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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71 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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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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29 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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247 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
54 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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21 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 ...
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1answer
125 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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3answers
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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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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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2answers
751 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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1answer
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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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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
614 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
209 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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1answer
80 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
108 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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305 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
48 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 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 , ...
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1answer
186 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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1answer
88 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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1answer
38 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
455 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
739 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
59 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
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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
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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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401 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 $\ce{CH3}$. ...
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1answer
391 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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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
586 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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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 ...
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Why don't zwitter ions show ortho effect?

I recently came across a statement which said that zwitter ions are an exception to the ortho effect. Is it because the ions attract each other and the -COOH group is brought back into the plane ...
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1answer
94 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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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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1answer
187 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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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 (...
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162 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 ...
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281 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?
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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 ...
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1answer
63 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!
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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. ...