Why other benzene derivatives do not undergo nitrosationNitrosation of benzeneRegioselectivity of...
An Undercover Army
How do you make a gun that shoots melee weapons and/or swords?
How did the Luna spacecraft collect samples of the moon and containerize them for return to Earth?
Short story about an infectious indestructible metal bar?
Why doesn't "adolescent" take any articles in "listen to adolescent agonising"?
Rationale to prefer local variables over instance variables?
Error in TransformedField
SQL Server: Covering indexes including all columns?
newcommand: Using one parameter as the default for the other
Does unused member variable take up memory?
The need of reserving one's ability in job interviews
Professor forcing me to attend a conference
What's the best tool for cutting holes into duct work?
hyperref and beamer: Meta Data | 'pdftitle' not Working
What is "desert glass" and what does it do to the PCs?
How can I portion out frozen cookie dough?
What does "rhumatis" mean?
SHA 256 Algorithm
V=IR means causation or equivalence?
Short story about cities being connected by a conveyor belt
Increase the space between numerator and denominator
Was it really inappropriate to write a pull request for the company I interviewed with?
I can't die. Who am I?
Why prohibit private health insurance?
Why other benzene derivatives do not undergo nitrosation
Nitrosation of benzeneRegioselectivity of acid-catalyzed ring-opening of epoxidesNitrosation of benzeneAcidic nature of benzene and other alkenesNomenclature of benzene derivatives with two functional groupsWhy does selenophene not undergo aromatic substitution?Isocyanides undergo addition reactions, but cyanides do not. Why?Thermodynamic stability of benzene derivativesWhy does a Beckmann Rearrangement not occur in the in nitrosation of cyclohexanone?Why ammonium salts can not undergo substitutionDoes CF3COOH undergo decarboxylation ? Why or why not?
$begingroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce{-^+N=O}$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
edited 1 hour ago
Avnish Kabaj
3,65431347
asked 4 hours ago
StarboyStarboy
355
$endgroup$
add a comment |
$begingroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce{-^+N=O}$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
edited 1 hour ago
Avnish Kabaj
3,65431347
asked 4 hours ago
StarboyStarboy
355
$endgroup$
add a comment |
$begingroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce{-^+N=O}$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
edited 1 hour ago
Avnish Kabaj
3,65431347
asked 4 hours ago
StarboyStarboy
355
$endgroup$
Solomon and Fryhle $11 th$ ed :
Most other benzene derivatives except phenols and tertiary aromatic amines do not undergo C- nitrosation reaction.
I agree that if there is a primary or secondary aromatic amine, the reaction will follow other routes but in case of other activating substituents EAS is the only route left for the electrophile $ce{-^+N=O}$ for example with anisole.
Also it seems to contradict ron's answer
So which one is correct?
organic-chemistry amines
organic-chemistry amines
edited 1 hour ago
Avnish Kabaj
3,65431347
asked 4 hours ago
StarboyStarboy
355
edited 1 hour ago
Avnish Kabaj
3,65431347
asked 4 hours ago
StarboyStarboy
355
edited 1 hour ago
Avnish Kabaj
3,65431347
edited 1 hour ago
Avnish Kabaj
3,65431347
edited 1 hour ago
Avnish Kabaj
3,65431347
3,65431347
asked 4 hours ago
StarboyStarboy
355
asked 4 hours ago
StarboyStarboy
355
asked 4 hours ago
StarboyStarboy
355
355
add a comment |
add a comment |
1 Answer
1
active
oldest
votes
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggest to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 2 hours ago
WaylanderWaylander
6,49911424
$endgroup$
add a comment |
Your Answer
StackExchange.ifUsing("editor", function () {
return StackExchange.using("mathjaxEditing", function () {
StackExchange.MarkdownEditor.creationCallbacks.add(function (editor, postfix) {
StackExchange.mathjaxEditing.prepareWmdForMathJax(editor, postfix, [["$", "$"], ["\\(","\\)"]]);
});
});
}, "mathjax-editing");
StackExchange.ready(function() {
var channelOptions = {
tags: "".split(" "),
id: "431"
};
initTagRenderer("".split(" "), "".split(" "), channelOptions);
StackExchange.using("externalEditor", function() {
// Have to fire editor after snippets, if snippets enabled
if (StackExchange.settings.snippets.snippetsEnabled) {
StackExchange.using("snippets", function() {
createEditor();
});
}
else {
createEditor();
}
});
function createEditor() {
StackExchange.prepareEditor({
heartbeatType: 'answer',
autoActivateHeartbeat: false,
convertImagesToLinks: false,
noModals: true,
showLowRepImageUploadWarning: true,
reputationToPostImages: null,
bindNavPrevention: true,
postfix: "",
imageUploader: {
brandingHtml: "Powered by u003ca class="icon-imgur-white" href="https://imgur.com/"u003eu003c/au003e",
contentPolicyHtml: "User contributions licensed under u003ca href="https://creativecommons.org/licenses/by-sa/3.0/"u003ecc by-sa 3.0 with attribution requiredu003c/au003e u003ca href="https://stackoverflow.com/legal/content-policy"u003e(content policy)u003c/au003e",
allowUrls: true
},
onDemand: true,
discardSelector: ".discard-answer"
,immediatelyShowMarkdownHelp:true
});
}
});
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function () {
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f110609%2fwhy-other-benzene-derivatives-do-not-undergo-nitrosation%23new-answer', 'question_page');
}
);
Post as a guest
Required, but never shown
1 Answer
1
active
oldest
votes
1 Answer
1
active
oldest
votes
active
oldest
votes
active
oldest
votes
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggest to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 2 hours ago
WaylanderWaylander
6,49911424
$endgroup$
add a comment |
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggest to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 2 hours ago
WaylanderWaylander
6,49911424
$endgroup$
add a comment |
$begingroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggest to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 2 hours ago
WaylanderWaylander
6,49911424
$endgroup$
Anisole can be nitrosated in good yield reference here. This, and other references, note that the PhOMe group is unstable to the reaction conditions being cleaved to give phenol.
m-Xylene can be nitrosated in good yield, o-xylene and toluene in modest yield in TFA or sulfuric/acetic acid mix under nitric oxide reference here
Nitrosonium tetrafluoroborate will also nitrosate a range of electron-rich aromatics, including anisole and xylenes reference here
This suggest to me that the authors of the textbook quoted are in error, as two of the references predate the publication date of the textbook.
answered 2 hours ago
WaylanderWaylander
6,49911424
answered 2 hours ago
WaylanderWaylander
6,49911424
answered 2 hours ago
WaylanderWaylander
6,49911424
answered 2 hours ago
WaylanderWaylander
6,49911424
6,49911424
add a comment |
add a comment |
Thanks for contributing an answer to Chemistry Stack Exchange!
- Please be sure to answer the question. Provide details and share your research!
But avoid …
- Asking for help, clarification, or responding to other answers.
- Making statements based on opinion; back them up with references or personal experience.
Use MathJax to format equations. MathJax reference.
To learn more, see our tips on writing great answers.
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
StackExchange.ready(
function () {
StackExchange.openid.initPostLogin('.new-post-login', 'https%3a%2f%2fchemistry.stackexchange.com%2fquestions%2f110609%2fwhy-other-benzene-derivatives-do-not-undergo-nitrosation%23new-answer', 'question_page');
}
);
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Sign up or log in
StackExchange.ready(function () {
StackExchange.helpers.onClickDraftSave('#login-link');
});
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Sign up using Google
Sign up using Facebook
Sign up using Email and Password
Post as a guest
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
Required, but never shown
