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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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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Why is tetramethylammonium hydroxide a stronger base than tri- or dimethyl amine?

Of the following, which compound is the most basic?? $\ce{Me3N}$ $\ce{Me2NH}$ $\ce{Me4NOH}$ $\ce{NaOH}$ Between 1 and 2, 1 is more basic as the 3 methyl groups would produce a +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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847 views

Which is the strongest base relative to ammonia?

I have these bases, ammonia methylamine ethylamine dimethylamine trimethylamine quinuclidine and these two questions: Which is the strongest base relative to ammonia? why? Which conjugate acid ...
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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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54 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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1answer
140 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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229 views

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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114 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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1answer
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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342 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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222 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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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 ...
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329 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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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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6k views

In the condensation reaction of an aldehyde with a hydroxyl amine, why is an oxime formed and not an amide?

Condensation reactions are those that involve removal of a water molecule. When you analyze the reaction between an aldehyde and hydroxyl amine, I don't understand why it's not possible for the acidic ...
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Why amino acids (Zwitterion) become either negative or positive at low and high pH solutions?

The amino acids are Zwitterions. In neutral pH, an Amino acid's amino group has a postive charge and Carboxyl group has negative charge. They cancel each others charge thanks to the $Hydrogen$ that's ...
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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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How can I rationalise the different basicities of cyclohexylamine, piperidine and morpholine?

Compare the basicity of the following compounds: Comparing compounds I and II Since there is no conjugated system, there is no resonance at play and we only have to discuss hyperconjucation ...
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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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Can an amide nitrogen be a hydrogen bond acceptor?

Can $\ce{N}$ (i.e. main chain $\ce{NH}$s of recognised residues in a peptide or protein) be a hydrogen bond acceptor? It is a well known fact that the main chain $\ce{NH}$s can be a hydrogen bond ...
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Decreasing order of basic strength

I need to find the decreasing basicity of the following compounds(I, II, III, IV, respectively): I know that to compare the basic strengths, we need to find the stability of their conjugate acids. ...
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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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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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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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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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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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How to rationalise the resonance structures and hybridisation of the nitrogen in a conjugated amine?

I was given the first structure, and then drew the other 5 resonance structures: First of all, are they correct? ChemBioDraw had some complaints, but as far as I can see there's the same number of ...
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354 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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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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275 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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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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Does aniline react with diazonium ions at C or N?

In the azo coupling of aniline with benzenediazonium cation, I thought of two possible products 1 and 2 that could be formed. However, I can't work out which will be preferred. What would be the major ...
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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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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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What test can be used to differ amide and amine?

For aliphatic amide and amine. I know we can use $\ce{NaOH}$ because amide will give off $\ce{NH3}$, but what will amine yield if we test it with $\ce{NaOH}$?
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Does nitrogen inversion affect the basicity of amines?

If I were to compare the basic strength of 1-azabicyclo[2.2.1]heptane and triethylamine: Can I say that 1-azabicyclo[2.2.1]heptane is more basic than triethylamine because the lone pair of electrons ...
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Selective nitro reduction of poly nitro compounds

Is there any way through which I could selectively reduce one $\ce{NO2}$ group from a dinitro- or trinitro- compound to an amine. I was reading Solomons and Frhyle and it says that m-dinitrobenzene ...
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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). ...
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686 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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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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892 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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Why do Organolithium or Grignard reagents act as nucleophiles and not as bases with aldehydes and ketones

I've read entire Chapter 14: Organometallic Compounds of Francis Carey's "Organic Chemistry" but I still didn't get an answer to my question. Quote from the book: Because of their basicity ...
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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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90 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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543 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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