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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Reaction of DIBALH with alkyl cyanides

I was recently studying reactions involving DIBALH (diisobutyl aluminium hydride) and saw that it's reaction with alkyl cyanide yielded R-CH2NHOH according to Jerry March whereas in Solomons the ...
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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
85 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 ...
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1answer
214 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?
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168 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
103 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 ...
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2answers
1k 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
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1answer
157 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
742 views

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
75 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
885 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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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. ...