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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3 votes
1 answer
121 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 ...
5 votes
1 answer
105 views

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 ...
3 votes
0 answers
41 views

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 ...
0 votes
0 answers
34 views

Aromatic nucleophilic substitution of benzyne with amine

All the books say that we can have aromatic nucleophilic substitution by benzyne with strong base like $\ce{NH2-}$. Anyway, I've never seen another base. For example, can we have ARn with 1-...
3 votes
1 answer
176 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 ...
2 votes
1 answer
87 views

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{...
5 votes
2 answers
382 views

Can primary amine be produced using Grignard reagent?

I found a way to produce Secondary Alkyl Amines using Grignard Reagent. Ref: Z. Huang, J. Lv, Y. Jia, Chemistry Select 2016, 1, 5892. DOI: 10.1002/slct.201601464 But I want to know if I can use $\ce{...
18 votes
2 answers
2k views

By what reaction does (–)-sparteine decompose in ambient conditions?

In its pure form (–)-sparteine is an only-slightly-yellow clear, viscous liquid. Yet, after only a week of being kept in dry, normal atmosphere (in a round bottom flask covered by a septa), some of it ...
2 votes
0 answers
45 views

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 ...
3 votes
1 answer
58 views

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 ...
0 votes
0 answers
61 views

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?
5 votes
2 answers
5k views

Reaction of amines with diethyl oxalate (Hofmann amine separation method)

Why does only one molecule of secondary amine react with diethyl oxalate and two molecules of primary amine react with diethyl oxalate? I feel secondary amine also should have reacted similar to ...
1 vote
1 answer
56 views

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 ...
0 votes
0 answers
62 views

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 ...
0 votes
0 answers
45 views

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 ...
5 votes
3 answers
2k views

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

I would like to know if there is a possible route of synthesis that may reduce 3-nitrobenzonitrile A to 3-aminobenzonitrile B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
0 votes
0 answers
21 views

Hoffmann elimination of an amine [duplicate]

The Hoffmann elimination is a reaction that allows an alkene to be obtained from an amine. Mechanistically, it is a three-step reaction. In the first stage, the compound undergoes exhaustive ...
13 votes
2 answers
12k views

Is steric inhibition of resonance or steric inhibition of protonation dominant in o-toluidine?

I wish to know which effect out of steric inhibition of resonance (SIR) or steric inhibition of protonation (SIP) is dominant over the other when comparing basicities of o-toluidine and aniline: ...
1 vote
1 answer
96 views

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{...
2 votes
1 answer
355 views

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....
0 votes
1 answer
111 views

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: ...
5 votes
1 answer
5k views

Is diazotization of o-phenylenediamine to benzotriazole reversible?

Is the synthesis of benzotriazole from o-phenylenediamine with acetic acid and sodium nitrite a reversible process? Not even specifically to o-phenylenediamine but any derivative. Phenylenediamines (...
0 votes
0 answers
30 views

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 ...
-1 votes
1 answer
192 views

What is the product when cyclohexanone reacts with morpholine?

The question asked to find the final product of the reaction between cylohexanone and morpholine. I attempted the reaction which is shown below: I have understood the heat symbol. It simply ...
2 votes
1 answer
165 views

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 ...
0 votes
0 answers
26 views

Why doesn't picolinamide undergo Hofmann rearrangement to form 2-aminopyridine? [duplicate]

I can not find a source that would explicitly state picolinamide undergoes Hofmann rearrangement to form 2-aminopyridine. Does this reaction occur, and if not, why?
4 votes
1 answer
3k views

Why are amines more soluble than ethers in water?

For example, diethyl ether ($\ce{C2H5OC2H5}$) has a limited solubility of $6.05\rm~\frac{g}{100~mL}$ water at $25\rm~^\circ C$. However, diethylamine ($\ce{(C2H5)2NH}$) is a lot more soluble in water. ...
0 votes
1 answer
105 views

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: ...
0 votes
1 answer
52 views

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 ...
4 votes
1 answer
117 views

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 ...
6 votes
1 answer
506 views

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 ...
8 votes
1 answer
296 views

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 ...
4 votes
1 answer
271 views

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?
1 vote
1 answer
256 views

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 ...
4 votes
2 answers
114 views

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 ...
76 votes
7 answers
51k views

Ortho-effect in substituted aromatic acids and bases

When comparing o,m,p-toluidine basicities, the ortho effect is believed to explain why o-toluidine is weaker. But when comparing o,m,p-toluic acid basicities, the ortho effect is stated as a reason ...
-1 votes
1 answer
34 views

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. ...
34 votes
1 answer
33k views

Is the ammonium substituent (-NH3+) really meta-directing in electrophilic substitution?

