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0 votes
0 answers
60 views

Conflict: Sandmeyer reaction and Gattermann reaction

So it is known that benzene diazonium chloride when reaction with cuprous(I) chloride would produce a chlorobenzene which is called Sandmeyer reaction. Now for the same salt, if we react it with ...
Xlomer's user avatar
  • 11
4 votes
1 answer
307 views

Nomenclature of C6H5CO-O-NH2

How to name the following compound using IUPAC nomenclature? I found benzyl carbamate to be very close to my structure, but couldn't find an exact compound online which matches mine.
kzmom's user avatar
  • 51
0 votes
0 answers
37 views

comparing basic strength of toluidine isomers [duplicate]

I would like to compare the basicity of ortho and para isomers of toluidine.After comparing the pKb values online the order of basic strength is: p—toluidine> m—toluidine> aniline> o—...
TeslaBolt's user avatar
  • 156
0 votes
0 answers
588 views

Mechanism for the synthesis of benzimidazole

I have thought up a mechanism for the synthesis of benzimidazole from o-phenylenediamine and formic acid. I would like to know if it's correct. I have attached it below. My rationale for the ...
user avatar
2 votes
1 answer
1k 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....
user avatar
6 votes
1 answer
650 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 ...
Natru's user avatar
  • 245
8 votes
1 answer
839 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 ...
V.G's user avatar
  • 1,261
7 votes
1 answer
3k 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, ...
WHOOP's user avatar
  • 97
3 votes
1 answer
195 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 ...
Aksh Sarma's user avatar
1 vote
0 answers
27 views

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 ...
wes3449's user avatar
  • 814
3 votes
1 answer
322 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 +...
Zenix's user avatar
  • 1,350
1 vote
0 answers
337 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 ...
Yahel Abraham's user avatar
3 votes
0 answers
1k 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, ...
Techie5879's user avatar
6 votes
1 answer
2k 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?
R Dev's user avatar
  • 313
0 votes
0 answers
914 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 ...
WTS's user avatar
  • 11

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