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Questions tagged [nitro-compounds]

For questions about the synthesis, properties, and reactions of organic compounds containing the -NO2 group i.e. nitro-compounds.

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44
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3answers
10k views

Why does nitration of N,N-dimethylaniline occur at the meta position?

The nitration of N,N-dimethylaniline with $\ce{H2SO4}$ and $\ce{HNO3}$ gives mainly the meta product, even though $\ce{-NMe2}$ is an ortho,para-directing group. Why is this so?
21
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3answers
1k views

What is Y-aromaticity? Is the trinitromethanide anion aromatic?

The wikipedia article on trinitromethane claims that: There is some evidence that the anion (which obeys the $4n+2$ Hückel rule) is aromatic. Unfortunately the citation is behind a paywall so I ...
17
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3answers
8k views

Selective nitro reduction of poly nitro compounds

Is there any way through which I could selectively reduce one $\ce{NO2}$ group from a dinitro- or trinitro- compound to an amine. I was reading Solomons and Frhyle and it says that m-dinitrobenzene ...
15
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4answers
20k views

Acidity order of nitrophenols

As in other posts I have seen and learnt that, if one is given four compounds, namely para-nitrophenol, ortho-nitrophenol, meta-nitrophenol and phenol and is told to arrange them in order of acidity, ...
13
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4answers
6k views

Which chemical properties make a substance explosive?

I know that some chemical substances are used as explosives. Amongst the most famous nitroglycerin in dynamite and cyclonite in C-4. Which chemical properties (I suspect that physical properties have ...
13
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2answers
431 views

Mechanism of initiation in contact explosives?

It's well known that undiluted nitroglycerin will explode when subjected to a physical shock. What is happening as a result of the physical shock that sets off the explosive reaction? In particular, ...
12
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3answers
6k views

How can we synthesize para-nitrophenol

During nitration of phenol, both para- and ortho-nitrophenols will be formed. Is there any way in which we can synthesize para-nitrophenol only?
12
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2answers
59k views

Nitrobenzene reduction with (tin) Sn catalyst: Why is C-H bond cleavage preferred over O-H bond cleavage?

I am trying to understand this mechanism for nitrobenzene reduction with $\ce{Sn/HCl}$. I do not understand why it implies that you pull off the $\ce{C-H}$ hydrogen instead of the $\ce{O-H}$ hydrogen ...
11
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3answers
2k views

Reduction of α,β-unsaturated nitro compounds

Would it be possible to reduce a α,β-unsaturated nitro compound to a saturated amine using for example $\ce{NaBH4}$? I know these kind of compounds will be reduced by hydrogenation using a $\ce{Pt/C}$ ...
10
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1answer
621 views

What is the significance of the 2 and 4 positions in 2,4-DNP?

2,4-dinitrophenylhydrazine, a popular laboratory reagent is used to identify carbonyl compounds by forming 2,4-dinitrophenylhydrazones, which are often red or yellow colored precipitates. Why is the ...
10
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1answer
5k views

Why is picric acid more acidic than carbonic acid?

I just had a question in a test asking to compare the relative acidity of picric acid (TNP) and carbonic acid, $\ce{H2CO3}$ (not phenol). It turns out that TNP is more acidic. I have no idea why? Is ...
9
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1answer
21k views

Reaction mechanism for reduction of nitrobenzene to aniline in catalytic and acidic media

Can anyone explain the reaction mechanism of the two reactions given below? They are the conversion of nitrobenzene to aniline in catalytic ($\ce{H2/Pd}$ in ethanol) and acidic ($\ce{Sn/HCl}$ or $\ce{...
9
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1answer
3k views

What will be the major product on chlorination of m-nitrophenol?

I came across a question asking for the major product on chlorination of m-nitrophenol. In my opinion the deactivating nature of nitro group should control the regioselectivity, but I found out the ...
9
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1answer
228 views

Aromatic ring substitution: how are MNT and DNT further nitrated if nitro groups deactivate benzene rings?

This is probably a common question because it involves TNT precursors, but if an $\ce{NO2}$ group deactivates benzene rings toward electrophilic aromatic substitution reactions, then how can toluene ...
8
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2answers
2k views

How can an aromatic ketone be reduced in the presence of a nitro group?

Is it possible to reduce an acyl group to an alkane, but still keep a nitro group intact without its reduction to an amino group? A Clemmensen reduction would reduce the nitro group, and it seems like ...
8
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1answer
502 views

Why are triamino compounds so rare?

