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.

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23 votes
3 answers
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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?
Mohd Shakib's user avatar
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. ...
avramov's user avatar
  • 335
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 ...
Abhishek Bansal's user avatar
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 ...
Khan's user avatar
  • 1,226
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
795 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 ...
harry's user avatar
  • 1,134
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 ...
daniel's user avatar
  • 63
4 votes
1 answer
534 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, ...
Iceberry's user avatar
  • 1,218
3 votes
1 answer
539 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?
Paras Sharma's user avatar
3 votes
1 answer
407 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 ...
Eli Lawrence's user avatar
3 votes
0 answers
437 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 (...
Prajwal Tiwari's user avatar
3 votes
0 answers
76 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 ...
Juan Perez's user avatar
3 votes
0 answers
56 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 ...
Kasun Wekasinghe's user avatar
3 votes
0 answers
253 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 ...
sweetandtangy's user avatar
2 votes
0 answers
42 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 ...
user avatar
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 ...
DK2AX's user avatar
  • 424
1 vote
1 answer
185 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. ...
Samuel Wango's user avatar
1 vote
1 answer
1k 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 ...
Jay's user avatar
  • 804
1 vote
0 answers
44 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 ...
Bree's user avatar
  • 11
1 vote
0 answers
142 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?
rdx's user avatar
  • 109
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 ...
User1265's user avatar
1 vote
0 answers
484 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....
Eli Lawrence's user avatar
1 vote
1 answer
310 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 ...
harry's user avatar
  • 1,134
0 votes
1 answer
86 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, ...
harry's user avatar
  • 1,134
0 votes
1 answer
766 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 -...
newbie105's user avatar
  • 397
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?
SLADE's user avatar
  • 13
0 votes
0 answers
255 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 ...
Tasmay Tibrewal's user avatar
-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?
user43537's user avatar
-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.
Pupz's user avatar
  • 1