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Week 5 Chem 333

by: Hayley

Week 5 Chem 333 CHEM 333 001

GPA 3.35
Organic Chemistry I
John Lavigne

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About this Document

These are from notes from in class from the week of 9/21-9/25 of Organic Chemistry.
Organic Chemistry I
John Lavigne
Class Notes
25 ?




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This 4 page Class Notes was uploaded by Hayley on Sunday September 27, 2015. The Class Notes belongs to CHEM 333 001 at University of South Carolina taught by John Lavigne in Summer 2015. Since its upload, it has received 47 views. For similar materials see Organic Chemistry I in Chemistry at University of South Carolina.

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Date Created: 09/27/15
AcidBase Reactions All about stability of the charged species What atom is the charge on 0 Equilibrium lies towards the weaker acid How to push rxn towards product Excess reactant o LeChatlier Principle How to pull rxn towards product Remove product 0 LeChatlier Principle 0 Distillation and Precipitation For resonance you need M orbitals looks like a gure 8 Factors that impact pKa stability of a charged species 0 Electronegativity Size polarizability Resonance 0 Induction sigma bonds 0 Hybridization there are two trends we need to look at comparing atoms in the electronegatiVity and in the size 1 Electronegativity 0 Definition How willing the atom will be to accept a new electron m pKa Electronegativity CH3OH a CH3O39 H 16 most CH3NH2 e CH3NH39 H 38 CH3CH3 e CH3CH239 H 50 least more electronegatlve atoms are the more ac1d1c H more electronegative atoms are the more acidic the conjugate acid is because it wants electrons which makes it a more stable anion But trend but size does 2 Size Column pKa Electronegativity Size HF 9 F39 2 More Small HCl 9 Cl39 6 HBr 9 Brquot 8 HI 9 I39 9 Least Large For example F 9 electrons owned l electron added 10 electrons a smaller atom 139 53 electrons owned 1 electron added 54 electrons a larger atom The uorine has a bigger change than the Iodide A 1011 change versus a gt2 change Therefore HF is a weaker acid If acidity were explained by electronegatiVity then HF would be more acidic than HI since I is more stable than F then HI is the stronger acid because HI is more likely to give up its proton compared to HF Lavigne said not to worry about going in between rows and columns It s like comparing apples to steak Sum up of these two points compares atoms in same is for comparing atoms in the same 3 Resonance 313 system 0 Delocalizing J13 electrons spread out electrons More acidic because it s delocalizing J13 electrons Example pKa 16 CH3CH20H e CH3CH2039 H 45 CH3COOH e CH3COO39 H 4 Induction 0 system Not as affective at spreading out electron density out as resonance 0 Polarized bonds 0 Is distance dependent 0 Further away less force is exerted in charge I Example magnets 0 Think of it as sucking electron density through sigma system pKa 45 CH3COOH 9 CH3COO39 28 ClCHzCOOH 9 ClCHzCOO39 Why is the 2nd one less than 45 Because of same resonance and same atoms not EN size A dipole is created Cl Recap from Monday 1 Electronegativity for ROWS 0 More electronegative more acidic Increase electronegativity increase acidity lower pKa 2Size of atom Columns 0 Charge increase in size increase in acidity lower pKa 3 Resonance must have P orbitals not distance dependent 4 Induction sigma pathway 0 delocalization of electrons between nuclei Less affective at electron delocalization compared to resonance 0 Polarizationdipole 0 Distance dependent 0 Electron withdrawing groups EWG o Stabilizes negative charge 0 ClBrI EN vs CH 0 Electron donating groups EDG o Stabilizes cations positive charge 5 Hybridization of S character makes a difference pKa Hybridization S character H3CCH2 50 Sp3 25 H3CCH2 40 Sp2 33 H3CECH2 25 Sp 50 more S charactercloser to nucleus positive Source Lewis Base LB 0 Lone pairs pi bonds Sink Lewis acid LA 0 H CJr B Al Polarized Bond Think All organic chemistry rxn s are acidbase rxn Chapter 4 Isomers Constitutional same molecular formula different connectivity conformational same molecular form and same connectivity but different orientation in space 0 Interconvert by simple bond rotation Coplanar in plane of paper exclude wedge and lines Different orientation in space 9different 3D structure EX Ethane C2H6 or H3CCH3 Newman Projection 0 Looking down at carboncarbon bonds 0 Staggered far away 0 Eclipse 0 Typical rotation step 60 0 HCH anglelO95 Staggered has a lower energy vs eclipse 0 In a eclipse repulsion of electrons is present so they want to get away from each other more energy being used 0 Torsional strain HCH angle deviates from preferred Its different so there an increase in energy Rotational Itinerary ALKANES as energy increases Eclipse 0 120 240 360 Staggered 60 180 300 Dihedral Bond Angle energy difference is l kcalmol What about double bonds They don t stagger and eclipse as much so don t worry about them


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