I was doing a reaxys substructure search for the compound shown on the left below, with the 3 amines on 1 carbon. However, the closest I found were all trinitro compounds like on the right. I would ...
8
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2answers
311 views

What products do 4-nitrobenzaldehyde and 3-nitrobenzaldehyde give in a crossed Cannizzaro reaction and why?

What are the products of reaction of 4-nitrobenzaldehyde with 3-nitrobenzaldehyde in the presence of $\ce{NaOH}$ when they show Cannizzaro reaction? To my understanding, 4-nitrobenzaldehyde has more ...
8
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1answer
2k views

Reaction between phenol and nitrous acid

My question is about the products formed when phenol reacts with nitrous acid. I googled it and reached this PubChem paper (DOI: 10.1016/S0045-6535(02)00857-3), which states: It was found that ...
7
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3answers
5k views

Is the aromaticity broken in some resonance structures of para-nitro-aminobenzene?

According to my course of organic chemistry, para-nitro-aminobenzene has to break his aromaticity to delocalize the electrons of the amino-group in the nitro-group. I don't really see this, when I ...
7
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2answers
5k views

Why do nitro groups confer explosive tendencies?

When suggesting nitration of an aromatic compound in the synthesis of some organic molecule, it was raised that this route should be avoided as to prevent things from going "ka boom." An explanation ...
7
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1answer
2k views

Synthesis of 2-methyl-4-nitrophenol from benzene?

Benzene first reacts with the reagents $\ce{CH3Cl/AlCl3}$, to attach a methyl ($\ce{CH3}$) group to the benzene ring. Then I suggested reacting with $\ce{OH-}$. Because the methyl group is an ...
7
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1answer
5k views

Nitration of pyrrole with sulfuric and nitric acids

Would 2,5-dinitropyrrole be a product of nitration of pyrrole with $\ce{H2SO4/HNO3}$? It seems that 2,5-dinitropyrrole is not formed when using $\ce{Ac2O/HNO3}$ (ref 1). Is this just because of the ...
7
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1answer
2k views

Why does a mixture of nitrous acid with concentrated nitric acid cause nitration of benzene instead of nitrosation?

A question came up in our worksheet to predict the reaction product of nitrous acid and concentrated nitric acid with benzene. I quickly recognized it to be similar to the nitration reaction. ...
6
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1answer
6k views

Why is picric acid more explosive than TNT?

I've recently read that trinitrophenol (picric acid - relative effectiveness factor $1.20$) is more explosive than trinitrotoluene (TNT - relative effectiveness factor $1.00$). Personally, I think ...
6
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2answers
3k views

Role of Alcohols(EtOH,MeOH) in nitro reduction used for Metal(Sn,Fe)

I'm trying to reduce an aryl nitro group. I understand that these reactions are radical reactions by the metal, but I don't understand why alcohols are used as the solvent. Are they used as a source ...
6
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1answer
702 views

Amine addition to nitro group

What is the mechanisms of this reaction? How feasible is this reaction? Can it happen under relatively mild conditions if it is intermolecular?
6
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1answer
2k views

Is 4-nitrobenzaldehyde or 4-aminobenzaldehyde more likely to be hydrated?

Of 4-nitrobenzaldehyde and 4-aminobenzaldehyde, which has the higher $\ce{K_{eq}}$ of hydration? $\qquad \qquad$ Steric factors can likely be ignored in this problem since we are dealing with ...
6
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1answer
2k views

Are groups other than carbonyl reduced by Clemmensen reduction?

According to my textbook, Clemmensen reduction reduces only aldehydes and ketones to alkanes. But in this question: $\ce{Zn-Hg/HCl}$ has reduced both the ketonic and nitro group. Correct answer given ...
6
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2answers
91 views

How to weight picric acid?

Picric acid is stored under a layer of water to prevent an explosion. What is the right way to measure the amount of picric acid that taken out? It is wet and containing water.
6
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1answer
506 views

Nitrosonium ion in the nitration of phenols

Peter Sykes mentions in the book Guidebook to Mechanism in Organic Chemistry (6th ed.) on p. 137 that: Highly reactive aromatic compounds, such as phenol, are found to undergo ready nitration even ...
5
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1answer
462 views

Is Nitroglycerine a Nitro Compound or an Ester?

