Three Types Of Electrophiles - Lecture Notes | Lecture Note - Edubirdie

University:
York University
Course:
CHEM 1000 | Chemical Structure
Academic year:

2021
Views:

57

Pages:

3
Author:

Niklas

3 Types of Electrophiles: All must have an empty orbital that is low in E. 1. Proton (H+) Empty 1s orbital 2. π-Electrophiles (empty p or π* orbital) R | R-C=C-R | R R | R-C=C-R | R+ Examples: E+ :O: ←→ E-O E+ :N≡N: ←→ E-N≡N+ 3. σ-Electrophiles (low lying σ* orbital) H-Br H-C-Br | H H-C-Br | H+ Involves loss of a LG! R-C≡C-R | R R-C≡C-R | R+ Break bond Example: Me | Me-C=C-H | Me π-nucleophile π-electron (C=C) Basic Mechanistic Processes (Bonds Break & Forming) 1. Nucleophilic Attack: donation of e- from Nuc. to Elect. Bond Formation Me | Me-C-Cl | Me Me | Me-C-Cl | Me π-electrophile Example: CARBONYL ADDITION RXNS Bond Forming H | H-C=O Bond Breaking H | H-C=O 2. Loss of Leaving Group Involves formation of two species via cleavage of a σ bond. Br | Me-C-Me | Me Me | Me-C+ | Me + Br- Leaving Group (LG) 3. Proton Transfer (Fastest Process) H-O-H H | H-C-H | H 4. Cation Rearrangements: 1°, 2°, 3° Increasing Stability ΔG = -ve

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