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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32 views

What's the purpose of an ice bath when preparing a nitration mix from KNO3

Most preparations for nitrocellulose from KNO3+H2SO4 mixture require the use of an ice bath during the process of dissolving KNO3 into H2SO4. Last time I did this I omitted this step and the ...
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1answer
46 views

A question about thiamine [closed]

How does the the nitrogen of thiazole in thiamine acquire a positive charge without being stabilized by another negative charge or by being a salt of an anion?
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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,...
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1answer
65 views

How to get the strongest reaction out of 1kg of guncotton in a space of 15*15*15 meters without using an additional gas source

It would be burnt outside at about 2 degrees Celsius with about 75 percent air humidity, 1400 meters above sea level. Even though that's not exactly true, I'll treat it like pure guncotton. I'm asking ...
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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 ...
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2answers
299 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{...
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17 views

Acidic strength of phenol derivatives

While comparing the strengths of o-nitrophenol and p-nitrophenol, p-nitrophenol is found to be more acidic. The reason I studied for this is $\ce{H}$-bonding in o-nitrophenol which makes the acid more ...
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39 views

The structure of exploding buckminsterfullerene-nitrous oxide compounds

Recently, looking into structures of buckminsterfullerenes, I have found several articles claiming that attaching 12, or “several” nitrous oxide molecules to the buckminsterfullerene will cause it to ...
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2answers
89 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.
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37 views

Favoured position in nitration of pyrrole [duplicate]

I try to figure out the preferred position of nitration (determine whether compound A or B is the major product) by looking at the resonance structures of the intermediate cation. The solution then ...
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1answer
29 views

Any method for testing Nitrate and Nitrite in biological fluids like aqueous humour?

If anyone knows the methods of detection of nitrate and nitrite in biological fluids such as aqueous humor, saliva of animals, please let me know. Any relevant literature for the same is available, ...
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1answer
72 views

Is it possible to create weaker version of guncotton by replacing cotton wool with wood chips or linen cloth?

If the cotton wool was replaced by wood chips or linen (flax) cloth, would the mixture of nitric and sulfuric acids still react with the cellulose in it to produce nitrocellulose? If it would, would ...
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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 ...
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86 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 ...
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1answer
305 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 ...
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491 views

Preference for tin or iron in the reduction of nitrobenzene

My NCERT book(Class 12) said the following for reduction of nitrobenzene using $\ce{Sn/HCl}$ and $\ce{Fe/HCl}$ : Now, I have been following this mechanism for this particular reduction, and it seems ...
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66 views

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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684 views

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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615 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
921 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
626 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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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 ...
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2answers
184 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
121 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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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
504 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 ...
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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
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. ...
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2answers
894 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
97 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 ...
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250 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
1k 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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654 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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139 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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30 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
3k 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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450 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
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 ...
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777 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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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 ...
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1answer
3k views

Which occurs first: nitration or oxidation of aniline by concentrated nitric acid?

Which of the cases is possible or both or none?
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3k 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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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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461 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
482 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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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, ...