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49 votes
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Why does lemon juice reduce the "fish" odor of sea food — specifically fish?

There are two cases, both related to acid-base reactions. Both are also partial reasons why so many fish recipes use lemon juice. Fish, especially sea fish, naturally contain trimethylamine-N-oxide $\...
Poutnik's user avatar
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21 votes
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Selective nitro reduction of poly nitro compounds

Is there any way to predict which nitro group will be reduced After having gone through three pages of Google Scholar and reading several research papers looking for an answer, there is definitely no ...
Gaurang Tandon's user avatar
21 votes

What is this fluorinated organic substance?

The name of the compound is 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (CAS #: 140681-55-6), which is commonly known as Selectfluor, a trademark of Air Products ...
Mathew Mahindaratne's user avatar
19 votes

Does aniline react with diazonium ions at C or N?

In general, for anilines reaction at nitrogen is kinetically faster than reaction at carbon. However, the C-substituted product is usually more stable than the N-substituted product, so can prevail ...
orthocresol's user avatar
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18 votes

Usage of ammine vs amine in nomenclature

(Will do more research into ammines come February.) Premise Ammonia is spelled with two 'm's. The more natural derivative of the word in a linguistic sense would also have the same number 'm's. Thus ...
Linear Christmas's user avatar
18 votes
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Does aniline react with diazonium ions at C or N?

This is a really interesting question and the answer is that the reaction of benzenediazonium chloride with aniline is a bit different to most of the reactions of benzenediazonium salts in that the ...
Waylander's user avatar
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14 votes
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What is this fluorinated organic substance?

That is generally known as Selectfluor, a source of electrophilic fluorine. The zig-zag line is a 2-D representation of the third ethylene $\ce{-CH2-CH_{2} -}$ unit that links the two nitrogens. more ...
Waylander's user avatar
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12 votes
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Can a cyclic amine form an amide?

The heterocycle in this question is indole and is aromatic. This means that the N lone pair is delocalised and not readily available for nucleophilic attack. Think of it as similar in reactivity to a ...
Waylander's user avatar
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11 votes
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Identify two amines

The proposed strucutre of these compound are, correct me if i am wrong.
Khan's user avatar
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11 votes

Byproducts of LiAlH4 reduction of amides

Organic chemistry textbooks I flipped through usually don't focus on by-products, only noting that LAH ($\ce{LiAlH4}$) in dry solvent (THF, diethylether) is necessary for reduction, but when one ...
andselisk's user avatar
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11 votes
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Is steric inhibition of resonance or steric inhibition of protonation dominant in o-toluidine?

The reason for the decreased basicity is essentially the ortho-effect as outlined here: Ortho-effect in substituted aromatic acids and bases. Your question on the other hand asks about a seeming ...
Martin - マーチン's user avatar
11 votes
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Hoffman broamide degradation but with alkoxide as base instead of NaOH

This answer is wrong, the answer should be the carbamate 4. The reaction intermediate is the isocyanate which is captured by MeOH to give the carbamate (std Hofmann mechanism below from ...
Waylander's user avatar
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10 votes

Identify two amines

$\ce{Fc}$ stands for ferrocenyl. So the first compound is an amide of ferrocenecarboxylic acid and tetramethylene diamine, and the second compound is p-ferrocenyl aniline.
aventurin's user avatar
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10 votes
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What is the pKa of methylamine

Both sources are correct. However, they are referring to two different $\mathrm{p}K_\mathrm{a}$ values. $$\ce{H3C-NH3+ <=>[$K_\mathrm{a1}$] H3C-NH2 + H+ <=>[$K_\mathrm{a2}$] H3C-NH- + 2 H+...
Jan's user avatar
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10 votes
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Formamide and Hoffmann Bromamide Reaction

I have spent a lot of hours to find the evidence to support OP's idea of formamide may undergoes Hoffmann degradation reaction, but I can't find any. However, I find at least one publication, which ...
Mathew Mahindaratne's user avatar
10 votes
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Do amines or alcohols have stronger intermolecular hydrogen bonds?

