Questions tagged [nitriles]
For questions about nitriles and isonitriles and their organic derivatives such as organic cyanates. Not to be used for inorganic cyanides or related structures; for those, one of the tags ionic-compounds or coordination-compounds will be appropriate.
29
questions
1
vote
0
answers
33
views
Amidine synthesis from nitrile and dimethylamine using n-Buli as a base
I am making LiNMe2 using n-Buli (5.5 equiv.) and dimethylamine (5.0 equiv), -15 ºC, dry THF and under nitrogen atmosphere.
I have been doing the reaction and I can observe conversion of starting ...
- 11
-4
votes
1
answer
73
views
Acidity of Benzenepropanenitrile [closed]
Which is the more acidic hydrogen in the parent chain of this compound?
I am confused while considering the various electronic effects.
- 1
0
votes
0
answers
200
views
Why are nitriles less basic than amides?
Like nitriles have a localised lone pair which amides do not have, as their lone pair is delocalised and still amides are more basic. Why?
I could not find any satisfactory explanation so please ...
1
vote
1
answer
162
views
Why is S-alanine acetylated in the synthesis of S-cathinone?
I came across a method of synthesizing enantiomerically pure S-cathinone using S-alanine which is chlorinated to the corresponding acid chloride which is used in a Friedel-Crafts acylation of benzene. ...
- 49
0
votes
1
answer
631
views
Reaction of Grignard reagent with hydrogen cyanide
Grignard acts as a base with compounds containing acidic hydrogen:
$$\ce{RMgX + R'-OH -> R-H + R'-O-Mg-X}$$
and it acts as a nucleophile with others with an electrophilic site:
$$\ce{RMgX + R'-CHO -...
- 387
2
votes
0
answers
41
views
Chemical analysis of campholene nitrile
I have a problem. I am synthesizing an organic compound called campholene nitrile (2,2,3-trimethylcyclopent-3-en-1-ylacetonitrile).
I need to analyze it. But there's a problem. I do not work for a ...
user102173
1
vote
1
answer
860
views
Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?
The major product obtained in the following reaction is:
Question source: JEE Main 2019
The molecule shown as product is the official answer given by JEE from the given options.
I have written the ...
- 804
3
votes
0
answers
405
views
How many equivalents of Grignard reagent does a nitrile group consume?
I was looking at reactions of grignard reagent with certain kinds of compounds and came across it's reaction with nitrile group:
What I was wondering is what if we don't react the Imine formed after (...
- 1,208
1
vote
1
answer
272
views
Cyanide hydrolysis; could it yield an oxime?
The mechanisms for both acid and base catalyzed hydrolysis of nitriles are clear;
(With the subsequent deprotonation from the hydroxyl) and
(Source)
In both cases, the hydroxyl adds to the carbon ...
- 1,136
0
votes
1
answer
76
views
Naming a nitrile in the middle of an aliphatic chain
What class of compounds does this belong to, if it exists; $$\ce{CH3-CH2-C\equiv N^{+}- CH3}$$
I honestly don't know if it exists; it popped up in my head while I was reading up on nitrile compounds, ...
- 1,136
3
votes
0
answers
70
views
Safety concerns (Cyanide): Dicyandiamide + Polyamine condensation reaction
I am attempting to synthesize a poly-amine polymer by condensation between dicyandiamide (also known as cyanoguanidine and dicyandiamine) and diethyltriamine. The polymer is a kind of dye fixative ...
- 586
5
votes
1
answer
721
views
On the stabler tautomer in amide-imidic acid tautomerism
In the section on acid-catalysed hydrolysis of nitriles, this webpage has the following line of reasoning;
...the more stable amide tautomer predominates the (following) equilibrium.
(credit)
How ...
- 1,136
1
vote
0
answers
133
views
Decarboxylation of 2‐cyano‐2‐cyclohexylideneacetic acid [closed]
2‐Cyano‐2‐cyclohexylideneacetic acid (1) is heated and $\ce{CO2}$ is lost:
[
Why is this not formed?
In other words, why do π-electrons move into the ring?
- 109
3
votes
0
answers
53
views
I need to reduce the Nitrile group without affecting the boronic acid. How to do that?
