Organic Chemistry Study guide
Organic Chemistry Study guide CHEM 2535
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This 22 page Study Guide was uploaded by Savah Notetaker on Monday September 19, 2016. The Study Guide belongs to CHEM 2535 at Virginia Polytechnic Institute and State University taught by Jatinder Josan in Summer 2016. Since its upload, it has received 11 views. For similar materials see Organic Chemistry in Chemistry at Virginia Polytechnic Institute and State University.
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Date Created: 09/19/16
Organic chemistry study guide Things to cover Valence bond theory Molecular orbital theory Hybridization Molecular structure Molecular polarity Atoms have atomic orbitals combine Molecular orbitals Polarity of bond Molecular polarity Draw Lewis dot structures H H + H H H H HH 2 2 F2 F + F F F Draw Kekule Structure Ammonia F2 FF H N H H N H F F H H Octet Rule: NonBonding electrons (NBE) + Bonding electrons (BE)=8 total Main row elements Formal Charges (FC) FC= #VE(NBE+1/2BE) FC= 1(0+1/2(2))=11=0 FC= 3(0+1/2(6))=33=0 FC= 4(2+1/2(6))=45=1 FC=0 Bond number 1 bond: H Single Bonds F Cl 2 bonds: O O Double bond 3 bonds: N N N Triple bond 4 bonds: C C C C Bond polarity and dipole mom ) = Size of charge X distance between charges (Bebye units D) HC HF CMg 0.4 D HBv 0.8 D = 0 D Atomic orbitals (AO) and molecular orbitals (MO) Orbitals Spatial distribution of electrons (0, 1, or 2) Types or orbitals: s, p, d, and f Why do bonds form? A molecule is more stable than an atom Electrons can occupy more volume by sharing the 2 nuclei Greater attraction between electrons and multiple nuclei AOMO 2AO2MO (bonding and anti bonding) Hybridization of AOs C 4VE 1s 2px 2y zp 4AOs 3 1s 2px 2py 2z 4sp 4 hybrid sp 3 H 2 = CH 2 p x py pz s s + 2p 3sp 2 1(s bond) 2 (p bond) 3 (sp bonds) Ethyne HC HC s x p y p z p sp HF HCl HBr HI Shortest Longest BronstedLowry [Proton transfer] Acid: donates a proton HCl Base: accepts a proton OH Lewis AcidBase LA: accepts electron pair LB: donates electron pair HCl + H O2 C + H O H pka =7 H pka=1.7 A HCl Cl H 2 H O H H Curved Arrows Factors affecting pka 1 . Electronegativity C<N<O<F CH <4H <H 3<HF 2 Atoms of the same size strongest acid is the one with the most electronegative atom 2 . Size of atom Strongest acid has proton attached to the longest atom 3 . Charge Stronger acid has proton attached to positively charged atom Hybridization 2 3 More sp > sp > sp Electronegative Substituents Resonance Nomenclature ** CH 3HCH CH 2CH 2 3 CH 3H CH2CH CH 2 3 Cl Cl Pentyl chloride ICH 2C 1⁰ carbon CC 2⁰ CCC C 3⁰ CCC C 4⁰ CCC C How to name: #1 Identify the longest chain (called the parent chain) #2 Number the chain in the direction that give the substitution as low number as possible CH 3H CH 2CHCH2CH CH 2 2 3 H 2H CH 2CH 2 3 4propyloctane 4(1methylethyl)octane CH 2CH 3 CH 3 CH C3 CC3 CH CH2HCH2HCH CH 2CH 3 CH CH 2 3 CH 2CH 3 CH C3 CH2H CHCH C2 CH 2 2 3 3 3 3 Functional groups 3ethyl4methylcyclopentane Substituent Functional group CH 3 OH Cl, Br NH 2 ROR O CH Takes first priority 1,2dimethoxyethane ** Iondipole interactions Dipoledipole Hbond HN HO HF Van der Waals interactions Newman projector The eclipsed for has the most torsion strain Torsional: repulsion among electrons in different groups as they pass each other during bond rotation Steric: repulsion between electrons in different groups, but cannot be lessened by bond rotation Angle: bond angles differ from ideal geometry With more CC bonds, there is less strain such as cyclohexane. All CH bonds are staggered Twist boat is at the local energy minimum the diagram in chairchair interconversion of cyclohexane Compound name Asymmetric carbon Stereo center 3 groups present on given carbon All 4 groups must be different to be asymmetric How to draw enantiomers Perspective formulas 2 single lines: in plane Dashed line: back Solid wedge: front Fischer Projections Horizontal line: front Vertical line: back Intersection: asymmetric carbon Types of Isomers Identical compound can be determined if two compounds that are both S or R configure Constitutional isomer Stereoisomers Functional Positional isomers Diastereomers Enantomers Group (includes cis/trans Ex: CH C3 OH 2 Ex: CH C3 CH 2H Cl2 2 isomers) CH O3H 3 C3 CHC2 3 Fischer Molecules with multiple asymmetric carbons 2 possible stereoisomers n= # of asymmetric carbons Diastereomers Fischer projection, longest chain on vertical line, are in eclipsed conformations (2S, 3S) 3 bromobutan2ol 2 asymmetric Centers: 3 stereoisomers (a meso compound and a pair of enantiomers) Eisomer (Epposite) Zisomer (Zame)
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