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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52 views

Why is o-nitroaniline not more basic than aniline?

We know from SIR effect (Steric Inhibition of Resonance) that in o-nitroaniline, the nitrogen's p-orbitals will change their plane, causing the conjugation/resonance of its lone pairs to stop. So, the ...
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29 views

How to evaluate the basicity of molecules? (Ethanamide and Ethanamine, Example) [closed]

Hi there i recently came in a position where was asked to evaluate the basicity of molecules, and managed to understand the heirachy of most molecules, however i couldn't figure out who was more basic ...
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When Amines react with Halogenoalkanes, why is it done in ethanolic solution?

Amines react with halogenoalkanes to produce a mixture of secondary, tertiary, and quaternary salts. If free amines are needed (not in their salt form), then you can add a strong base to deprotonate ...
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Reduction of Propanamide with Lithium Aluminium Hydride [duplicate]

When amides are reduced with $\ce{LiAlH4}$ to amines, how come the alcohol functional group is not present- the reduced form of the $\ce{C=O}$ bond. Instead, there is an H present. Is this because $\...
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Comparing basic strength of acetamidine and 2-imidazoline

My approach: Conjugate acids of both molecules have the same number of stable resonance structures. So no conclusion from here. Conjugate acid of 2-imidazoline will have negative inductive on the ...
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81 views

Order of nucleophilicity of Nitrogen atoms in adenine

I recently stumbled upon a question that got me thinking. It goes something like this: Find the major product of the following reaction: There were 3 options given: So it basically aims ...
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44 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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71 views

Which has a greater dipole moment: methylamine or methanol? [closed]

Which has a greater dipole moment: methylamine $(\ce{CH3NH2})$ or methanol $(\ce{CH3OH})?$
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224 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 ...
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140 views

Does aniline react with FeBr₃?

I have read that aniline does not undergo Friedel–Crafts reaction because it complexes with Lewis acid $\ce{AlCl3}.$ Will it also react with $\ce{FeBr3}$ during bromination (to receive a 3-bromo ...
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392 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 the shown compound A to the following product B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
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348 views

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

According to my textbook, the reaction between $\ce{NOCl}$ and $\ce{CH3CH2-NH2}$ is as follows: $$\ce{CH3CH2-NH2 + NOCl -> CH3CH2Cl + N2 + H2O}$$ But how exactly does the reaction proceed? ...
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423 views

What is the pKaH of pyrrole?

I am supposed to say what is more basic and I ran into a problem. I would like to ask if anyone has any idea what is the correct $\mathrm{p}K_\mathrm{a}\ce{H}$ value of pyrrole. I know it is easy to ...
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61 views

What should be IUPAC name of given compound (see image)? [closed]

I think the name should be 1-carbamoylpentane-3-sulphonic acid, but the answer sheet mentions it as 2-carbamoylpentane-3-sulphonic acid: Can anyone please explain why the chain starting with methyl ...
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Alkylation before ring closure?

So, another question from my side. I have been thinking about the folowing reaction: The reaction above exists and was already done on two occasions and reportedly works really well and it seems to ...
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79 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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162 views

Can aniline be made with the method described in Dr Stone?

In Dr Stone, the main character makes aniline by rinsing coal tar with HCl, then mixing in ethyl acetate. See the image below. Is a method like this possible? What is occurring here?
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Is coupling reaction performed in acidic or basic medium? [duplicate]

Why is coupling reaction between aryldiazonium chloride and aniline carried out in a mild basic medium and not under acidic medium? According to me, it can be performed in both mediums.
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68 views

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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32 views

Which of these reactants will not generate this racemic amine?

I understand that in E there is no electrophile the amine can attack, however, I do not understand why A is an answer as well. The amine in A can perform an intramolecular attack on the aldehyde and ...
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2k views

What is Liebermann nitroso test?

From the articles in the internet , I found that there are two reactions which are being called Lieberman nitroso test . One is the test of 2 degree amine in which a 2 degree amine is converted to N -...
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528 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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25 views

Why adenine is an aromatic molecule? [duplicate]

Why is this molecule aromatic? If we include the two π-electrons of the nitrogen on the top $(\ce{NH2})$ the number of π-electrons would be 12, thus it can’t be aromatic.
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66 views

What happens when Hinsberg derivative is added to acidic solution?

The Hinsberg test of $\ce{C5H14N2}$ compound produces a solid that is insoluble in 10% aq. $\ce{NaOH}.$ This solid derivative dissolves in 10% aq. $\ce{H2SO4}.$ Which of the following would best fit ...
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317 views

Which metal ions precipitate in NH4OH? [closed]

From Wikipedia-1, and from an answer here on Stack-Exchange, I can list at least the following elements which will dissolve in aqueous $\ce{NH4OH}$: $\ce{Cr(III), Co(III), Ni(II), Cu(I, II), Zn(II), ...
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Nitration of aniline

(b) Nitration: Direct nitration of aniline yields tarry oxidation products in addition to the nitro derivatives. Moreover, in the strongly acidic medium, aniline is protonated to form the anilinium ...
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109 views

Why is the trimethylammonium group a stronger electron withdrawing group than the nitro group?

