Questions tagged [amides]

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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 ...
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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 ...
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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 ...
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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) ...
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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 ...
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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 ...
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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. ...
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Why doesn't picolinamide undergo Hofmann rearrangement to form 2-aminopyridine? [duplicate]

I can not find a source that would explicitly state picolinamide undergoes Hofmann rearrangement to form 2-aminopyridine. Does this reaction occur, and if not, why?
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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-...
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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?
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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1 answer
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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 ...
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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 ...
5 votes
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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 ...
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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?
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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 ...
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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, ...
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1 answer
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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 ...
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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 ...
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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?
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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 ...
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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 ...
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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 ...
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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.
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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 ...
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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 (...
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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 ...
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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 ...
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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 ...
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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. ...
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