12
votes
Accepted
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 ...
- 21.6k
10
votes
Accepted
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 ...
- 25k
9
votes
Accepted
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 ...
- 21.6k
8
votes
Accepted
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
...
- 6,104
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 ...
- 16.4k
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,...
- 28.4k
6
votes
Accepted
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 ...
- 28.3k
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 ...
- 6,218
5
votes
Accepted
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 ...
- 71.1k
4
votes
Accepted
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 ...
- 21.6k
4
votes
Accepted
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 ...
- 53.1k
3
votes
Accepted
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 ...
- 21.6k
3
votes
Accepted
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 ...
- 21.6k
3
votes
Accepted
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. ...
- 39.5k
3
votes
Accepted
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 ...
- 67.3k
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 ...
- 21.8k
2
votes
Accepted
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 ...
- 21.6k
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: ...
- 21.6k
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 ...
- 183
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 ...
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 ...
- 1,909
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 ...
- 4,424
1
vote
Accepted
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 ...
- 1,298
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 ...
- 67
Only top scored, non community-wiki answers of a minimum length are eligible