The boiling point of non-ionic compounds are highly depend on their H-bonding abilities. For example, boiling point of water (molar mass: $\pu{18.02 g/mol}$) is $\pu{100 ^\circ C}$ at $\pu{1 atm}$ ...
Mathew Mahindaratne's user avatar
10 votes

Do amines or alcohols have stronger intermolecular hydrogen bonds?

Mathew Mahindaratne has provided analysis based on experimental values of the boiling points of the two compounds. I would like to offer a different view using bonding analysis. Before I begin ...
Tan Yong Boon's user avatar
10 votes
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Ritalin/Concerta/Methylphenidate is an amphetamine?

Firstly, I'll mention that I'm not an expert on psychoactive drugs and their classifications; this is just based on my understanding of the situation as a chemist. As far as chemical structures go, ...
orthocresol's user avatar
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9 votes

What are the products of the reaction between methanamine and nitrous acid?

No chance to get alkenes from methanamine because there's no $\beta$-hydrogen for E2 elimination. And E1 elimination isn't going to work because you're not going to generate a methyl cation from the ...
Zhe's user avatar
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9 votes

Selectivity of diazo-coupling with p-amino phenol

I think the right way to approach this question isn't "we don't know the product, let's try to reason it out from first principles"; rather it should be more like "we found that this is the product ...
orthocresol's user avatar
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9 votes
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Regioselectivity in coupling reactions of α-naphthol

The product at the para-position is more stable as it allows the compound to exist in the quinoid form, rather than only in the benzoid form: This is important as in your case, if the substituent $\...
Aniruddha Deb's user avatar
9 votes
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Why is para-aminobenzoic acid more acidic than ortho-aminobenzoic acid?

The problem in ortho-aminobenzoic acid is that the acidic hydrogen of carboxylic group is H-bonded with the lone pair of nitrogen in amino group. As a result it is more difficult to extract it ...
napstablook's user avatar
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9 votes
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Comparing the basicity of heterocyclic amines

The correct order is in fact $(\bf{d}) \gt (\bf{b}) \gt (\bf{c}) \gt (\bf{a})$, the reason for this is as follows. $(\bf{a})$ is definitely last in this order of basicity since its lone pair is ...
Safdar Faisal's user avatar
9 votes
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Formation of Aniline from Chlorobenzene

Your textbook's text is correct but the reaction image is incomplete. Reaction of chlorobenzene with ammonia in presence of both the cuprous chloride and cuprous oxide forms aniline but via two ...
Nisarg Bhavsar's user avatar
8 votes

Selective nitro reduction of poly nitro compounds

Zinin reduction was discovered by a Russian organic chemist Nikolay Zinin in 1842 (Wikipedia) and revieved by Porter (1973; Ref.1). As pointed out by @Gaurang Tandon and @Nilay Ghosh in their answers, ...
Mathew Mahindaratne's user avatar
8 votes

Selective nitro reduction of poly nitro compounds

Source: Maity, Sunil K.; Pradhan, Narayan C.; Patwardhan, Anand V. "Reduction of p-nitrotoluene by aqueous ammonium sulfide: Anion exchange resin as a triphasic catalyst". Chemical Engineering Journal....
Nilay Ghosh's user avatar
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8 votes
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Why amine salts are soluble in water?

Amine salts are: charged polar hydrogen-bonding (unless they're quaternary) There some cross-over between those categories, but all will increase solubility in water, a polar solvent, and decrease ...
NMJD's user avatar
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8 votes

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

My answer is intended to support Waylander's suggestion elsewhere. I thought it'd be better to give OP some insight of this reduction mentioned (Ref.1). To my knowledge, after doing thorough ...
Mathew Mahindaratne's user avatar
8 votes
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Why doesn't hydrolysis of isocyanides take place in basic medium?

The main reason for the inability of alkyl isocyanides to undergo hydrolysis in basic medium is because the negative charge at the carbon atom $(\ce{R-\overset{+}{N}#\overset{-}{C}\!:})$ repels the ...
Nilay Ghosh's user avatar
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