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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506 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 ...
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1answer
2k views

Ammonia (NH3) and nitric acid (HNO3)

I understand that by adding Nitrogen to my water my Lucerne plants will grow better. Firtsly, is this correct? Secondly, if so, I further understand that I must add/mix Ammonia (NH3) and nitric acid (...
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2answers
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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. ...
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1answer
501 views

Would Schweizer's reagent dissolve nitrocellulose?

Schweizer's reagent, or tetraamminediaquacopper dihydroxide, is used in the production of rayon. It does this by dissolving the cellulose which can be acidified to form strands of cellulose. I have ...
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4answers
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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, ...
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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 ...
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0answers
172 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 ...
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1answer
137 views

Calculate Solubility [closed]

So I've been looking at some chemistry processes and I was trying to conclude how they got the numbers they got. How would I go about calculating the solubility of Phenyl-2-nitropropene in Isopropyl ...
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1answer
25k 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 ...
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1answer
557 views

Reaction of nitro compounds with strong alkali?

Why does a primary and a secondary nitro compound behave as an acid in the presence of strong alkali whereas tertiary nitro compounds do not? Can anyone explain it with reactions?
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1answer
6k 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). ...
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1answer
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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 ...
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0answers
594 views

Effect of nitrobenzene on solution UV/Vis spectra

I am wondering if there is a difference in the maximum absorbed wavelength of light if nitrobenzene is added to an acidic or basic solution. I've figured that resonance plays a part in some ...
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1answer
168 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 ...
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3answers
9k 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 ...
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2answers
437 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, ...
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3answers
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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 ...
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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 ...
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1answer
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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 ...
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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 ...
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1answer
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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 ...
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1answer
732 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?
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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 ...
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1answer
235 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 ...
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1answer
507 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 ...
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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?
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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 ...
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3answers
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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 ...
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441 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 ...
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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 $\ce{Pt/C}$ ...
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1answer
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Why is nitration of veratrole specific in these positions?

Why do we not need $\ce{H2SO4}$ as an acid catalyst for the di-nitration of veratrole? Why does the 2nd nitro group go to positions 4 or 5, following the directing effects of the methoxy-group? Doesn'...
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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 ...
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1answer
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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 ...
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2answers
61k 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 ...
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1answer
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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{...
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1answer
105 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)?
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4answers
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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 ...
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3answers
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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?
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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?

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