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Organic Chemistry Study guide

by: Savah Notetaker

Organic Chemistry Study guide CHEM 2535

Savah Notetaker
Virginia Tech

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About this Document

In these notes, I compiled what was in my notes, being sure to highlight points i thought was important and leaving out points that didn't seem relevant or seemed like common knowledge.
Organic Chemistry
Jatinder Josan
Study Guide
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50 ?




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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 AOMO 2AO2MO (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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