. I googled but could not find any mechanism. My guess was that ...
Tahsin Choudhury's user avatar
6 votes
0 answers
269 views

Temperature control and side reactions in PPAA (T3P) couplings

In a lot of procedures for amide couplings (acid + amine) using PPAA, the coupling agent is added to a cooled solution of the acid, amine, and a non-nucleophilic base such as DIPEA. This is done even ...
NotEvans.'s user avatar
  • 17.2k
2 votes
1 answer
650 views

Reacting Grignard reagent with amides

Propene in the presence of $\ce{HBr}$ and $\ce{H2O2}$ gives A. A on reaction with $\ce{Mg}$ in dry ether gives B. B on reaction with acetamide, $\ce{CH3C(O)NH2}$, gives C. In the above question, I ...
Boson's user avatar
  • 115
5 votes
1 answer
872 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 ...
harry's user avatar
  • 1,134
0 votes
0 answers
72 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 ...
Ashish's user avatar
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8 votes
1 answer
980 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 ...
Juan Perez's user avatar
4 votes
3 answers
2k 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 ...
Yushi Li's user avatar
  • 197
4 votes
1 answer
156 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 ...
Chem Geek's user avatar
6 votes
1 answer
699 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 ...
napstablook's user avatar
  • 1,514
-1 votes
1 answer
112 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?
user196092's user avatar
6 votes
2 answers
302 views

How to name aliphatic chain with carboxyl and amide terminal groups?

I know the name 5-carboxyl-2-methylethanoic acid is wrong for the compound $\ce{HOOC-CH(CH3)-CH2-CH2-CH(CH3)-C(=O)-NH2}$ drawn below. Can we just use 5-amido?
Sharbel Damouni's user avatar
3 votes
1 answer
1k 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 ...
Frank's user avatar
  • 71
2 votes
0 answers
104 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, ...
Jabbamanga's user avatar
-1 votes
1 answer
291 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 ...
RockishWood's user avatar
2 votes
0 answers
598 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 ...
jureczeq's user avatar
1 vote
1 answer
152 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?
VMP's user avatar
  • 19
8 votes
2 answers
1k 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 ...
Amar30657's user avatar
  • 301
3 votes
1 answer
437 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 ...
Deepta Chattapadhyay's user avatar
0 votes
2 answers
458 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 ...
S R Maiti's user avatar
  • 5,675
1 vote
1 answer
100 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.
aniketsharma00411's user avatar
0 votes
1 answer
4k 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 ...
mmmmm's user avatar
  • 3
1 vote
1 answer
7k 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 (...
H.Linkhorn's user avatar
0 votes
1 answer
955 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 ...
Andrei Filip's user avatar
5 votes
2 answers
364 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 ...
Abhigyan's user avatar
  • 1,667
1 vote
0 answers
2k views

How to convert lidocaine hydrochloride to lidocaine base?

I'm a hobbyist, no pro. I've got a formulation for a topical anesthetic I'm trying to mimic. It calls for lidocaine, ethoxydiglycol (also known as diethylene glycol monoethyl ether) and a couple of ...
Average Joe's user avatar
2 votes
1 answer
280 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. ...
Nanoputian's user avatar
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