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Questions tagged [amines]

For questions about amines - organic compounds with a basic nitrogen with a lone pair, also occasionally referred to as derivatives of ammonia. Not to be confused with amides, for which the tag [carbonyl-compounds] is to be used.

4 votes
1 answer
337 views

What are the best conditions for coupling small molecules with EDC?

I want to couple a DNA oligo containing an amino group with another small molecule possessing a carboxyl group. I found protocols for EDC (1-ethyl-3-(3-dimethylaminopropyl)carbodiimide) coupling of ...
0 votes
0 answers
60 views

Conflict: Sandmeyer reaction and Gattermann reaction

So it is known that benzene diazonium chloride when reaction with cuprous(I) chloride would produce a chlorobenzene which is called Sandmeyer reaction. Now for the same salt, if we react it with ...
6 votes
2 answers
570 views

Do alkyl halides with an alpha nitrogen atom undergo SN1 reaction?

Today, in my organic chemistry class, I learnt about the nucleophilic substitution reaction. The notes have stated that: Alkyl halides with $\alpha$ oxygen atom can also undergo SN1 reaction ...
3 votes
0 answers
41 views

How to decide the correct numbering of aminocyclohexenol?

I'm self studying for a university admission exam. So I'm relying fully on online sources to study, but I often get confused because of differing methods. This is one such case: According to this ...
2 votes
2 answers
123 views

How to identify an organic base?

According to the answer key, trimethylamine (iii) and ethanolamine (iv) are considered organic bases, whereas ammonium (i) and acrylamide (ii) are not: From my understanding, an organic base has an ...
3 votes
1 answer
56 views

Iminium formation rate between formaldehyde and secondary amine

Given the significantly more favored hydrate of formaldehyde in the presence of water under neutral conditions, can we say that this is the slow step in iminium formation? Would removing water/working ...
2 votes
1 answer
47 views

What does ‘S/A’ mean in SMARTS pattern when using Chemicalize to draw the chemical structure?

I am still new to the SMARTS annotation. I am wondering what does S/A’ mean on the bond labeling drawn with Chemicalize using SMARTS [!#1]c1n[cH]nc([!#1])c1[!#1]? ...
3 votes
1 answer
197 views

What does ‘(A)’ mean in SMARTS pattern when using Chemicalize to draw the chemical structure?

I am not quite sure what ‘(A)’ could mean for the carbon atom when writing the SMARTS CCN(C)C using Chemicalize to draw the chemical structure below. Can anyone ...
12 votes
1 answer
3k views

What causes rapid nitrogen inversion?

When I asked my teacher whether a nitrogen bonded to 3 unique groups counted as a chiral center, they said that it did not because nitrogen undergoes rapid inversion at room temperature. What causes ...
8 votes
3 answers
7k views

How can I rationalise the different basicities of cyclohexylamine, piperidine and morpholine?

Compare the basicity of the following compounds: Comparing compounds I and II Since there is no conjugated system, there is no resonance at play and we only have to discuss hyperconjucation and ...
3 votes
2 answers
83 views

Why is this amine called this way?

I used a molecule drawing app to name the compound in the image, an amine. The name of the compound is 3-(aminomethyl)hexane according to the app. Shouldn't the name be 2-ethylpentan-1-amine? The ...
2 votes
1 answer
57 views

Frequency to induce nitrogen inversion

I would like to know how to compute the frequency at which nitrogen inversion happens in ammonia gas at STP. The activation energy for such process is 24.2 kJ/mol, therefore I thought that it is ...
0 votes
0 answers
32 views

Which is more nucleophilic: acetamide or aniline?

Which compound will be more nucleophilic, knowing that the electron pair will be more delocalized in the ring for aniline? On the contrary, for the acetamide the electron pair will only be delocalized ...
0 votes
0 answers
38 views

Regarding Hinsberg reagent, potassium salt of primary amine soluble in base become insoluble after acidification?

Distinguish between ethylamine, diethylamine and triethylamine by using Hinsberg's reagent? Ans. This reaction is useful for the distinction of primary, secondary and tertiary amines. (i) Primary ...
6 votes
1 answer
7k views

What is the pKa of methylamine

I completed a practice (not for marks) assignment for an organic chemistry course, and one of the questions asked for the pKa of methylamine. I looked on PubChem, and it gave a result of $10.6$. ...

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