I looked up nitroglycerine in a science dictionary (Oxford Dictionary of Science, 2003), and it explicitly mentions that nitroglycerine is an ester and not a nitro compound. However my teacher told ...
5
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1answer
178 views

Major product in nitration

My approach was that when the carbon attached was a secondary one, it would have a greater inductive effect compared to the primary one. Why is the answer 3? Is it due to steric reasons or am I ...
5
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1answer
5k views

Chemoselectivity in reduction of 3′-nitroacetophenone

When 3′-nitroacetophenone is treated with sodium borohydride, only the carbonyl group is reduced (top); however, when reacted with tin and hydrochloric acid only the nitro group is reduced (bottom). ...
5
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0answers
171 views

Reaction of alkenes (localised π bond) with nitrating mixture

The nitrating mixture for the nitration of benzene contains many strong electrophiles (e.g $\ce{H2SO4}$, $\ce{NO2+}$). All of these could, presumably, add across the π bond in a molecule containing a ...
4
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2answers
307 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{...
4
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2answers
897 views

What is the function of nitrobenzene as a solvent in Friedel Crafts alkylation reaction?

I would like to know what is the function of nitrobenzene as a solvent in Friedel Crafts alkylation reaction. Answer to this question suggests that Friedel Crafts reaction is not possible with ...
4
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3answers
4k 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 ...
4
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2answers
428 views

Cannizzaro reaction versus Nitroaldol reaction

In Clayden et al. on p. 696 the following nitroaldol reaction is listed: Later in the same chapter they explain the Cannizzaro reaction. Why is the yield of this nitroaldol reaction particularly ...
4
votes
1answer
22k views

Reaction of an alkyl halide with silver nitrite

I want to know that whether both alkyl nitrite and nito alkane are produced or if nitroalkane is the only product. There are many different (contradicting) things written in different books that is ...
4
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0answers
141 views

Can a nitro compound be reduced to an amine by electrolysis?

Several methods are known for the reduction of a nitro compound to an amine, including catalyctic hydrogenation. I am wondering if this can be done by electrolysis. If we take the simplest ...
3
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2answers
7k views

Structure of N2O2

I've drawn a structure of $\ce{N2O2}$ like this: $$\ce{:\overset{\large.\!\!.}{\underset{\large.\!\!.}{O}}-N#N-\overset{\large.\!\!.}{\underset{\large.\!\!.}{O}}:}$$ I don't know if it's possible. ...
3
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2answers
4k views

How to selectively convert benzene to p-nitrotoluene?

I converted benzene into toluene by Friedel-Crafts alkylation reaction. Then by nitration I got two compounds o-nitrotoluene and p-nitrotoluene. Is it possible to get only p-nitrotoluene?
3
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1answer
158 views

Nitration of aromatic compound with alkyl substituents

For 1,1,4,4-tetramethyl-1,2,3,4-tetrahydronaphthalene: What would be the products following a standard nitration with $\ce{NO2+}$? My reasoning is thus: Since the substituent group is alkyl then it ...
3
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1answer
99 views

Are highly nitrated cyclopentadiene compounds possible?

Has anybody synthesized di- or higher nitrated cyclopentadienes possibly with methyl or other groups in the 1 position (analogs of TNT)?
3
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0answers
424 views

Selectivity of Zinin Reduction

What is it, that makes the Zinin Reduction a selective reduction, and not a complete reduction, in the case of dinitrobenzenes? Also, is the reaction a selective one even when it is done for aliphatic ...
2
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1answer
632 views

Compatibility of Grignard reagents with aromatic nitro groups [closed]

Is it possible to form a Grignard reagent from 1-chloro-3-nitrobenzene, as shown below? Specifically, will the nitro group react with the Grignard reagent formed?
2
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2answers
3k views

How to transform an aliphatic primary amine to the corresponding nitro compound?

Could you suggest a reagent or procedure to transform an aliphatic primary amine to the corresponding nitro compound. I know this is a bit backwards of a request because the usual procedure is the ...
2
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1answer
99 views

Which set of reactants is better for preparation of 1-methoxy-4-nitrobenzene?

I've got two set of reactants: 4-nitrobromobenzene + sodium methoxide sodium 4-nitrophenoxide + bromomethane I've got to tell which reaction is more preferable among these two. The first reaction ...
2
votes
1answer
309 views

Which has greater N-O bond length: NO or NOCl?

I came across this question. According to me NO should have a shorter bond length as it has a triple bond, while NOCl has a double bond. But the answer is given that NO has greater bond length than ...
2
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0answers
20 views

A question about nicotinamide adenine dinucleotide

In the structure of NAD+, why does the nitrogen of pyridine bind covalently to the the first carbon of glucose while the anion stabilizing the nicotine amide ion is the phosphate group? In other words,...