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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0answers
18 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 (...
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1answer
40 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 ...
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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, ...
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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 ...
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1answer
92 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 ...
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0answers
62 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?
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39 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 ...
2
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0answers
104 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 ...
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30 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 ...
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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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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 ...
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2answers
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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 ...
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1answer
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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?
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378 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....
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1answer
220 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 ...
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2answers
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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 ...
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1answer
380 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, ...
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2answers
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Nucleophilic acyl substitution: conversion of butanoic acid to butanenitrile [closed]

How can I convert the carboxylic acid functional group into a nitrile?
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1answer
227 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?
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1answer
1k 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 ...
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3answers
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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?
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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. ...