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.
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Basic Hydrolysis of Isocyanates
During the Hoffmann Degradation of amides, in the later part of the mechanism, an alkyl isocyanate intermediate is formed which gets hydrolyzed into primary amines. If a simple hydrolysis occurs by ...
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Why Acid chloride does not react with tertiary amine? (Looking for a suitable reason)
When acid chloride is reacted with a tertiary amine, it basically does not show any reaction. I cannot find a satisfactory reason to this. Everywhere on the internet says, because there's no ...
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Why does the IR-spectrum of N-methyl diethanolamine have two peaks in the 1080-1020 cm-1 area?
I found two peaks in the IR-spectrum of N-methyl diethanolamine in the area of 1080-1020 cm-1, while the IR-spectrum of diethanolamine has only one peak in this area:
(Blue is N-methyl diethanolamine,...
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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 ...
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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 ...
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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]? ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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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 ...
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Why is the lysine side chain more basic?
As per PubChem: $pK_1 = 2.18$; $pK_2 = 8.95$; $pK_3 = 10.53$ at 38 °C, indicating that the side chain amino group is deprotonated at a higher pH, indicating it is more basic. I tried to justify this ...
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Inductive Effect (R-NH3+ and R-NH2)
Textbooks I've read state that R-NH3+ has exhibits a greater -I inductive effect than R-NH2 does.
However, I've also read in places that the + charge in R-NH3+ only represents a formal charge and has ...
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Nomenclature of C6H5CO-O-NH2
How to name the following compound using IUPAC nomenclature? I found benzyl carbamate to be very close to my structure, but couldn't find an exact compound online which matches mine.
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Basicity of pyridine and 2,6-di-tert-butylpyridine
Among pyridine and 2,6-di-tert-butylpyridine, which one would be more basic?
My guess was that since two bulky groups are substituted at ortho position in the latter, it will experience steric ...
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Reason behind benzylamine being a primary amine
Benzylamine is a primary amine. Now a primary amine has the general formula R-NH₂ where R is an alkyl or aryl group. So here R will be equal to $\ce{C6H5CH2}$. But $\ce{C6H5CH2}$ is neither an alkyl ...
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Why is quinuclidine more basic than triethylamine? [duplicate]
I am trying to compare the basic strength of two similar amines
Usually this is done by comparing the relative stability of the ion formed on the protonation of nitrogen's lone pair.
This can be done ...
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Aminium/Ammonium?
Chemdraw names this as 2-carboxyethan-1-aminium. Shouldn't it be ammonium? What's an aminium ion?
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Gabriel Phthalamide Synthesis of 1-Phenylethylamine
I had learnt that due to the nature of the Gabriel synthesis reaction being $S_{N}2$, the alkyl halide used must have a primary alkyl group. However, in an exam (JEE Main 2023), it was mentioned that ...
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Amidine synthesis from nitrile and dimethylamine using n-Buli as a base
I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere.
I have been doing the reaction and I can observe conversion of starting ...
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Does ammonia gas neutralise Hcl salt of amines in dry non polar medium [closed]
I am trying to basify/neutralise the $\ce{HCl}$ salt of amine and other organic compounds by bubbling dry(or semi dry) ammonia gas through a column of the salt suspended in a non polar solvent like ...
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Is it possible to have multiple nitrogen atoms bonded to one carbon atom?
So I was wondering, if we replaced two of the hydrogens in methane with amine groups, would it be a stable compound? What about for R groups of varying size?
Similarly, if I tried to make a compound ...
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Discrepancies in basic strength of different amines
The order of basic strength of ethyl substituted amines is
$\ce{(C2H5)2NH}$ > $\ce{(C2H5)3N}$ > $\ce{(C2H5)NH2}$ > $\ce{NH3}$
Which means secondary amine is more basic than tertiary followed ...
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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 ...
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Lewis Structure of the Guanidinium Ion
In a problem, I was asked to find the Lewis structure of the guanidinium ion $\ce{C(NH2)3}^{+1}$. I followed the following steps which led me to an incorrect structure and I was hoping someone could ...
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Decomposition of aliphatic diazo compounds [closed]
The oxidation of hydrazones produce a diazo compound: orgsyn.org - DIAZOPROPANE.
An intermediate in the Bamford-Stevens reaction is a diazo moiety.
When 2-diazopropane decomposes, does it produce 1-...
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What's the priority order of primary, secondary and tertiary amino groups in IUPAC nomenclature [closed]
It's a really simple question but I didn't get answer to this anywhere. What's the priority order of primary, secondary and tertiary amino groups in IUPAC nomenclature.
For example what would be the ...
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Difference of reactivity between anilines and alkyl amines
Imine synthesis is somewhat common and straightforward, to achieve good yields a good practice is to remove the water formed from the condensation reaction by means of a desiccating agent or a Dean-...
