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.

Filter by
Sorted by
Tagged with
-1
votes
2answers
237 views

Feasibility of Electrophilic attack on the Nitrogen over the Phenyl ring of Aniline

I have learnt that the '-NH2' substituent attached to the phenyl ring, owing to the substitutent's highly positive mesomeric effect, activates the phenyl ring quite a lot for Electrophilic Aromatic ...
2
votes
1answer
136 views

NMR of phenylethane amine

I did an undergraduate experiment and could use some help in interpreting the $\ce{^1H}$ NMR spectra. This was the task: About $\pu{5-10mg}$ (1-2 drops) distilled amine is weighed in a NMR tube. Put ...
2
votes
0answers
36 views

Can catecholamines be quantified by HPLC-MS/MS at high pH?

It seems that most HPLC-MS/MS methods used for quantitation of catecholamines (epinephrine, norepinephrine and dopamine, specifically) operate at low pH (commonly 3.0), and therefore demand the ...
4
votes
1answer
216 views

Can enamines be formed from α,β-unsaturated ketones?

This question was a result of discussion form here: α,β-unsaturated carbonyl compounds and alkyl addition The reaction below (condensation of cyclohexenone with a secondary amine) does not yield any ...
1
vote
0answers
174 views

Why ammonium salts can not undergo substitution

Why is ammonium salt, such as RNH3+, can not react with nucleophiles like HI to give RI and NH4+? The reaction is pretty much like the substitution of alcohol in acid condition. In my opinion, NH3 (...
3
votes
0answers
213 views

On what factors does amine inversion depend

What factors promote amine inversion? Like bulky groups around the nitrogen atom or less sterically crowding groups? Are there any other factors that affect amine inversion? Does the ...
1
vote
0answers
326 views

Why can tertiary amines not show chirality?

Why is a tertiary amine with three different substituents not chiral? Doesn't the lone pair represent a fourth, different substituent?
-1
votes
1answer
116 views

Polyamides Reaction mechanism

I already know that polyamides are made through condensation polymerisation with a carboxylic acid and an amine. But how exactly does the mechanism work? If the reaction takes place in acid for ...
1
vote
1answer
67 views

How would 2-(chloromethyl)-1-methylpyrrolidine recyclize into 3-chloro-1-methylpiperidine with only water?

My Attempt I always get thrown off by mechanisms with just water as a solvent. I've attached my work as far as I could get but I'm not sure where to go from there. Thank you!
2
votes
2answers
259 views

Out of the given reagents, find the ones to be used to convert benzene to p-aminophenol

$\ce{Br2/FeBr3}$ $\ce{CH3Cl/AlCl3}$ $\ce{KMnO4}$ $\ce{HNO3/H2SO4}$ $\ce{NBS}$/hv $\ce{NaOH}$ $\ce{Sn/HCl}$ $\ce{NH4SH}$ $\ce{NaBH4}$ I'm able to get the amino group onto the ring by using 4 and 7. ...
0
votes
1answer
53 views

Solvents for monoalkylations?

Just beginning to grasp this. Betaphenylethylamine to n-methyl-b-pea. Can I use water instead of DMSOesque solvent in regards to cesium carbonate/hydroxide monohydrate? Also are molecular sieves ...
1
vote
1answer
4k views

Reaction of primary nitroalkane with nitrous acid

I was reading the reaction of primary nitroalkane with nitrous acid. I read this reaction Another mechanism which I saw: I am now confused whether the first mechanism occur or the second one.I ...
1
vote
1answer
963 views

What happens to a quaternary ammonium cation at a pH above its pKa?

I am working with a lipid and I have firm reasons to believe that its pKa is around 8. This lipid is a cationic lipid where the nitrogen is a quaternary amine with two lipid chains and two methyl ...
1
vote
1answer
562 views

Strong activation of phenoxide ion compared to others

I was told that that in phenoxide ion, benzene ring is very strongly activated. The order my teacher told me was phenol < amine < 2 degree amine < 3 degree amine < phenoxide (for ...
6
votes
2answers
307 views

What are the IUPAC names for singly- and doubly-protonated piperazine?

