Qualitative Analysis Of Acidity - Lecture Notes | Lecture Note - Edubirdie

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

2021
Views:

115

Pages:

2
Author:

Niklas

Qualitative Analysis of Acidity X-H -> X(-) + H(+) Factors affecting acidity: Stability of conjugate base (X-) Resonance Induction (through bond donation/removal of e-) Orbital Housing e- in CB Bond Strength Solvent Atoms: MORE electroneg. atoms BEAR neg. charge MORE willingly Able to pull e- closer & ↓ E of sys. Does not apply to HF or HX in general H-F (vs) H-Cl pKa 3.2 pKa -7 Neg charge on O is more stabilized than the neg charge on N H-N (vs) H-O H H HI is stronger acid than HF. Resonance: Stabilizes CB More Stable CB = More Acidic Acid Induction: Add'n of e-l ↓ pKa H-C-C-C-OH H H H pKa = 3.75 Cl-C-C-C-OH H H H pKa = 2 Cl-Cl-C-C-OH H H H pKa = 1 *EWG: Lower pKa Heteroatoms, sp/sp² Halogens, -NO2, -CN *EDG: Higher pKa Orbitals: sp3 sp2 sp Smaller pKa More Acidic

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