If we make a resonance structure for the anilinium ion, with positive charge at either the ortho or the para position, we get a pentavalent nitrogen, which is not possible. So, how is the $\ce{-NH3+}$ ...
11 votes
2 answers
606 views

What is the mechanism for iodoform test given by 2-aminoalkanes?

I found 2-aminoalkanes in the list of compounds that give positive iodoform test. I was surprised as they have no keto methyl or methyl carbinol group. Can someone help with the mechanism?
0 votes
0 answers
81 views

Does ammonolysis of primary and secondary alkyl halides proceed through SN2 mechanism?

We know that the first the ammonia acting as nucleophile attack the alkyl halide forming the substituted ammonium salt, but my question is why cannot it proceed through a typical $S_\text N2$ type, ...
3 votes
0 answers
100 views

Is sulphonamide group prone to undergo diazotization?

I wonder if it is not a problem that there is another $\ce{-NH2}$ group in the molecule not connected to aromatic ring and if it can get protonated and react with $\ce{HNO2}$ too, in this case the one ...
7 votes
2 answers
318 views

Why does a larger bond angle correspond to greater s-character?

In trialkylamines $\ce{NR3}$, the $\ce{R}$ alkyl group attached to nitrogen increases the electronegativity of the nitrogen atom. I also found in this question that this happens due to the repulsion ...
13 votes
2 answers
2k views

What is this fluorinated organic substance?

The corresponding author of the paper where this formula was published as appendix passed away. Can someone help me with identifying what is the name of this compound and why have strange zig-zag ...
3 votes
1 answer
2k views

Comparing basic strength order of amines

In the above question I was asked to compare the basic strength order. So I did it like this: The Nitrogen in I and II will not participate in resonance so the only effect it could produce is ...
5 votes
1 answer
1k views

Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?

Compare the acidic strength of o-, m-, p-aminobenzoic acids. I got that meta will be the most acidic as it won't be able to show R+ effect of $\ce{NH2}.$ But among the other two, i.e. ortho and para, ...
4 votes
1 answer
4k views

Mechanism for reaction of NOCl (Tilden reagent) with primary amines

According to The Pearson Guide To Organic Chemistry For The IIT JEE by Atul Singhal, the reaction between $\ce{NOCl}$ and $\ce{CH3CH2-NH2}$ is as follows: $$\ce{CH3CH2-NH2 + NOCl -> CH3CH2Cl + N2 +...
0 votes
1 answer
67 views

Behavior of amines as acids

I came across this question which asked us to find in which alternative does the amine behave as an acid the most: In which of the following reactions does the amine behave as an acid (a) $\ce{(C2H5)...
4 votes
1 answer
760 views

Comparing the basicities of guanidine, acetamidine, benzamine, and dimethylamine

The following compounds were given, and I have to predict their order of basicity: Compound Name Chemical formula A Guanidine $\ce{(H2N)2C(NH)}$ B Acetamidine $\ce{(H3C)(H2N)C(NH)}$ C Benzamidine $...
3 votes
2 answers
11k views

Field Effect and it's effect on basicity on amines

What is the order of basicity between $\ce{Me2NH}$, $\ce{Me3N}$, $\ce{MeNH2}$ in a protic solvent. It has something to do with field effect which I could not understand and could not find anywhere. ...
3 votes
2 answers
215 views

Why do we take two moles of amines in the reaction of amine with an acid chloride?

My textbook states that when reacting an acid chloride (for example, acetyl chloride) with an amine, we need to take two moles of amines because when the $ \ce{-NH-R}$ group displaces the $\ce{-Cl}$ ...

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