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12 votes
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Can a cyclic amine form an amide?

The heterocycle in this question is indole and is aromatic. This means that the N lone pair is delocalised and not readily available for nucleophilic attack. Think of it as similar in reactivity to a ...
Waylander's user avatar
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10 votes
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Acetamide and Nitrous acid Reaction Mechanism

Amides can be hydrolysed in acidic and basic medium. Nitrous acid facilitates acidic hydrolysis of amides. The reaction can be written as: $$\ce{CH3CONH2 + HNO2 -> CH3COOH + N2 + H2O}$$ The main ...
Nilay Ghosh's user avatar
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9 votes
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Can I synthesize an Amide simply by heating an amine and a carboxylic acid (with a vacuum pump)?

It can be done but it is not a good reaction. From Lundberg et al. [1]: Formally, the amide bond is formed through the condensation of a carboxylic acid and an amine with the release of one ...
Waylander's user avatar
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8 votes
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Are there amide versions of lactides and lactones?

Amide analogue of lactons are lactams, their tautomeric forms are lactims. Citing from the IUPAC Nomenclature of Organic Chemistry (Preferred names 2013): P-66.1.5.1 Lactams and lactims ...
mykhal's user avatar
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8 votes

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

Dimethyl acetamide (DMA) is less susceptible to hydrolysis than ethyl acetate (EA). This statement is true for aqueous acid or base. The infrared (IR) frequency for the carbonyl group of DMA is 1662 ...
user55119's user avatar
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7 votes

On the stabler tautomer in amide-imidic acid tautomerism

The relative stability of the two tautomers (two isomers differing how protons are bound) may be assessed from the equilibrium constant you may formulate for the two. Deriving from above illustration,...
Buttonwood's user avatar
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6 votes
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Amine vs Amide Solubility

The mixing of two compounds is a process which requires consideration of three types of interactions: solute-solvent, solvent-solvent and solute-solute. You make a good argument for the solute-solvent ...
Nicolau Saker Neto's user avatar
5 votes

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

You seem to have got the uses of the compounds right, but could not bring that knowledge together to apply it here. As you said, you first use the Grignard to add a methyl group to D Let's call this ...
Aniruddha Deb's user avatar
5 votes
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Effects of Groups on the Nucleophilcity of Nitrogen

Your analysis of "pulls more electron density away" is a bit too simplistic. Both of them are approximately equally electron-withdrawing via the inductive effect, but in terms of resonance, which is ...
orthocresol's user avatar
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4 votes
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Gabriel Phthalamide Reaction

NO, this is not a viable way to make amides. Phthamide anion will react with acyl halides, but the problem arises with the second step, the removal of the phthalimido group. The usual conditions ...
Waylander's user avatar
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4 votes
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What is the mechanism of paracetamol synthesis from N‐acetylsulfanilic acid?

Finally I find a primary reference by Oae et al.[1] They react benzenesulfonic acid with fused potassium hydroxide using isotopically labelled chemicals. The isotopic labelling results favor a direct ...
Oscar Lanzi's user avatar
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4 votes
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What is the role of magnesium nitride in ammosamide B synthesis?

$\ce{Mg3N2}$ is magnesium nitride. It reacts with $\ce{MeOH}$ to generate magnesium methoxide and ammonia according to online report by Buske [1]. The $\ce{NH3}$ thus generated is acting as ...
Waylander's user avatar
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3 votes
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Could polydiazene exist?

This question touches upon a concept of catenation - an ability of atoms of the same element to make bonds between them that could produce series constituting a chain or ring structure. Something like ...
Fractal's user avatar
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3 votes
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Why is S-alanine acetylated in the synthesis of S-cathinone?

