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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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Methylation of nitroalkanes with diazomethane

It is known that diazomethane can methylate various compounds with acidic hydrogens. Diazomethane is most well-known for the efficient synthesis of methyl esters from carboxylic acids. Clayden, ...
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What is the major product of the nitration of N,N-dimethylaniline? [duplicate]

What is the major product when N,N-dimethylaniline, $\ce{C6H5N(CH3)2}$, reacts with concentrated nitric acid (conc. $\ce{HNO3}$) in presence of concentrated sulphuric acid (conc. $\ce{H2SO4}$)? Here, ...
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Effect of H-bonding on o-nitrobenzoic acid

My argument here is regarding the acidity of o-nitrobenzoic acid being greater than p,m-nitrobenzoic acid. In o-nitrobenzoic acid, there is an intramolecular hydrogen bond which makes the bond ...
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Oxidation state of N in NO from resonance

I know from a textbook that nitrogen has an oxidation state of +II in NO, and this is easily verified if O is assigned -II. However, if one looks at the resonance structure and assigns covalent ...
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169 views

Converting phenol to para-nitrophenol via nitrosophenol

Our class 12 text book says that if we treat phenol with mixture of concentrated $\ce HNO_3$ and $\ce H_2SO_4$, instead of nitration, the ring is oxidized to quinone. So, the book proposes that we ...
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1answer
334 views

Are there any reducing agents for reduction of nitrobenzene to aniline other than Sn/HCl?

I was taught that Sn/HCl should be used for reduction of nitrobenzene to aniline. Can I ask if there are any alternative reducing agents (for example, LiAlH4?) to do the same task?
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1answer
211 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?
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106 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 ...
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1answer
76 views

Fast way to isolate 4-nitrophenol from 4-aminophenol

I'm working in the lab with a very old (like 30 years old) sample of 4-nitrophenol, wich of course has been reduced with the time to 4-aminophenol. I need to isolate both reagents and work only with ...
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1answer
87 views

Methylnitrobenzene ring formation Synthetic Route

I know the malonic ester is probably used to make propanoic acid or some carboxylic acid, and then joined to the methylnitrobenzene. But I just can't figure out what glues to the methyl. I know the ...
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1answer
959 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 ...
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1answer
245 views

Nitrosonium ion in the nitration of phenols

Peter Skyes 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 ...
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Color change of nitroglycerin. Potential hazard?

I recently nitrated around (~7mL) of glycerol through a process I have performed many times before. The nitroglycerin has been stored for ~3 weeks, and I noticed a drastic change in color from clear ...
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1answer
923 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. ...
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2answers
509 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 ...
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1answer
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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 ...
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1answer
109 views

How to convert benzene to 2-nitrostyrene as the major product?

How to convert benzene to 2-nitrostyrene as the major product? I actually came up with a conversion but I don't know if it's correct or not:
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1answer
760 views

Why are nitro compounds with at least one alpha-H soluble in NaOH?

Are all the nitro-compounds having at least one alpha-$\ce{H}$ soluble in $\ce{NaOH}$? And what does solubility has to do with alpha-$\ce{H}$? I was reading about tautomerism today and got stuck on ...
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216 views

Is ‘nitro-hydrogen’ a valid structure for HNO2?

The structure of $\ce{HNO2}$ is commonly given as: $$\ce{O=N-OH}$$ This structure has a $\ce{OH}$ group which is bonded to an $\ce{N=O}$ group. I’m wondering whether an alternative structure is ...
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331 views

Why is ethanol used in catalytic reduction of nitro group to an amine? [closed]

$$\ce{R-NO2 +C2H5OH + H2 (g)->[Pt/Pd/Ni] R-NH_2}$$ The above equation represents catalytic reduction of nitro group to amine. What is the role of ethanol in it? I understand that $\ce{Pt/Pd/Ni}$ ...
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81 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 ...
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27 views

Gaseous nitration of glycerin

Could nitric and nitrous oxides react with glycerin to produce nitroglycerin? What conditions would I need in order to make that work?
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2answers
2k views

Can sodium dithionite reduce the nitro group of 2-nitrobenzoic acid?

Can sodium dithionite reduce o-nitrobenzoic acid to anthranilic acid under basic conditions with mild reflux? If so, how could I separate anthranilic acid from the reaction mixture?
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1answer
213 views

Diazonium ion positive charge

I am confused about the nature of the positive charge on the nitrogen atom in the diazonium ion. Where does it come from? That nitrogen atom has 4 bonds, but I cannot deduce whether one of them is ...
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Nitration of (E)-4-Phenyl-3-buten-2-one

What would happen if (E)-4-Phenyl-3-buten-2-one, shown above is nitrated, and is this compound more or less reactive than benzene? My Attempt: By drawing the resonance structures of the above ...
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1answer
485 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 ...
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1answer
719 views

Can the electrophile attack at the position of the NH2 group in nitration of aniline?

In the nitration of aniline, we observe the formation of a meta-substituted product (47%) almost as much as a para (52%). However, can't the electrophile attack at the position where $\ce{-NH2}$ is ...
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292 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 ...
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1answer
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1answer
2k views

Is picric acid a very strong acid?

Picric acid has nitro groups in para and ortho positions, so it has great possibility to go for resonance, thus it is supposed to be a very good acid. But a question arises! The $\ce{O}$ of $\ce{-OH}$...
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1answer
708 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 ...
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1answer
328 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
1k 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. I don't know if it's possible. Please correct me if I'm wrong. Also, what would be the nature of it?
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1answer
397 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
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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
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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
75 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
15k 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
336 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? Thank you in advance
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1answer
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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
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 ...
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0answers
438 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
136 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
4k 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
375 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
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 ...
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1answer
5k 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
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 ...