16 votes
Accepted

What is the meaning of the word root "aceto"?

The root "acet-", according to wiki, is derived from latin acētum, meaning vinegar, i.e. diluted acetic acid. Consequently, direct derivatives of acetic acid, like acetamide and acetonitrile are ...
permeakra's user avatar
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15 votes
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Why do SN2 reactions of alkyl halides proceed differently with KCN and AgCN?

The cyanide anion is an example of an ambident nucleophile, these are nucleophiles which, usually due to delocalisation, are able to attack an electrophile from two or more atoms. In the case of the ...
NotEvans.'s user avatar
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12 votes

Why do SN2 reactions of alkyl halides proceed differently with KCN and AgCN?

The different reactivities of $\ce{KCN}$ and $\ce{AgCN}$ with alkyl halide, giving nitriles and isonitriles, respectively, has often been cited as a prime example of Pearson’s hard and soft acids and ...
Jan's user avatar
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10 votes
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Conversion of isonitrile (isocyanide) group into cyanide group?

Isonitriles will, given the correct conditions, spontaneously transform into nitriles. The reaction mechanism is very interesting; it is basically a cationic [1,2]-migration of the $\ce{R}$ group ...
Jan's user avatar
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8 votes

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

My answer is intended to support Waylander's suggestion elsewhere. I thought it'd be better to give OP some insight of this reduction mentioned (Ref.1). To my knowledge, after doing thorough ...
Mathew Mahindaratne's user avatar
7 votes

On the stabler tautomer in amide-imidic acid tautomerism

The relative stability of the two tautomers (two isomers differing how protons are bound) may be assessed from the equilibrium constant you may formulate for the two. Deriving from above illustration,...
Buttonwood's user avatar
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6 votes
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What anions does the loss of a proton from HOCN and HNCO produce? Are they same or different?

When they are bonded to hydrogen that is $\ce{HOCN}$ $\ce{HNCO}$. The two compounds will be different: From Wikipedia Organic cyanates are called isocyanates when there is a $\ce{C−NCO}$ bond and ...
Avyansh Katiyar's user avatar
6 votes

Selective reduction of nitro group to amine, in benzene ring containing nitrile?

$\ce{SnCl2.2H2O}$ in refluxing $\ce{EtOAc}$ as reported by Bellamy & Ou here will do this very cleanly. Work up into ice then add concentrated $\ce{NaOH}$ until you get phase separation. I have ...
Waylander's user avatar
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4 votes

Is (cycloprop-2-en-1-ylidene)propanedinitrile aromatic or not?

At least formally, the target compound is the product of a Knoevenagel reaction of cyclopropenone with malononitrile. For cyclopropenone, a zwitterionic mesomeric structure is conceivable. This ...
Klaus-Dieter Warzecha's user avatar
3 votes
Accepted

Naming a nitrile in the middle of an aliphatic chain

Compounds like this are named based on the nitrile from which they are derived. So, in your case, the nitrile is propanenitrile: $$\ce{CH3-CH2-C#N}$$ A protonated nitrile would be called a nitrilium ...
Ben Norris's user avatar
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3 votes

Why is it aqueous and ethanolic conditions for nucleophillc substitution of cyanide ion with benzyl chloride?

The cyanide ion is a very good nucleophile and reacts readily with benzyl chloride. The problem is that the cyanide salts are soluble in water, while the benzyl chloride is not. Therefore, ethanol ...
Raoul Kessels's user avatar
3 votes

Why is it aqueous and ethanolic conditions for nucleophillc substitution of cyanide ion with benzyl chloride?

Since $\mathrm{p}K_\mathrm{a}$ of $\ce{HCN}$ is 9.21 (Wikipedia), the cyanide ion in water is pretty alkaline and contains significant amounts of hydroxide ions, according to the following equilibrium:...
Mathew Mahindaratne's user avatar
3 votes

Nucleophilic acyl substitution: conversion of butanoic acid to butanenitrile

The direct conversion of a carboxylic acid to a nitrile is not a well defined reaction, although examples do exist, the reaction is not general to a wide range of carboxylic acids. By far the most ...
NotEvans.'s user avatar
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3 votes
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Acidity of Benzenepropanenitrile

I would have called it 3-phenylpropanenitrile, but let's get to the real chemistry here. Clearly the candidates for most acidic hydrogen atom are those on the saturated carbon atoms between the phenyl ...
Oscar Lanzi's user avatar
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3 votes
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Why is S-alanine acetylated in the synthesis of S-cathinone?

The treatment of N-acetyl-S-alanine with PCl5 gives the acid chloride of the carboxylic acid and converts the N-acetyl group to the imidoyl chloride. This species undergoes classical F-C acylation ...
Waylander's user avatar
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2 votes

Reaction of Grignard reagent with hydrogen cyanide

A Grignard reagent will certainly react with water to form a hydrocarbon, and based on $pK_a$ values $\ce{HCN}$ is a much stronger B-L acid than water. While a nucleophilic attack on the cyanide ...
Oscar Lanzi's user avatar
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2 votes
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Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?

There is just a silly mistake. As TRC told, $\ce{Pd/C}$ is not a Lindlar catalyst and it behaves as a normal $\ce{Pd/H2}$. Refer to the link for more information.
Jay's user avatar
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1 vote

Nucleophilic acyl substitution: conversion of butanoic acid to butanenitrile

Carboxylic acid can be converted to nitriles using various methods: Direct Preparation of Nitriles from Carboxylic Acids in Continuous Flow A continuous-flow protocol for the preparation of organic ...
Nilay Ghosh's user avatar
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1 vote
Accepted

Can aromatic rings be cyanated using cyanide as a nucleophile?

Chlorobenzene is generally inert to nucleophilic substitution. It was observed by Rosenmund and Braun that using an ethanolic solution of potassium cyanide and cuprous cyanide as catalyst at 200°C, ...
Nilay Ghosh's user avatar
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1 vote
Accepted

Mechanism for the intra-molecular exchange of an ester and a nitrile group

Following is a reasonable suggestion for the rearrangement:
Mathew Mahindaratne's user avatar

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