If ammonia, $\ce{NH3}$, is protonated, it becomes ammonium: $\ce{NH4+}$. If piperidine is protonated, it becomes piperidinium: If piperazine is protonated once, what does it become? By analogy, I ...
4
votes
2answers
204 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 ...
2
votes
1answer
4k views

Which one is more basic: acetamide or aniline? [duplicate]

Which one is more basic: acetamide or aniline? I had approached the question by protonating both of the compounds. Then I judged them on the basis of the stability of the corresponding conjugate acid....
1
vote
2answers
493 views

Acid in Imine Formation

Why is a strong acid like $\ce{H2SO4}$ used for imine formation here instead of a weaker acid like TsOH? I thought that if the pH was too low, the amine molecule would get protonated to an ammonium, ...
2
votes
1answer
2k views

Comparison of basic strength of benzylamine and ammonia

According to me, ammonia should be the stronger base for two reasons: $\ce{-C_6H_5}$ group shows $-I$ effect, due to which electron density on $\ce{N}$ atom of benzylamine decreases steric hindrance ...
5
votes
1answer
2k views

Reaction of amines with diethyl oxalate (Hofmann 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 ...
10
votes
1answer
250 views

What is the preferred IUPAC name of hexamethyldisilazane?

Hexamethyldisilazane (HMDS, $\ce{(SiMe3)2NH}$) and its conjugate base hexamethyldisilazide (as the Li/Na/K salt) find wide use in organic chemistry. In my quest to only use preferred IUPAC names in ...
6
votes
1answer
5k views

Product of primary amine and acid anhydride

How does an acid anhydride react with a primary amine? I thought it'll be some sort of condensation reaction, so I made the product by removing a water molecule and got a cyclic product. However, the ...
7
votes
2answers
6k 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
0answers
704 views

Why is ethanol used in catalytic reduction of nitro group to an amine? [closed]

$$\ce{R-NO2 +C2H5OH + H2 (g)->[Pt/Pd/Ni] R-NH_2}$$ The above equation represents catalytic reduction of nitro group to amine. What is the role of ethanol in it? I understand that $\ce{Pt/Pd/Ni}$ ...
1
vote
0answers
3k views

Why is phenol more acidic than aniline?

I find that there are two contradicting factors at play here: 1) On removing proton, negative charge on oxygen is more stable than it is on nitrogen (because of greater electronegativity of oxygen). ...
1
vote
1answer
384 views

Why do the amino groups in EDTA deprotonate first, in contrast to amino acids?

We know that in amino acids, carboxylic acid groups deprotonate first than the amine groups. For example, in alanine, $\mathrm{p}K_\mathrm{a,\ce{COOH}} = 2.34$, $\mathrm{p}K_\mathrm{a,\ce{NH3+}} = 9....
4
votes
1answer
445 views

Can aniline autodeprotonate?

I had an argument with an assistant in my lab, as he stated that in a hypothetical reaction two aniline molecules could react in a way, that one takes a proton off of the other one, thus creating a $\...
2
votes
0answers
109 views

Electron donating ability of substituted amines on aromatic ring

How would you arrange the conjugate bases of the following amines in order of electron donating ability as EDGs as substituents on an aromatic ring? $\ce{NH3}$, $\ce{(C2H5)(C2H4CN)NH}$, $\ce{(C2H4OH)...
1
vote
1answer
6k views

Hoffman's Isocyanide test: How does addition of concentrated HCl degrade the isocyanide formed?

This question is regarding a laboratory procedure followed for Hoffman's Isocyanide test (also known as the "Carbylamine test") I've been taught that the isocyanide formed in this reaction is highly ...
1
vote
2answers
5k views

Does the amine group participate in resonance in aniline? [duplicate]

When we draw resonance structures of aniline, 8 electrons participate in resonance, making it antiaromatic. But in our school textbook, it is said to be aromatic. Does the lone pair of $\ce{NH2}$ ...
3
votes
0answers
109 views

effect of different groups on Amine inversion

I know different groups attached to the nitrogen atom affect the amine inversion barrier, but is it due to steric factors or orbital interaction factors, eg. $\ce{(i-Pr)2NMe}$ vs $\ce{NCl3}$.
5
votes
1answer
189 views

Amine Inversion and Paramagnetism

In amine inversion, there is a planar $sp^2$ intermediate. The electron pair transferred from the blue lobe to the red one during the inversion. It is natural to assume, for a layman like me, that ...
-1
votes
1answer
613 views

Safest Methylating Agent

I am planning on doing some synthesis in the near future and due to safety purposes I am looking for a methylating agent that is both effective and safe. The substrate is a deprotonated amine and the ...
4
votes
1answer
1k views

Byproducts of LiAlH4 reduction of amides

I know that $\ce{LiAlH4}$ is able to reduce amides into amines, e.g. benzamide into benzylamine. However, I am unsure what other by-products are formed as a result. $$\ce{LiAlH4 + C6H5CONH2 -> ...
1
vote
0answers
364 views

How to find out which organic molecules would be good electron acceptors/donors on a GaAs semiconductor surface [closed]

