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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23 views

What is the order of basicity of amines?

My textbook claims that - Greater is the stability of the substituted ammonium cation, stronger should be the corresponding amine as a base. Thus, the order of basicity of aliphatic amines should be: ...
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121 views

Complete mechanism of benzotriazole synthesis from o-phenylenediamine

Does my suggested mechanism for benzotriazole synthesis look correct? Are the arrows for the cyclization in the right place? Chemdoodle (which I drew this with) makes the curly arrows look a bit weird....
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Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]

Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject: First reaction: Second reaction: But, I cannot find the reaction mechanism by which ...
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Why doesn't picolinamide undergo Hofmann rearrangement to form 2-aminopyridine? [duplicate]

I can not find a source that would explicitly state picolinamide undergoes Hofmann rearrangement to form 2-aminopyridine. Does this reaction occur, and if not, why?
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90 views

Why isn't the aniline hydrolysed in Sanger's protein sequencing method?

Recently I was reading about identifying N-terminal amino acid residues using Sanger's reagent (1-fluoro-2,4-dinitrobenzene). The following image showing the reaction is taken fro Wikimedia Commons: ...
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129 views

Ritalin/Concerta/Methylphenidate is an amphetamine?

FIDE (the governing body of international chess competition) says here: The most relevant banned substances for chess are: • Amphetamines – e.g. Adderall, Ritalin (...) Image: I think either ...
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1answer
69 views

Order of basicity for arylamines and ammonia in gas phase

In aqueous solution, the basicity order is: $\ce{NH3 > Ph-NH2 > Ph-NH-Ph > (Ph)3N}$ What will be the order in gas phase? Following are some considerations: 1- In $\ce{NH3}$, $\ce{N}$ is $\ce{...
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38 views

Reaction of primary amine with mixed acid anhydride

Is this reaction $\ce{S_N2}$ (because attack of nucleophile and removal of leaving group are not taking place in a single step)? Which part of anhydride should form the substituted amide? If it is an ...
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1answer
112 views

Which amines show N−N coupling reaction?

We add 1 equivalent of $\ce{KCN}$ followed by catalytic reduction via Lindlar's reagent $(\ce{H2}/\ce{Pt})$ to 4-chlorobenzyl chloride (1). Verify whether the product (P) obtained will undergo an N−N ...
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285 views

Hoffman broamide degradation but with alkoxide as base instead of NaOH

Ans.3 I thought it would be similar to Hoffman bromide reaction, and hence the answer (1) but turns out the answer is (3), suggesting the alkoxide attacks the formed amine. But, I couldn't find any ...
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150 views

Why doesn't hydrolysis of isocyanides take place in basic medium?

Acidic hydrolysis of alkyl isocyanide gives rise to primary amines and formic acid. But alkyl isocyanides do not undergo hydrolysis in basic medium. Why?
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133 views

Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?

The major product obtained in the following reaction is: Question source: JEE Main 2019 The molecule shown as product is the official answer given by JEE from the given options. I have written the ...
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Should I do solvent extraction for Buchwald–Hartwig amination?

I am conducting a synthesis involving Buchwald–Hartwig amination. Catalyst is $\ce{Pd2(dba)3},$ ligand is $\ce{P(o-tol)3},$ base is $\ce{Et3N},$ and solvent is toluene. Image below is the proposed ...
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Protein drug conjugate exercise

I am supposed to draw the structure of a derivative of the following structure which could be used to make a protein drug conjugate. And then I should draw the reaction for the protein modification. ...
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339 views

Formation of Aniline from Chlorobenzene

My textbook says: When chlorobenzene is treated with aqueous ammonia at 473K under a pressure of 60 atmospheres in presence of cuprous oxide or cuprous chloride, aniline is formed. Notice the ...
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54 views

Does ammonolysis of primary and secondary alkyl halides proceed through SN2 mechanism?

We know that the first the ammonia acting as nucleophile attack the alkyl halide forming the substituted ammonium salt, but my question is why cannot it proceed through a typical $S_\text N2$ type, ...
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Is sulphonamide group prone to undergo diazotization?

