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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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11 votes
2 answers
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Is nitroglycerin synthesis within human digestive system from eating soap possible?

Could you make nitroglycerin by eating large quantities of pure glycerine soap? A quick google search told me flatus are 59% nitrogen, but I couldn't find anyone else with my exact question (which ...
Ivory427e's user avatar
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0 votes
0 answers
77 views

Why is picric acid not more steam volatile than p-nitrophenol, if intramolecular bonding results in increased steam volatility?

I understand that relative to p-nitrophenol, o-nitrophenol would be more steam volatile (as p-nitrophenol can form intermolecular hydrogen bonds), but my question lies in the fact that its volatile ...
rania h's user avatar
5 votes
0 answers
130 views

Electrolytic reduction of nitrobenzene in differing media

In my lecture notes it is given that in a weakly acidic medium, nitrobenzene on electrolytic reduction gives aniline, which makes sense to me because there is ample H+ in the medium to continue adding ...
Gaurav Sai Maddipati's user avatar
1 vote
0 answers
71 views

How does Tollen’s reagent reacts with hydroxylamine?

How does the Tollens' reagent react with hydroxyl amines? For example, let's consider phenylhydroxylamine $\ce{Ph-NH-OH}$ reaction with Tollens' reagent. First it yields $\ce{Ph-N=O}$ and on further ...
Aditya's user avatar
  • 35
2 votes
1 answer
155 views

Why can't picric acid be made more acidic by adding nitro groups at the meta positions?

I understand that picric acid is acidic because of the $\ce{-NO2}$ electron withdrawing group, but why can't we add more of those on the meta positions to make it more acidic? Is it because that $\ce{-...
User10001010001000's user avatar
0 votes
0 answers
49 views

Advise on performance vs cost of the Berkland-Eyde Process for direct synthesis of Nitric Acid from atrmospheric air

I am new to chemistry, having gone down an electronics route in my career, so I decided to pick up where my 'O' levels ended (many years ago) and make a better understanding of the topic a sort of ...
Jay M's user avatar
  • 101
-2 votes
3 answers
352 views

Structure of AgNO2 and AgONO [closed]

We had a discussion in class today about the substitution reaction of RX with AgNO2 and KNO2. Pretty unimportant, since those seem just fine. But there were 2 arguments. The root problem was, that we ...
Maddy's user avatar
  • 41
1 vote
2 answers
168 views

"Cleaning" of HNO3 solution using distillation

In many industries, pickling baths are common. These are 10 cubic meter baths containing acid baths that metal components are dipped into prior to surface treatment. When the metals are dipped, some ...
Evaporation123's user avatar
2 votes
2 answers
462 views

What compound was drawn on this sidewalk?

A friend found this in the sidewalk of Kent town of Canterbury: What compound is this, and why would its picture be there?
Aleister Tanek Javas Mraz's user avatar
2 votes
2 answers
136 views

Why did industry develop mainly to fix nitrogen in ammonia (Haber-Bosch) instead of in nitrate?

Since approximately WWI, humanity has been able to fix nitrogen gas from the atmosphere ($\ce{N2}$) into compounds that are much more bio-available, like ammonia and nitrate. The first (hard) step is ...
5th decile's user avatar
3 votes
0 answers
80 views

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 ...
Pulkit Sharma's user avatar
0 votes
2 answers
295 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?
G. Arias's user avatar
5 votes
2 answers
1k views

Can primary amine be produced using Grignard reagent?

I found a way to produce Secondary Alkyl Amines using Grignard Reagent. (source: wiley.com) Ref: Z. Huang, J. Lv, Y. Jia, Chemistry Select 2016, 1, 5892. DOI: 10.1002/slct.201601464 But I want to ...
K M F Ruhan's user avatar
0 votes
1 answer
402 views

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 ...
CaptainAmerica Whyso's user avatar
2 votes
1 answer
249 views

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 ...
Mike's user avatar
  • 21
0 votes
0 answers
39 views

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 ...
Carlos's user avatar
  • 607
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0 answers
706 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 ...
Gallus's user avatar
  • 1
-1 votes
1 answer
65 views

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?
Bob Stephens's user avatar
1 vote
0 answers
366 views

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,...
FusRoDah's user avatar
  • 772
5 votes
1 answer
1k 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 ...
user73910's user avatar
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0 votes
0 answers
79 views

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?
Nilabja's user avatar
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2 votes
0 answers
78 views

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 +...
Raghav 's user avatar
12 votes
1 answer
1k views

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. ...
Dusty_Wanderer's user avatar
4 votes
1 answer
315 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 ...
Aniruddha's user avatar
  • 462
2 votes
0 answers
172 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, ...
Pal's user avatar
  • 549
5 votes
1 answer
109 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?
Jay's user avatar
  • 804
2 votes
0 answers
71 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 ...
Aniruddha's user avatar
  • 462
3 votes
1 answer
177 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 ...
Prajwal Tiwari's user avatar
-4 votes
1 answer
82 views

iupac name please? [closed]

I am kind of confuse here whether to number $\ce{NO_2}$ or double bond in the ring.
Abhinav Sharma's user avatar
3 votes
1 answer
96 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 ...
user avatar
2 votes
1 answer
809 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. ...
Akshat Vats's user avatar
0 votes
0 answers
153 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 ...
Ashu tosh's user avatar
4 votes
1 answer
274 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 ...
user137's user avatar
  • 2,228
13 votes
4 answers
1k views

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 ...
Khushi Ladha's user avatar
2 votes
1 answer
2k 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 ...
R. Anusha's user avatar
  • 181
1 vote
1 answer
139 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?
shreya's user avatar
  • 517
3 votes
2 answers
8k 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 ...
Parteek's user avatar
  • 41
1 vote
1 answer
46 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 ...
IV_'s user avatar
  • 271
2 votes
0 answers
108 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 ...
SM Sheikh's user avatar
  • 111
1 vote
0 answers
6k 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: ...
aren't eistert's user avatar
2 votes
2 answers
2k 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: $$\ce{3HNO3 + C6H10O5 ->[H2SO4] C6H7(NO2)3O5 + 3H2O}$$ ...
mpprogram6771's user avatar
0 votes
2 answers
173 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 ...
pjmathematician's user avatar
2 votes
0 answers
136 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 ...
S R Maiti's user avatar
  • 5,685
0 votes
0 answers
424 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 ...
Francis L.'s user avatar
  • 1,480
-1 votes
1 answer
268 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?
mohamed's user avatar
  • 565
2 votes
0 answers
28 views

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,...
mohamed's user avatar
  • 565
-2 votes
1 answer
78 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 ...
justthisonequestion's user avatar
9 votes
2 answers
3k 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 ...
Mr.HiggsBoson's user avatar
5 votes
3 answers
4k 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 3-nitrobenzonitrile A to 3-aminobenzonitrile B. I would normally reduce a nitro to an amine using $\ce{Pd/C}$ and $\ce{...
Philip's user avatar
  • 51
5 votes
1 answer
452 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 ...
Rajat Sansaniwal's user avatar