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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4
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2answers
254 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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1answer
67 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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1answer
127 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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0answers
58 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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0answers
18 views

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 ...
2
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0answers
41 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, ...
5
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0answers
108 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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0answers
22 views

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.
2
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0answers
64 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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1answer
31 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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0answers
947 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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1answer
145 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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0answers
22 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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1answer
57 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 ...
0
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1answer
196 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), ...
4
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3answers
3k views

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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0answers
68 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 ...
5
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3answers
1k views

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 ...
4
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2answers
2k 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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0answers
22 views

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 ...
26
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1answer
4k views

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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0answers
26 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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1answer
38 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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2answers
651 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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1answer
799 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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0answers
19 views

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 ...
4
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1answer
84 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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1answer
211 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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115 views

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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1answer
408 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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1answer
62 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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0answers
134 views

Diazo Coupling reaction with para substituted phenol?

Usually Diazo coupling occurs at para position until the para position is occupied , in which case coupling occurs at ortho position . While solving questions I found in both the cases as shown , ...
3
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1answer
240 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 ...
2
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1answer
97 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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0answers
43 views

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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1answer
40 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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1answer
595 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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1answer
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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1answer
64 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 ...
2
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1answer
73 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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2answers
1k views

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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0answers
487 views

Why is C2H5 a stronger +I group than CH3?

While reading about the basic character of amines, I came across a note which said that $\ce{CH3-CH2-NH2}$ was more stable than $\ce{CH3-NH2}$ as $\ce{C2H5}$ was a stronger +I group than $\ce{CH3}$. ...
4
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1answer
488 views

Why are amidines more basic than amines?

Amidines can be thought of as carboxylic acid derivatives with the carbonyl oxygen replaced by a nitrogen and hydrogen atom; amidines exhibit conjugation. Amidines are more basic (less acidic) than ...
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2answers
258 views

The nomenclature behind “Diacetonamine”

Please explain how the name “Diacetonamine” can be found by looking at the formula: $$\ce{(CH3)2C(NH2)CH2C(O)CH3}$$ Why is it called “Diaceto” if there only one $\ce{-C(O)CH3}$ group?
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1answer
871 views

Why does some coffee smell like urine?

I can smell a urine like odour from some coffees. I don't seem to be alone in this as there are multiple reports on the internet of people having the same experience. I have read from a few posts ...
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2answers
167 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
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1answer
116 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
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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
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1answer
199 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 ...
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0answers
161 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 (...