I'm a physicist in way over my head. I have a list of organic molecules to investigate, all common aldehydes and amines. My supervisor wishes to know which of these molecules would be good electron ...
5
votes
2answers
544 views

Reduction of 1,4-benzoquinone in the synthesis of 1,5-diazocane

Synthesize 1,5-diazocane using only benzene as a source of carbon atoms, and ammonia as the only source of nitrogen atoms. My attempt: Noticing that the target compound has split the benzene ring, ...
1
vote
1answer
213 views

Organic nomenclature of substituted diamines

Nomenclature of substituted amines is done with the N-locants, with the N being used to indicate that a group is connected to the methyl group. I was wondering, therefore, on how to properly name a ...
1
vote
0answers
174 views

Why have citric acid only a denticity of 3 and tartaric acid of only 2?

Why can't the hydroxyl-groups in citric acid (denticity 3) or in tartaric acid (denticity 2) contribute to the denticity, as there are doing it in aminoethylethanolamine (denticity 3) Why do the ...
4
votes
1answer
1k views

pKa of imidazoles

I was looking for the $\mathrm{p}K_\mathrm{a}$ of imidazole and found this $\mathrm{p}K_\mathrm{a}$ table [1]: \begin{array}{ll} \text{Compound} &\mathrm{p}K_\mathrm{a} \\ \hline \text{...
5
votes
0answers
93 views

How to theoretically predict thermodynamic stability?

Let's say we have $\ce{CH3-NH2}$ undergoing Hoffman's exhaustive methylation with $\ce{CH3-Cl}$. In which case side reactions such as $\ce{CH3-NH2 + CH3-NH2 -> CH3NHCH3 + NH3}$ would also occur. ...
2
votes
1answer
429 views

Aromatic and aliphatic amines

Is benzylamine $\ce{C6H5CH2NH2}$ an aromatic or aliphatic amine? I've tried searching for it however different sources have conflicting information.
2
votes
1answer
615 views

Mechanism of Hofmann Rearrangement Reaction

In the Hofmann Rearrangement Reaction (in basic medium), when $\ce{RNH-}$ ion is produced, why does it not attack $\ce{Br2}$ or take $\ce{H+}$from the amide itself? Also, why does it take $\ce{H+}$ ...
0
votes
1answer
94 views

Which group is more suitable for metal nanoparticles functionalization? [closed]

I have synthesized bimetallic nanoparticles (gold core with a silver shell). I have two choices for functionalizing them, through thiol group or amine group. Which of them is more attracted to this ...
1
vote
0answers
74 views

Can amines in acidic medium last for long?

I have been thinking of a situation where amines are kept in moderately-to-highly acidic media. In such a case, the amines would assume the protonated forms: $$\ce{RNH2 + H3O+ <=>> RNH3+ + ...
4
votes
1answer
488 views

Why is ammonium chloride rather than an alkylammonium chloride salt the product of nucleophilic substitution of a chloroalkane by ammonia?

My textbook said that when an excess of ethanolic ammonia is heated with a haloalkane ($\ce{R-X}$) one should give the products as being $\ce{R-NH2}$ and $\ce{NH4Cl}$ as opposed to $\ce{RNH3Cl}$. I ...
2
votes
1answer
3k views

Why is p-toluidine more basic than m-toluidine?

https://en.wikipedia.org/wiki/Toluidine In m-toluidine the $\ce{CH3}$ group is closer to $\ce{N}$ so shouldn't that increase the electron density on $\ce{N}$ and make it a stronger base?
3
votes
1answer
1k views

Are amines amphoteric?

An amine can react with an acid just like any other base to form a salt: $$\ce{RNH2 + HCl-> RNH3+ Cl-}$$ According to my textbook (unreliable), amines also react with bases just like any other ...
1
vote
1answer
3k views

How does aqueous ammonia react with hypochlorous acid in water?

Here is what I have so far: $$\ce{NH3 + HOCl -> NH2Cl + H2O}$$ Since ammonia reacts with hypochlorous acid to form the chloramine $\ce{NH2Cl}$. But I don't know if this is correct.
13
votes
3answers
271 views

Mechanism for Amino-Imidazole Ring Fission

A reaction I've tried several times in the past is the hydrogenation of nitroimidazole derivative shown below. The amino product is extremely unstable and rapidly decomposes. This instability is ...
4
votes
1answer
993 views

What would happen if Hofmann bromamide reaction is carried out in Br2 and KOD?

What would happen if Hofmann bromamide reaction is carried out in Br2 and KOD ? I already know the mechanism the question is the water molecules that is attacked by the isocyanide is it already ...