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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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 ...
Ayanokouji Kiyotaka's user avatar
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1 answer
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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 ...
Rajesh Paul's user avatar
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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?
Arbish Ali's user avatar
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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 ...
The Entity's user avatar
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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 ...
InactionBreedsMediocrity's user avatar
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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 ...
Harjot Dhillon's user avatar
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What are the best conditions for EDC coupling of 2 small molecules?

I want to couple 2 small molecules, one is a DNA oligo with an amine group and the other one a small molecule with with a carboxyl group. I found protocols for EDC (1-Ethyl-3-(3-dimethylaminopropyl)...
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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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Enamine formation mechanism. Can't there be alternatives?

I'm studying organic chemistry, more specifically the imines and enamines. I've read about the mechanism of formation of enamine from a generic ketone and a question popped up in my mind. The ...
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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-...
Jack's user avatar
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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 ...
Nicholas DeMarco's user avatar
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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 ...
Dhruv Kaushik's user avatar
3 votes
1 answer
603 views

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 ...
K M F Ruhan's user avatar
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0 answers
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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 ...
Umesh Konduru's user avatar
3 votes
1 answer
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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?
kvanderfluegh's user avatar
3 votes
1 answer
141 views

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 ...
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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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2 votes
1 answer
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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....
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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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Why isn't the aniline hydrolysed in Sanger's protein sequencing method?

Recently I was reading about identifying N-terminal amino acid residues using Sanger's reagent (1-fluoro-2,4-dinitrobenzene). The following image showing the reaction is taken fro Wikimedia Commons: ...
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Ritalin/Concerta/Methylphenidate is an amphetamine?

FIDE (the governing body of international chess competition) says here: The most relevant banned substances for chess are: • Amphetamines – e.g. Adderall, Ritalin (...) Image: I think either ...
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Order of basicity for arylamines and ammonia in gas phase

In aqueous solution, the basicity order is: $\ce{NH3 > Ph-NH2 > Ph-NH-Ph > (Ph)3N}$ What will be the order in gas phase? Following are some considerations: 1- In $\ce{NH3}$, $\ce{N}$ is $\ce{...
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Reaction of primary amine with mixed acid anhydride

Is this reaction $\ce{S_N2}$ (because attack of nucleophile and removal of leaving group are not taking place in a single step)? Which part of anhydride should form the substituted amide? If it is an ...
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4 votes
1 answer
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Which amines show N−N coupling reaction?

We add 1 equivalent of $\ce{KCN}$ followed by catalytic reduction via Lindlar's reagent $(\ce{H2}/\ce{Pt})$ to 4-chlorobenzyl chloride (1). Verify whether the product (P) obtained will undergo an N−N ...
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8 votes
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Hoffman broamide degradation but with alkoxide as base instead of NaOH

Ans.3 I thought it would be similar to Hoffman bromide reaction, and hence the answer (1) but turns out the answer is (3), suggesting the alkoxide attacks the formed amine. But, I couldn't find any ...
tryst with freedom's user avatar
5 votes
1 answer
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Why doesn't hydrolysis of isocyanides take place in basic medium?

Acidic hydrolysis of alkyl isocyanide gives rise to primary amines and formic acid. But alkyl isocyanides do not undergo hydrolysis in basic medium. Why?
Harshit V's user avatar
1 vote
1 answer
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Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?

The major product obtained in the following reaction is: Question source: JEE Main 2019 The molecule shown as product is the official answer given by JEE from the given options. I have written the ...
Jay's user avatar
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2 answers
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Should I do solvent extraction for Buchwald–Hartwig amination?

I am conducting a synthesis involving Buchwald–Hartwig amination. Catalyst is $\ce{Pd2(dba)3},$ ligand is $\ce{P(o-tol)3},$ base is $\ce{Et3N},$ and solvent is toluene. Image below is the proposed ...
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Protein drug conjugate exercise

I am supposed to draw the structure of a derivative of the following structure which could be used to make a protein drug conjugate. And then I should draw the reaction for the protein modification. ...
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6 votes
1 answer
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Formation of Aniline from Chlorobenzene

My textbook says: When chlorobenzene is treated with aqueous ammonia at 473K under a pressure of 60 atmospheres in presence of cuprous oxide or cuprous chloride, aniline is formed. Notice the ...
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