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Will ethyl 2-amino-1H-imidazole-5-carboxylate undergo ester aminlysos with the primary amines of bPEI efficiently in methanol?
I was about to set up the following reaction, but before I do, I wanted to see if anyone has some suggestions or thinks this will not work:
24mmol Nboc protected ethyl 2-amino-1H-imidazole-5-...
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Why does "bis-tris propane" have two pKa values?
Wikipedia gives two pKa values for "Bis-tris propane".
What about bis-tris-propane gives this compound two pKa values where other compounds have only one? How am I to choose which pKa value ...
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Why sulfur dissolved in ethylenediamine turns green?
Davis, R. E., & Nakshbendi, H. F. (1962). Sulfur in Amine Solvents. Journal of the American Chemical Society, 84(11), 2085–2090. doi:10.1021/ja00870a017
I've also done this experiment. But what ...
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Can alkyl halides react with guanidine/guanidino groups?
I wonder how the π delocalization of guanidino groups affects the reactivity of the terminal nitrogens with respect to alkyl halides compared to, say, primary amines?
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comparing basic strength of toluidine isomers [duplicate]
I would like to compare the basicity of ortho and para isomers of toluidine.After comparing the pKb values online the order of basic strength is:
p—toluidine> m—toluidine> aniline> o—...
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Synthesizing octopine from arginine and 2-bromopropionic acid
I am a biologist, and organic chemistry lessons are a distant memory now. I am interested in synthesizing a small amount of octopine. Octopine is a natural molecule resulting from an enzyme-catalyzed ...
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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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What is the pKa value of the nitrogen atoms, specifically the amine groups?
How would you estimate the $\mathrm pK_\mathrm a$ values of the nitrogen atoms in 1,4-dimethyl-1,2,3,4-tetrahydroquinoxaline?
I struggle with it because I am unsure whether to classify them as ...
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Why does alkylamines have a higher boiling point than ammonia?
Here are the boiling points of ammonia and some amines:
$$ \begin{array}{|c|c|}
\hline
\textrm{Substance} & \textrm{Boiling Point} \\
\hline
\textrm{Ammonia} & \pu{-33.34^\circ C} \\
\textrm{...
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Can primary amine be produced using Grignard reagent?
I found a way to produce Secondary Alkyl Amines using Grignard Reagent.
(source: wiley.com)
Ref: Z. Huang, J. Lv, Y. Jia, Chemistry Select 2016, 1, 5892. DOI: 10.1002/slct.201601464
But I want to ...
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How does iodic(VII) acid oxidise amines? [closed]
What happens when 3‐aminobutan‐2‐one undergoes oxidative cleavage with $\ce{HIO4}?$
I'm particularly interested in the amine part. Would the hydroxy and amino groups on the same carbon be stable? Or ...
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Will iron(III) sodium EDTA release its nitrogen into a water medium and become bioavailable to aquatic plants?
I am wanting to create an N-free Hoagland's solution and have discovered a recipe that includes sodium ferric ethylenediaminetetraacetate salt $(\ce{C10H12FeN2NaO8}).$ Will the nitrogen in EDTA ...
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Why isn't the Leuckart reaction used to make (meth)amphetamine?
For example, in Breaking Bad, they synthesize meth from phenylacetone.
Why not just use methylammonium formate, if they already have methylamine?
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Nomenclature of tertiary amine derivative
I’m experiencing difficulties putting together a full name of the tertiary amine. One substituent is propyltrimethoxysilane $\ce{(OEt)3Si-CH2-CH2-CH2\bond{-}}$, and the two others are ...
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How do I understand the IUPAC naming of 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one? [closed]
I'm having trouble understanding the IUPAC naming convention of 9-methyl-3-[(2-methylimidazol-1-yl)methyl]-2,3-dihydro-1H-carbazol-4-one.
It would be great if you can help to breakdown the naming ...
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Mechanism for the synthesis of benzimidazole
I have thought up a mechanism for the synthesis of benzimidazole from o-phenylenediamine and formic acid. I would like to know if it's correct. I have attached it below.
My rationale for the ...
user102173
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Resonance structure with allylic lone pair
Draw the appropriate resonance structure for 5-aminolevulinic acid:
As there is an allylic lone pair, my first arrow goes from the lone pair to form a π-bond, and the second goes from the π-bond to ...
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What is the order of basicity of amines?
My textbook claims that -
Greater is the stability of the substituted ammonium cation, stronger should be the corresponding amine as a base. Thus, the order of basicity of aliphatic amines should be: ...
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Complete mechanism of benzotriazole synthesis from o-phenylenediamine
Does my suggested mechanism for benzotriazole synthesis look correct? Are the arrows for the cyclization in the right place?
Chemdoodle (which I drew this with) makes the curly arrows look a bit weird....
user102173
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Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]
Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject:
First reaction:
Second reaction:
But, I cannot find the reaction mechanism by which ...
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