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 ...
- 21.9k
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 ...
- 42.1k
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,...
- 31.4k
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 ...
- 23k
6
votes
Accepted
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 ...
- 5,532
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 ...
- 44.2k
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 ...
- 17.2k
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 ...
- 4,402
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:...
- 42.1k
3
votes
Accepted
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 ...
- 62.6k
3
votes
Accepted
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 ...
- 23k
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 ...
- 43.2k
2
votes
Accepted
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.
- 802
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 ...
- 62.6k
1
vote
Can a Lindlar catalyst reduce aldehydes, nitriles, and carbonitriles?
For this question :
The Lindlar's catalyst is poisoned by quinoline
,Here since quinoline isn't mentioned the Pd isn't poisoned hence it will act as H2/Pd only.
You may be confused because in various ...
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, ...
- 26.8k
1
vote
Accepted
Mechanism for the intra-molecular exchange of an ester and a nitrile group
Following is a reasonable suggestion for the rearrangement:
- 42.1k
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 ...
- 26.8k
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