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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Preparing an amine from an azide

Is there any mechanism available for reduction of alkyl azides to amines. One of the reactions is conversion by $\ce{Na}$ in ethanol or by $\ce{LiAlH4}$. But how do these proceed? $\ce{LiAlH4}$ will ...
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4k views

Why do methylamine and ethylamine have nearly the same basicity constant?

It is known that ethyl has a stronger inductive effect than methyl. Its positive inductive effect is greater than methyl. Then why does ethylamine has a $\mathrm{p}K_\mathrm{b}$ of $3.35$ and ...
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2answers
304 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. ...
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2answers
89 views

Nitrogen inversion barriers of trimethylamine and N,N-diisopropylmethylamine [closed]

Which would have a smaller nitrogen inversion barrier: $\ce{NMe3}$ or $\ce{N(i-Pr)2Me}?$ I think that $\ce{NMe3}$ should have a smaller inversion barrier as it is less bulky, but data shows otherwise....
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1answer
400 views

Selectivity of diazo-coupling with p-amino phenol

I came across this question and I've been thinking about it since, without being able to find a convincing major product. This question is related to one I found on this site, Diazo Coupling reaction ...
2
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1answer
497 views

Numbering in chlordiazepoxide

The IUPAC name of chlordiazepoxide is given as : 7-chloro-2-methylamino-5-phenyl-3H-1,4-benzodiazepine-4-oxide, but when I started numbering the structure, I am unable to find chlorine on 7th carbon, ...
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2answers
2k views

How to rationalise the basicity order of phenylenediamine?

Why is the basicity of para- > meta- > aniline > ortho- for phenylenediamine? ($\mathrm pK_\mathrm a$: ortho: 9.53, meta: 9.12, para: 7.96) I tried deducing it using resonance and inductive effects ...
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1answer
18k views

Amine group - electron donating or withdrawing group?

Is the amine group a donating or withdrawing group? I think it depends on resonance. If the amine group can participate in resonance, the amine group is inductively donating. Resonance depictions ...
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1answer
78 views

1-propanamine to cyclopropane?

I was solving some questions on amines when I happened to see the below question: propan-1-amine + ($\ce{NaNO2 + HCl}$)= a mixture of products (originally, the mixture in brackets on the ...
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1answer
95 views

Reaction of benzene diazonium salts with different compounds

1. $ \ce{ArN2+Cl-}$ gives addition product with $\alpha,\beta$ unsaturated acids, with decarboxylation being integral part of reaction. For example, $$\ce{ArN2+Cl- + Ph-CH=CH-COOH -> Ph-CH=CH-Ar +...
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1answer
947 views

Why cannot nitrosonium ion attack aniline in electrophylic aromatic substitution?

This is the nitrosonium ion, which is produced by the reaction of $\ce{NaNO2}$ and $\ce{HCl}$: [Image source: Wikipedia] And this is the reaction between aniline and nitrosonium: [Image source: ...
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1answer
157 views

Effects of Groups on the Nucleophilcity of Nitrogen

The reactivity of nitrogen mustards increases with increasing nucleophilicity of the central nitrogen atom. Select the most and least reactive from each of the following groups of nitrogen mustards. ...
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1answer
3k views

Do Grignard reagents deprotonate amines?

Can I add Mg/dry ether to 2,4,6-tribromoaniline followed by $\ce{D2O}$ in order to replace the bromines with deuterium? The reaction I'm proposing is part of a synthetic route as shown below.
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1answer
122 views

Why other benzene derivatives do not undergo nitrosation

Solomon and Fryhle $11 th$ ed : Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction. I agree that if there is a primary or secondary ...
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1answer
648 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 $\ce{H+}$ ...
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2answers
3k views

How to transform an aliphatic primary amine to the corresponding nitro compound?

Could you suggest a reagent or procedure to transform an aliphatic primary amine to the corresponding nitro compound. I know this is a bit backwards of a request because the usual procedure is the ...
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1answer
2k views

Predicting major product of a reaction with nitrous acid

$\hspace{4.5cm}$ For the above reaction I am asked to predict $\ce{X}$, the major product. Of the options given, I thought product (1) would be correct, seeing as how it has the most stable ...
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1answer
556 views

Reduction of amides

The reduction of an amide using LAH yields a primary amine . I looked up the mechanism over here. The mechanism suggests that the final main product (amine) is produced before giving the products a ...
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1answer
444 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.
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1answer
4k views

Mustard oil test for distinguishing between primary aliphatic and primary aromatic amines?

Can the mustard oil test be used for distinction between primary aliphatic and primary aromatic amines? An alkyl isothiocyanate is formed when mustard oil is reacted with a primary aliphatic amine. ...
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1answer
1k views

Distinguishing Test for Organic Compounds

Given the following pairs of samples, how do I distinguish between them? benzamide vs ethanamide ethanoyl chloride vs ethanoic anhydride My Approach: We could easily convert the amides to amines by ...
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1answer
1k views

Is there any reaction between amines and AgNO3?

