SNAr (Criteria For SNAr) - Lecture Notes | Lecture Note - Edubirdie

University:
York University
Course:
CHEM 2021 | Introductory Organic Chemistry II
Academic year:

2023
Views:

424

Pages:

7
Author:

Niklas

SnAr Good LG Nuc: STRONG NUC: Ring Becomes E+ NO2 Should Be Present Example: F | NO2-C6H4-F + NaCN → CN-C6H4-NO2 + NaF Para position (to LG) F | NO2-C6H4-F + NaNO2 + HCl → O2N-C6H4-F + NaCl + H2O Ortho position (to LG) F | NO2-C6H4-F + NaN3 → N3-C6H4-NO2 + NaF Meta F | NO2-C6H4-F + NaCN → NO REACTION! F | NO2-C6H4-F + NaNO2 + HCl → NO REACTION! NO NO2 group! Criteria for SnAr: Ring should have strong EWG/NO2 LG should be @ ortho or para to EWG Ring should have good LG (F >> Cl > Br) Mechanism: reaction mechanism with arrows showing the movement of electrons Meisenheimer Complex What if NO2 group is in Meta position reaction with NO2 group in meta position No Reaction! Must be ortho or para position Good Nuc: CN- SR- N3- OH- NH2- OR- Grignard Reagent (RMgX) Reactions w/ Pyr. Ortho F | NO2-C6H4-F + NaOCH3 → OCH3-C6H4-NO2 + NaF Meta F | NO2-C6H4-F + NaCN → NO REACTION! Another way to do aromatic substitution is to use BENZYNE (=) Cl | C6H5-Cl + NaOH → C6H5-OH + NaCl NO RXN! → NO NO2 group → NO Pyr.

Related Documents

SNAr (Criteria For SNAr) - Lecture Notes

SNAr (Criteria For SNAr) - Lecture Notes - Page 1

SNAr (Criteria For SNAr) - Lecture Notes - Page 2

SNAr (Criteria For SNAr) - Lecture Notes - Page 3

SNAr (Criteria For SNAr) - Lecture Notes - Page 4

SNAr (Criteria For SNAr) - Lecture Notes - Page 5

SNAr (Criteria For SNAr) - Lecture Notes - Page 6

SNAr (Criteria For SNAr) - Lecture Notes - Page 7

of 7

New Documents from this Course

COOH (X-Halocarbonyls) Synthesis - Lecture Notes

COOH (X-Halocarbonyls) Synthesis - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Substituent Effect On Mechanisim - Lecture Notes

Substituent Effect On Mechanisim - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Amides (Synthesis Of Amides) - Lecture Notes

Amides (Synthesis Of Amides) - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Steroids (Organic Composition With Common Structures) - Lecture Notes

Steroids (Organic Composition With Common Structures) - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Understanding Nucleophile Reactions - Lecture Notes

Understanding Nucleophile Reactions - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Reactivity Of Acid Chlorides - Lecture Notes

Reactivity Of Acid Chlorides - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Convert Chain Form To Fisher Projection - Lecture Notes

Convert Chain Form To Fisher Projection - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Carbohydrates Cn(H2O)m - Lecture Notes

Carbohydrates Cn(H2O)m - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Nucleophilic Anilines - Lecture Notes

Nucleophilic Anilines - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Formation of Hydrates - Lecture Notes

Formation of Hydrates - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Reactivity Of Aldehydes & Ketones - Lecture Notes

Reactivity Of Aldehydes & Ketones - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note

Adding Alkylgroup Alternative (AAA) - Lecture Notes

Adding Alkylgroup Alternative (AAA) - Lecture Notes

York University CHEM 2021 | Introductory Organic Chemistry II

Lecture Note