I wonder if it is not a problem that there is another $\ce{-NH2}$ group in the molecule not connected to aromatic ring and if it can get protonated and react with $\ce{HNO2}$ too, in this case the one ...
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273 views

Why does a larger bond angle correspond to greater s-character?

In trialkylamines $\ce{NR3}$, the $\ce{R}$ alkyl group attached to nitrogen increases the electronegativity of the nitrogen atom. I also found in this question that this happens due to the repulsion ...
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55 views

Behavior of amines as acids

I came across this question which asked us to find in which alternative does the amine behave as an acid the most: In which of the following reactions does the amine behave as an acid (a) $\ce{(C2H5)...
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113 views

What is the product when cyclohexanone reacts with morpholine?

The question asked to find the final product of the reaction between cylohexanone and morpholine. I attempted the reaction which is shown below: I have understood the heat symbol. It simply ...
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2answers
98 views

Why do we take two moles of amines in the reaction of amine with an acid chloride?

My textbook states that when reacting an acid chloride (for example, acetyl chloride) with an amine, we need to take two moles of amines because when the $ \ce{-NH-R}$ group displaces the $\ce{-Cl}$ ...
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1answer
192 views

Comparing the basicity of heterocyclic amines

Compare the relative basicity of the following amines. I know that the higher the electron density on the nitrogen the higher will be its basicity. So here’s my take on each option. (a)The Nitrogen ...
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Procedure for laboratory synthesis of tertiary amines [closed]

I am having difficulty finding a procedure for making tertiary amines in the lab, any is fine but I am specifically interested in tributylamine.
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198 views

Comparing acidic strengths between benzylammonium ion and phenol

Question Compare the acidic stengths between benzylammonium ion and phenol. I first tried to remove the H+ ion from both of them and tried to compare the relative stabilities of resulting conjugate ...
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Safety concerns (Cyanide): Dicyandiamide + Polyamine condensation reaction

I am attempting to synthesize a poly-amine polymer by condensation between dicyandiamide (also known as cyanoguanidine and dicyandiamine) and diethyltriamine. The polymer is a kind of dye fixative ...
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37 views

Which one will be the major product when multiple sites for lone pair attack is available?

I have been asked to find the major product of the following reaction: Clearly, there are two possible sites for the lone pair of $\ce{NH_3}$ to attack, and thus two possible products. The carbon ...
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102 views

Can the guanidinium ion give stable N-nitrosamines under mild metalworking conditions?

Can the guanidinium ion react with inorganic nitrite under mild basic metalworking conditions ($\mathrm{pH\ 8 - 10}$ and temperature $\lt \pu{70^\circ C}$) to give stable N-nitrosamines? Usually, the ...
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1answer
190 views

Is there a way to convert aniline to phenol without diazotizing it?

I am a high school student and while reading about reactions on amines, I was trying to figure out a way to convert aniline $(\ce{C6H5NH2})$ to phenol $(\ce{C6H5OH})$ without diazotizing it with ...
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826 views

Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?

Compare the acidic strength of o-, m-, p-aminobenzoic acids. I got that meta will be the most acidic as it won't be able to show R+ effect of $\ce{NH2}.$ But among the other two, i.e. ortho and para, ...
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2answers
297 views

Why IUPAC name this amine is written as 2-methylpropan-2-amine and not as 2,2-dimethylethanamine? [closed]

Why IUPAC Nomenclature of following amine is written as 2-methylpropan-2-amine and not as as 2,2-dimethylethanamine?
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74 views

Is tautomerism in ketimines possible?

In a reaction between an aliphatic primary amine and a ketone, I could expect a ketimine as a product or intermediate. My question regards tautomerization of this intermediate: has tautomerization ...
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444 views

While treating 4-aminophenol with acetic anhydride why does the reaction stop at Paracetamol and does not undergo esterification with acetic acid?

