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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132 views

Why is Aniline a poor substrate for Nitration reaction? [duplicate]

I have been asked to find out which one of the following is a poor substrate for Nitration reaction: Upon encountering this question, my first reaction was the option c, as I know that the nitration ...
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45 views

Why does (2-methoxyethyl)benzene undergo nitration at the ortho position (major product)?

This is an option in a question in which we needed to mark all the correct reactions: According to the answer key, this is a correct option. As an alkyl group is directly bounded to the benzene ring, ...
4
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1answer
77 views

Major product of the nitration of benz[cd]indol-2(1H)-one

Decide major product for given reaction of electrophilic aromatic substitution: Is the major product a because of steric hindrance, or is it b because of hydrogen bonding?
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34 views

How is this Cope Reaction forming Ethene as major product?

I have been asked to find the major product of the reaction: As this a case of pyrolysis of $3^{\circ}$ Amine Oxide (or, in other words, Cope Reaction), I figured there are two possible products ...
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22 views

Purify 65% nitric acid to 98% (WFNA)

What is the simplest way to purify 65% nitric acid (HNO3) to white fuming nitric acid (WFNA which is 98% pure)? Is it dehydration with concentrated sulfuric acid (H2SO4)? Is distillation needed to be ...
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1answer
96 views

Relative acidity of acetic acid derivatives with strongly withdrawing substituents

What would be the order of $\mathrm{p}K_\mathrm{a}$ values of the following: $\ce{O2N-CH2-CO2H},$ $\ce{Me3\overset{+}{N}-CH2-CO2H},$ $\ce{NC-CH2-CO2H},$ $\ce{HO-CH2-CO2H}?$ Since only the groups ...
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1answer
54 views

iupac name please? [closed]

I am kind of confuse here whether to number $\ce{NO_2}$ or double bond in the ring.
3
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1answer
68 views

How to carry out cyclization of 1‐(2‐methylbutyl)‐2‐nitrocyclohexane?

How the cyclization can take place as there is no other functional group than $\ce{NO2}?$ One way that I can think of is photochemical bromination which occurs selectively at tertiary center which ...
2
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1answer
52 views

Numbering for the IUPAC name of this benzene derivative [duplicate]

My first guess was 2-chloro-4-nitrotoluene, but this was not among the choices for this question. My teacher says we will begin numbering from Cl, as halogens have higher priority than a nitro-group. ...
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30 views

Reaction mechanism of tin(II) chloride to reduce nitrobenzene to aniline [duplicate]

Does anyone know the reaction mechanism for $\ce{SnCl2}$ to reduce nitrobenzene to aniline? I can only find $\ce{Sn/HCl}$ reaction mechanism but can't seem to find any information on $\ce{SnCl2}.$ ...
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Does the Henry reaction (nitroaldol reaction) work on carboxylic-acid-derived carbonyls?

In reading about the Henry reaction in textbooks and online, I can't find any treatment of the reaction with the carbonyls of esters or acyl halides. I am imagining the reaction would be similar to ...
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27 views

Reaction of Methyl Cyanide with nitroethane

I want to know the products of reaction of Methyl Cyanide with nitroethane in presence of (Sodium ethoxide + ethanol) and then hydrolysed in concentrated Acidic medium. According to me ,reaction ...
3
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1answer
121 views

Nitration vs Nitrolysis

I am interested in nitrating an aromatic ester in a solution of dichloromethane. I found the following paper that describes creating a nitric acid solution in dichloromethane using KNO3 and sulfuric ...
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4answers
483 views

Most favorable position of attack of an electrophile on 4-trifluoromethyl-1,2-diphenylbenzene

Problem This problem is from a FIITJEE AITS paper Which position is most favorable for the attack of an electrophile? Answer My attempt The more favorable position for attack should be the on the ...
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1answer
521 views

Why is phosphorous pentoxide a dehydrating agent?

$$\ce{HNO3 + P2O5 -> 2HPO3 + N2O5}$$ In this reaction, both nitrogen and phosphorus have the same oxidation number before and after the product is formed. Since the $+5$ oxidation of nitrogen is ...
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1answer
118 views

Nitro-substitution [closed]

Here I expected (b) to happen via nucleophilic substitution, but contrary to that (a) is the one occuring. What exactly is happening here?
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1answer
1k views

Why does p-nitrophenol give sodium bicarbonate test, but o-nitrophenol does not?

Both ortho- and para-nitrophenol are less acidic than carbonic acid. But still paranitrophenol reacts with sodium bicarbonate to give carbonic acid and sodium paranitrophenoxide. However, this is not ...
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1answer
33 views

Do alkylhydroxylamines form N-nitrosamines?

Usual secondary amines can form N-nitrosamines with nitrosating agents, e.g., $\ce{KNO2}$, and are therefore forbidden in metalworking fluids. But can alkylhydroxylamines form N-nitrosamines with ...
2
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0answers
58 views

Seeing a case where both + and - mesomeric effect is shown

I came up with that -N=O group shows both +M and -M and I understand that. In my textbook it was written that " -N=O group attached to benzene shows both + m and -m depending on the nature of other ...
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2k views

Reduction of nitrobenzene in alkaline medium

My teacher listed out the following set of reactions under the aforementioned topic: He explained the formation of azoxybenzene as follows. Reduction of nitrobenzene produces 2 intermediates: ...
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2answers
268 views

Nitrocellulose (flash paper) synthesis without Sulfuric Acid?

According to the Wikipedia page on Nitrocellulose: The process uses nitric acid to convert cellulose into cellulose nitrate and water: $$\ce{3HNO3 + C6H10O5 ->[H2SO4] C6H7(NO2)3O5 + 3H2O}$$ ...
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2answers
132 views

How to experimentally determine the elemental composition in fingernails?

I am doing a project in my highschool about analysing C/N and C/S ratio of finger nails of various ages and sexes. Please suggest me a way to do this. I don't know where to start, I know the various ...
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74 views

How far does the delocalisation (resonance) effects for substituents extend for a conjugated system?

Let's say we have a conjugated system like this one: Now, the delocalisation of the benzene electrons with the nitrate system means that the ortho, and para positions on the immediate benzene ring ...
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138 views

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

Most preparations for nitrocellulose from $\ce{(KNO3 + H2SO4)}$ mixture require the use of an ice bath during the process of dissolving $\ce{KNO3}$ into $\ce{H2SO4}$. Last time I did this I omitted ...
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1answer
103 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
71 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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2answers
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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
1k 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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0answers
131 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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42 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
157 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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220 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
31 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, ...
2
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1answer
212 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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2answers
19k views

Nitration of aniline [duplicate]

(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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304 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 ...
2
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1answer
1k views

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

I came across this question. According to me, $\ce{NO}$ should have a shorter bond length as it has a triple bond, while $\ce{NOCl}$ has a double bond. But the answer is given that $\ce{NO}$ has ...
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1answer
2k 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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0answers
88 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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287 views

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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0answers
1k 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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889 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
1k 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
1k 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?
5
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1answer
228 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
236 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
156 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
4k 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 ...
6
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1answer
666 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 ...