The treatment of N-acetyl-S-alanine with PCl5 gives the acid chloride of the carboxylic acid and converts the N-acetyl group to the imidoyl chloride. This species undergoes classical F-C acylation ...
Waylander's user avatar
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3 votes
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Formation of tetrazoles from ketones in Schmidt reaction

It is true that normally in the Schmidt reaction of ketones, amides are formed as the major product (Ref.1). However, the products from the Schmidt reaction is highly depeends on the conditions used. ...
Mathew Mahindaratne's user avatar
3 votes
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Reaction between carboxylic acids and amines

You have a false dichotomy. Diamines and diacids can form salts with doubly charged anions and cations. Sadly, simply searching SigmaAldrich’s catalogue for the phrase diammonium did not turn up any ...
Jan's user avatar
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2 votes

Can amide bonds fragment in ESI-MS?

Yes, amide bonds can fragment during electrospray ionization. Intentional fragmentation in a collision cell Amide bonds are intentionally fragmented in mass spectrometers all the time, during ...
Curt F.'s user avatar
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2 votes

Mechanism for formation of amides from ammonium carboxylate salts

The question is about mechanism of amidation not from R-NH2/R'-COOH but from their salt R-NH3+/R'-COO-. The former is well known and the only mechanism of amidation. The salt R-NH3+/R'-COO- is always ...
Jin Chul Jung's user avatar
2 votes
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How is the hydrolysis of amides done in a lab?

The answer, as with so much chemistry, is it depends. What substrate are you hydrolysing, is it a primary, secondary or tertiary amide? What else is in the molecule that you want to preserve? Both ...
Waylander's user avatar
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2 votes

Reduction of amides with lithium aluminium hydride

Not according to the commonly accepted mechanism here The first step is The nucleophilic H from the hydride reagent adds to the electrophilic C in the polar carbonyl group of the ester. Note: ...
Waylander's user avatar
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2 votes

Could polydiazene exist?

A magnesium nitride compound with the empirical formula $\ce{MgN4}$, having polymerized nitrogen chains, is known under high pressure. Under about 50 GPa pressure magnesium can form a pair of ...
Oscar Lanzi's user avatar
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2 votes

Reacting Grignard reagent with amides

In the reaction that you have mentioned above, the reaction essentially stops after the reaction has taken place in a 1:1 ratio. That is because the electrophilicity of the polar bond of the acid ...
Siddhant's user avatar
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2 votes

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

No, amido will not work here. According to IUPAC 2013, P-35.3 COMPOUND SUBSTITUENT PREFIXES P-35.3.1 Names of compound prefixes derived from suffixes or functional parent compounds may be formed by ...
Aditya Kumar Panda's user avatar
1 vote

How to identify an organic base?

Organic base has an atom with a lone pair of electrons. This statement is not true considering the fact that the lone pair of the compound may be in resonance. Consider the example of a carboxylic ...
Nightwing's user avatar
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1 vote
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How to identify an organic base?

Organic bases are just organic compounds which act as bases. These primarily include amines. Compound two is an amide. Amides are more acidic than amines, and they very rarely act as organic bases. ...
The Fright Of The Night's user avatar
1 vote

Systematic and preferred names of acetamide

The first thing to do when constructing a systematic name is to find the parent structure - be it a cycle, or in this case an acyclic chain. You choose the parent structure with the most skeletal ...
user213305's user avatar
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1 vote

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

You have correctly identified the principal characteristic group as acid, which is expressed as suffix. The amide can be expressed as various prefixes. The corresponding subsection in the current ...
Loong's user avatar
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1 vote
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How to evaluate the basicity of molecules? (Ethanamide and Ethanamine, Example)

So, there are many factors that affect acidity or basicity of a compound, the main factors being bond electronegativities and resonance structures. However, I believe you are correct in assuming that ...
mpprogram6771's user avatar
1 vote

Are there amide versions of lactides and lactones?

Cyclic amides are known as lactams. They can be a β-lactam which is a 4-membered ring, a γ-lactam which is a 5-membered ring, a δ-lactam which is a 6- membered ring, an ε-lactam which is 7-membered ...
Isaac Lai's user avatar

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