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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Why does Bachmann reaction differ in batch characteristics as opposed to flow characteristics

I have studied this reaction for over a year and it makes zero sense. When synthesizing HMX from Bachmann reaction, an important intermediate is DPT. DPT is formed by reaction of nitric and hexamine ...
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2 answers
84 views

Can anisole be nitrated only with nitric acid?

Is it possible to nitrate anisole using only concentrated nitric acid? Or is it necessary to use sulfuric acid or acetic anhydride? Could you please help me with some references?
5 votes
2 answers
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Can primary amine be produced using Grignard reagent?

I found a way to produce Secondary Alkyl Amines using Grignard Reagent. Ref: Z. Huang, J. Lv, Y. Jia, Chemistry Select 2016, 1, 5892. DOI: 10.1002/slct.201601464 But I want to know if I can use $\ce{...
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1 answer
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Why is it wrong to draw the Lewis structure of a molecule's atoms and then figure out the Lewis structure of that molecule

When drawing for example the Lewis structure of nitrate ion (NO3)^-1 whould it be wrong to draw nitrogen and oxygen separately and then try to figure out the structure of the ion? In that case does ...
2 votes
1 answer
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How to synthesize anhydrous zinc(II) nitrate?

I'm interested in making anhydrous zinc nitrate. I know it decomposes fairly rapidly if you heat it. It is also soluble in ethanol. Would another desiccant or a molecular sieve do the trick? Or maybe ...
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Preparation of m-nitroaniline from m-dinitrobenzene [duplicate]

Consulting various Organic Chemistry resources, I have found two reactions for the purpose stated in the subject: First reaction: Second reaction: But, I cannot find the reaction mechanism by which ...
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68 views

Nitrocellulose using Sodium Bisulfate instead of Sulfuric Acid

Recently, I came across this question with regards to making nitrocellulose using only nitric acid and not sulfuric acid: Nitrocellulose (flash paper) synthesis without Sulfuric Acid? One of the ...
0 votes
1 answer
266 views

What are the resulting conjugate acid and base of phenol and 4-nitrophenol

I have to complete the equation 4-nitrophenol + phenol ---> and then label the acid, the base, the conjugate acid and the conjugate base. I think the answer ...
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1 answer
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What role does ammonium play in the explosion of ammonium nitrate? [duplicate]

I read that ammonium is the "fuel" and nitrate is the "oxidizer". The nitrate oxidizes because it's a nitro group, but what's the mechanism of the ammonium?
1 vote
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Selective reduction of aromatic nitro group

In the following compound, is it possible to selectively reduce the aromatic nitro group to an amine, as shown in the reaction? I fear that the methods usually used to reduce aromatic nitro compounds,...
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1 answer
354 views

Nitro as a leaving group in an aromatic ring

I came across a chemistry problem posted on Discord. The objective is to propose a reagent that will enable the following reaction to occur: One proposed answer for the mysterious Reagent D is sodium ...
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Nitration of haloarene

Question: Convert benzene to 4-bromonitrobenzene. My attempt: Answer given: Is my solution correct? Can aryl halodes react directly with $\ce{AgNO2}$ to form aryl nitrate?
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What happens to water and oxygen produced due to dissociation of nitric acid? [closed]

Nitric acid is yellow in colour due to the dissolution of nitrogen dioxide gas. The nitrogen dioxide is obtained due to thermal dissociation of a portion of nitric acid: $$\ce{4HNO3 -> 2H2O + 4NO2 +...
11 votes
1 answer
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Why is the ortho product major in the nitration of anisole with nitric acid and acetic anhydride?

There is this weird information I found in my organic chemistry book ("Essential Organic Chemistry" by Ranjeet Shahi) The question asks us to give reason as to why the following occurs. ...
4 votes
1 answer
183 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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2 votes
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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, ...
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5 votes
1 answer
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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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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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3 votes
1 answer
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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 ...
-4 votes
1 answer
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iupac name please? [closed]

I am kind of confuse here whether to number $\ce{NO_2}$ or double bond in the ring.
3 votes
1 answer
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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 ...
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2 votes
1 answer
107 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. ...
2 votes
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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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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 ...
4 votes
1 answer
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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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11 votes
4 answers
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Most favorable position of attack of an electrophile on 4-trifluoromethyl-1,2-diphenylbenzene

Problem This problem is from a 2016 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 ...
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1 answer
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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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1 answer
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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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2 answers
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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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1 answer
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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 ...
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2 votes
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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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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: ...
1 vote
2 answers
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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: $$\ce{3HNO3 + C6H10O5 ->[H2SO4] C6H7(NO2)3O5 + 3H2O}$$ ...
0 votes
2 answers
149 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 ...
2 votes
0 answers
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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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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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1 answer
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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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1 answer
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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 ...
8 votes
2 answers
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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 ...
5 votes
3 answers
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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 3-nitrobenzonitrile A to 3-aminobenzonitrile B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
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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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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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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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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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1 answer
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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 votes
1 answer
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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 ...
5 votes
2 answers
27k 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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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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2 votes
1 answer
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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 ...