I need to Reduce the Nitrile group (CN) in the (3-cyanophenyl)boronic acid in to a primary amine without disturbing the Boronic acid group.Using LAH can trigger reduction of Boronic group. what are my ...
3
votes
0
answers
241
views
Why aren't nitriles very good electrophiles?
I was wondering why nitriles do not react as electrophiles like carbonyl unless they have to, given that the C-N triple bond is still pretty polarized. The LUMO will be higher in energy than a ...
- 732
1
vote
0
answers
32
views
How could I deduce what this organic compound would be?
For compound D (shown in the figure attached above), how can I deduce its structure?
I understand $\ce{CO2}$ has been produced and thus the compound will no longer have the $\ce{-COOH}$ group ...
- 71
5
votes
3
answers
3k
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{...
- 51
2
votes
0
answers
3k
views
Why do nitrile gloves turn yellow from sweaty hands?
When I take off my nitrile gloves after some hours in the lab, the inside of them has turned yellow. This happens especially in the regions around joints.
I suspect this is due to a reaction between ...
- 424
4
votes
2
answers
3k
views
Why is it aqueous and ethanolic conditions for nucleophillc substitution of cyanide ion with benzyl chloride?
I was doing an exam question where benzyl chloride was undergoing a nucleophilic substitution with cyanide ion to form benzyl cyanide.
Please can someone enlighten me as I have never seen both ...
- 63
0
votes
1
answer
2k
views
Can aromatic rings be cyanated using cyanide as a nucleophile? [closed]
For example, can I convert chlorobenzene into benzonitrile by using potassium cyanide as the reagent?
- 13
1
vote
0
answers
475
views
What is a reasonable mechanism for the following reaction?
Hello all! I'm stuck on this one question and am not sure how to finish the mechanism. What I did was attack the alkyne first with the N farthest to the left. I'm not sure what do to after that though....
- 113
3
votes
1
answer
396
views
Mechanism for the intra-molecular exchange of an ester and a nitrile group
When the isolated product 4 is treated with sodium ethoxide in ethanol it rearranges to 5 as shown:
My TA says that you need to start with a reverse Claisen at the ketone but I am not quite sure ...
- 113
8
votes
2
answers
3k
views
What is the meaning of the word root "aceto"?
What is the meaning of the word root "aceto"?
I believed that "aceto" meant a methyl attached to a carbonyl group. For example, as in acetamide. Then, why do we name $\ce{CH3C\bond{3}N}$ as ...
4
votes
1
answer
513
views
What anions does the loss of a proton from HOCN and HNCO produce? Are they same or different?
What anions does the loss of a proton from $\ce{HOCN}$ and $\ce{HNCO}$ produce? Are they same or different?
Once, I had asked my teacher if $\ce{HCN}$ and $\ce{ HNC }$ are different or same compunds, ...
- 1,218
-3
votes
2
answers
2k
views
Nucleophilic acyl substitution: conversion of butanoic acid to butanenitrile [closed]
How can I convert the carboxylic acid functional group into a nitrile?
- 25
3
votes
1
answer
494
views
Is (cycloprop-2-en-1-ylidene)propanedinitrile aromatic or not?
Is (cycloprop-2-en-1-ylidene)propanedinitrile ((cycloprop-2-en-1-ylidene)malononitrile) aromatic or not? If yes? How?
- 39
6
votes
1
answer
2k
views
Conversion of isonitrile (isocyanide) group into cyanide group?
In an isonitrile (isocyanide) group, the carbon atom has a negative charge (I know that this is due to the lone pair of electrons) instead of the nitrogen atom, but in my point of view, this seems a ...
- 1,226
23
votes
3
answers
12k
views
Why do SN2 reactions of alkyl halides proceed differently with KCN and AgCN?
Alkyl halides react with $\ce{KCN}$ to form alkyl cyanides as the main product, whereas the use of $\ce{AgCN}$ leads to isocyanides as the chief product. Why does this happen?
- 371
15
votes
1
answer
6k
views
Synthesis of mandelic acid from benzaldehyde
For an upcoming exam, I have to describe the synthesis of 2-hydroxy-2-phenylacetic acid (mandelic acid) from benzaldehyde. The provided answers describe quite a long process, consisting of 8 stages. ...
- 335