I was working on a question that basically boils down to deciding whether the nitro group ($\ce{-NO2}$) or the trimethylammonium group ($\ce{-N+(CH3)3}$) on a benzene ring, is a stronger electron ...
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3answers
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Why does the -OH group in β-naphthol direct the incoming diazonium salt towards the ortho position? [duplicate]

In the following reactions, the major product W is I was doing this question which asks me the product of a diazotisation coupling reaction between diazonium chloride and β-naphthol. I know ...
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4k views

Why are tertiary amines less basic than secondary and primary amines in water than when vapourised?

In gaseous state: $$\ce{(CH3)3N} > \ce{(CH3)2NH} > \ce{CH3NH2} > \ce{NH3}$$ However, when dissolved in water: $$\ce{(CH3)2NH} > \ce{CH3NH2} > \ce{(CH3)3N} > \ce{NH3}$$ My notes ...
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Thermodynamic data related to diazotization reaction

Is there any thermodynamic data available for diazotization of aniline and also for the reduction of the diazonium salt using sodium sulfite? I also want to know the heat of reaction for both the ...
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Why does lemon juice reduce the “fish” odor of sea food — specifically fish?

In studying about amines, I read that lemon juice is also used to wash fish because it reacts with the amines on and in the fish to convert the amines to its salt, just reducing the "fishy smell". I ...
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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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40 views

Efficient way to synthesize poly(alkyl)amine

I am trying to synthesize poly(ethylene-propylene)amine, i.e.: I've read that Reductive Amination is efficient regarding the reaction yield. However, it needs aldehydes to start the reaction. To make ...
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707 views

Can a cyclic amine form an amide?

This is a question from the Cambridge International Examinations October/November 2017 (pdf from papers.gceguide.com, pdf via the Wayback Machine). I need to understand why the secondary amine in the ...
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924 views

Predict the major product of the following reaction with mechanism [closed]

I started to do the problem by coordinating H+ with the lone pair of oxygen then after that I can't proceed .please send the solution by show the detailed mechanism.
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Basicity of subsituted amines [duplicate]

In comparing hydroxylamine, hydrazine, and methylamine for basicity, the order of increasing basicity is hydroxylamine < hydrazine < methylamine. I tried to reason this trend based on electron ...
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93 views

Synthesis of a weinreb amide from an acid

The following shows the conversion of an acid to a weinreb amide: It was taken from the IChO 2015 preparatory problem set problem 23. In this two-step synthesis, I am slighly puzzled by the first ...
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693 views

Histidine vs Lysine

Among the amino acids, histidine and lysine, which is more basic? And why? I tried protonating and checking electronic effects but couldn't reach a satisfactory conclusion.
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Mechanism for formation of amides from ammonium carboxylate salts

One of the reactions that you can do with a carboxylic acid is to react it with ammonia or an amine, which produces the corresponding ammonium carboxylate salt. When this salt is heated, amide is ...
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532 views

Formamide and Hoffmann Bromamide Reaction

I encountered a problem to identify the compound which does not give Hoffmann bromamide degradation reaction. One of the options was formamide, and it was given as the answer. Why can't formamide ...
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78 views

Basic strength of the compound with an conjugate, and an aromatic amine

According to the source of the question answer is c>a>b but shouldn't the order be c>b>a as (a) is attached to a benzene ring and the lone pair will be delocalized?
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Diazo Coupling reaction with para-substituted phenol?

Usually Diazo coupling occurs at para-position unless the para-position is occupied, in which case coupling occurs at ortho-position. While solving questions I found in both the cases as shown, the ...
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1answer
336 views

How does monoethanolamine (MEA) increase pH?

I know pH of a solution increases with increase concentration of $\ce{OH-}$. I'm wondering: when adding MEA, is the $\ce{OH-}$ group from the MEA breaking off, or is it the whole MEA molecule taking ...
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119 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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Relationship between structure and shock sensitivity for branched vs straight hydrocarbons and ammonium ions

In p. 137 of John D. Clark's Ignition! (in the new edition), Clark reports an interesting observation regarding the shock sensitivity of different isomers of alkyls and ammonium salts. Specifically, ...
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49 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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815 views

What is the balanced equation of BH3/THF with an amide to form an amine? [closed]

I am doing a green chemistry project as an undergraduate and need the balanced equation to complete the calculations. I cannot find the right information online so any help would be greatly ...
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1k views

Reaction between carboxylic acids and amines

Would some be able to explain why when I mix a carboxylic acid, like ethanoic acid, and an amine, say ethylamine, I get ethylammonium ethanoate. But when I mix a bi-functional group carboxylic acid (...
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68 views

Aminoethyl or ethylamine?

I was trying to name the above compound which happens to be 3-(2-aminoethyl)-2-methylcyclohexan-1-ol. On my first attempt, I had named it 3-(ethyl-2-amine)-2-methylcyclohexan-1-ol. Which one is ...
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1answer
88 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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