I found a question in a book about the reaction between $\ce{AgNO3}$ and aromatic/aliphatic amines, but I couldn't find any information about it.
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1answer
3k views

Hofmann Elimination with a Cyclic Amine

What is the final product of this reaction? Here's what I have: Does this look correct? I'm concerned because I'm used to seeing the nitrogen removed from the product (in the cases of primary amines)...
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1answer
542 views

Which is More Stable with Boranes: Amines or Phosphines?

Given borane's ($\ce{BH3}$) LUMO, which of these Lewis bases would have a more stabilizing interaction? In acid bases that means the higher HOMO and lower LUMO equals a stronger dative bond I believe....
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1answer
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Why is the deprotonated form of dopamine more reactive than the protonated/neutral form of dopamine?

See this (from the Wikipedia article on dopamine): Dopamine, like most amines, is an organic base. At neutral or acidic pH levels it is generally protonated. The protonated form is highly water-...
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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 ...
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1answer
4k 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?
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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.
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1answer
449 views

Will Sodium Amide react with Epoxides in the same manner as Grignard Reagents?

I have been unable to find the reaction anywhere on the internet so I'm assuming the answer is no, although I would like an explanation as to why. I can't seem to find any reason why it would not ...
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1answer
24k views

Is the chemical structure of an amide bond (-CONH) or (-CONH2)?

The Dictionary definition of an amide is an organic compound obtained by replacing the −OH group in acids by the −NH 2 group. So from this, I deduced that the bond would be CONH2. But when I ...
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1answer
91 views

What is the name of this organic compound?

The organic compound in question is shown above. This is how I tried to name it: Start from the left hanging $\ce{H_3C}$. $\ce{OH}$ gets the number 2 and $\ce{NH_2}$ gets 6. The lowest numbers ...
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1answer
169 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 ...
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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....
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1answer
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What happens to the amino acid when it is in a solution with the pH of its isoelectric point? (zwitterions)

I am learning about zwitterions and am confused about the following: From what I understand, when amino acids are in their solid form, they exist as zwitterions which is why they have such a high ...
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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. ...
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53 views

Reaction of diamines with carboxylic acids to form imidazole

I've recently came across this reaction and my guess is that firstly an amide forms that later reacts with the second amine group. Is this a general reaction? Does it matter if the compounds used are ...
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127 views

Basicity comparison between pyridine amines and other compounds

In cases 1, 2, 3, the compounds will resonate, thus giving them more stability. Firstly, I want to know whether nitrogen has a +M effect? (due to it having a lone pair of electrons?) In case 1, ...
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Which is more basic: oxaziridine or diaziridine? [closed]

Which is more basic: oxaziridine or diaziridine? Oxaziridine's got one nitrogen and one oxygen as heteroatoms, while in diaziridine there are both nitrogens.
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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 ...
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114 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)...
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How to explain the different regioselectivity of ketones/imines reacting with LDA?

When 1 equivalent of LDA is reacted with, for example, 2-pentanone, you get the thermodynamic (more substituted) product. But when you react butan-2-imine with 1.0 LDA, you receive the kinetic (less ...
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Primary amine versus phosphoramidate reactivity with succinate esters

I have posted two reactions below. The top reaction is well known and occurs readily and near quantitatively (e.g. in protein modification), while the bottom reaction to my knowledge does not exist in ...
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1answer
79 views

Confusion Regarding Nitrogen Inversion

In nitrogen inversion, the lone pair changes its direction continuously. Does this in any way delocalize the charge density on the nitrogen making it less nucleophilic and less basic than another ...
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890 views

Reductive amination in case of secondary amines

When an aldehyde or a ketone undergoes reductive amination when a primary amine is acting,the mechanism follows a pathway through hemiaminal and imine,what happens when a secondary amine is acting on ...
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2answers
2k views

Which is the strongest base among the given anilines?

I am facing difficulty in the following problem. In my view N,N-dimethylaniline 2 should be the strongest base because it has two methyl groups which increases electron density of N and hence it can ...
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641 views

Reductive amination of (protected) 3-Oxopropanenitrile: Will azetidin-2-ol be formed via intramolecular ring closure?

What happens during this reductive amination? I got the first product; the lithium aluminium hydride will reduce the nitrile to an amine. But what about the reductive animation step? As far as I can ...
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1answer
53 views

Gabriel Phthalamide Reaction

Can we use acid chloride in place of alkyl chloride in Gabriel Phthalamide Reaction? Maybe it can be used as process to synthesize amides.
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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!
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2answers
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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 $\ce{NH2}$ ...
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1answer
247 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 ...