This needs a little background so I will be showing you a question from one of my Organic Chemistry problem books:- Now, the book shows the answer as Option (c) which is Paracetamol. I tried to work ...
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186 views

Conversions in amines

We have to find A, B, C, D, E, F, G, H. I got C is acetophenone and D is benzoic acid and further I got what are E,F,G,H I am just a bit confused in A and B please any hints.. Edits : C is ...
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What's the reason that alkanolamines change their color at storage?

What's the reason that alkanolamines (e.g. monoethanolamine, diethanolamine, triethanolamine) of technical purity change their color (from colorless over yellowish to red-brown) at storage? Is it ...
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158 views

How are diazonium salts prepared without self coupling

While preparing diazonium salts, what prevents the freshly formed diazonium salt from reacting with the still unreacted amines left in the solution and perform diazo coupling? If this happened then ...
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1answer
130 views

Laboratory and commercial preparations of aniline other than reduction of nitroarenes [closed]

Till now I could only find one laboratory preparation of aniline, i.e. reducing nitrobenzene with $\ce{Sn}$ and concentrated $\ce{HCl}$. I'm confused if Hofmann degradation is only commercial. I'd ...
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291 views

Why is N,N,2,6-tetramethylaniline less basic than N,N,2-trimethylaniline?

According to me, N,N,2,6-tetramethylaniline should be more basic than N,N,2-trimethylaniline due to more steric inhibition to resonance, but the answer is given opposite. What is the reason for that?
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How to predict amine donor in biochemical reactions (whether glutamine or aspartate)?

In biochemical reactions amine $(\ce{-NH2})$ transfer is done in multiple pathways (e.g. urea cycle, purine biosynthesis etc.). In many of the situations glutamine donates amine group (e.g. xanthosine ...
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1answer
224 views

Regioselectivity in coupling reactions of α-naphthol

I have seen in the following reaction of azo coupling where coupling takes place at position 4 of $\alpha$-naphthol. Now the electron density accumulation is similar at both position $4$ as well as $...
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Alternate pathway of Gabriel synthesis to prepare secondary amine

Can modifying the Gabriel synthesis, which is generally restricted to synthesis of primary amines, be used to synthesise secondary amines? I have attached my idea regarding the synthesis (the final ...
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Can the inner amine groups of Bacteriopheophorbide A become positively charged in aqueous solutions without the use of very strong acids?

In an attempt to calculate the pKa of the carboxylic acid group of Bacteriopheophorbide A (BPheo, Pubchem), I generated the structure in MarvinSketch (ChemAxon product) and I came across an ...
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569 views

Amine vs Amide Solubility

I had a question regarding the solubility of amines and amides. I was looking into the solubility of butanamide and n-Butylamine, and it turns out that whilst butylamine is miscible in water, the ...
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47 views

Feasibility of phenyl migration

I am learning the fundamentals of organic chemistry, here is the reaction which got me stumbling me for hours, in the below reaction i could see that the amine group would get converted into diazonium ...
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184 views

Metamerism in amines [duplicate]

I came across a question where $\ce{R-CH2-NH2}$ and $\ce{R-NH-CH3}$ are considered as functional group isomers but not as metamers. If I'm not wrong, metamers compounds which have same molecular ...
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633 views

Do amines or alcohols have stronger intermolecular hydrogen bonds?

Which has stronger hydrogen bonding, $\ce{CH3OH}$ or $\ce{CH3NH2}$ I think it comes down to which has more dominance; number of hydrogens, number of lone pairs, or electronegativity.
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247 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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95 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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54 views

Benzylation and acetylation of amines and alcohols

Question Attempt Since the nitrogen site is more nucleophilic it should react first. But still Oxygen can react and hence I believe A should be right. But the book says C. Where did I go wrong? ...
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172 views

Purification of primary amines using Schiff base immobilization

I want to purify all primary amines containing compounds in a complex mixture (cell-extracted metabolites). I'm unaware of any published methods to do so. So I am thinking of making my own using a ...
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1answer
180 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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