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CEM 251 Final Exam Study Guide

by: Sarah Struble

CEM 251 Final Exam Study Guide CEM 251

Marketplace > Michigan State University > Chemistry > CEM 251 > CEM 251 Final Exam Study Guide
Sarah Struble
GPA 3.95
Organic Chemistry I
C. Vasileiou

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About this Document

Includes: Calculating Formal Charge, Bonding, Naming, Stereochemistry, Numbering Rules, Newmann and Fisher Projections, Cycloalkanes and Chair Structures, ALL Reactions (SN1&2, E1&2, All Addition...
Organic Chemistry I
C. Vasileiou
Study Guide
50 ?




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This 7 page Study Guide was uploaded by Sarah Struble on Monday December 14, 2015. The Study Guide belongs to CEM 251 at Michigan State University taught by C. Vasileiou in Fall 2015. Since its upload, it has received 220 views. For similar materials see Organic Chemistry I in Chemistry at Michigan State University.


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Date Created: 12/14/15
Page 1 of 7 CEM 251 Final Exam Study Guide Calculating Formal Charge Valence Electrons Nonbonding electrons lone pairs Electrons in bonds 1 e per line H 1391 H N H l H quot H H 4 valence electrons 2 lone 5 valence electrons zero electron electrons 3 bonds 1 lone pairs 4 bonds 1 Bonding Sp3 Carbons only have single bonds sigma bonds Sp2 Carbons have at least one double bond Sp Carbons have at least one triple bond Single bond one sigma bond Double bond one sigma bond one pi bond Triple bond one sigma bond two pi bonds Naming C Prefix Bonding suffix 1 meth only sigma ane 2 eth double ene 3 prop triple yne 4 but sp3 C X ide 5 pent O H anol 6 hex 7 hept groups off of the carbon chain get suffix yl 8 oct number the chain so that groups off of carbon chain get lowest numbers 9 non double bonds should be lowest possible number 10 dec ring structures get prefix cyclo Stereochemistry 3D Structure Chirality group pointing up or down asymmetry asymmetric carbons chiro hand mirror images but cannot be super imposed Chiral Carbon 0 chiral center can only be sp3 carbons Any time you have a carbon with 4 DIFFERENT groups on it it is a chiral carbon H C m b H gt 4 of the same groups around C so it is NOT CHIRAL Once you find the chiral C number the groups around the carbon Numbering Rules Priority is based on atomic number highest atomic number first priority only number atoms directly bonded to the chiral C see which way the priority numbers increase clockwise or counterclockwise Two Types of Chirality R or S CWCCW 4 Priority Atom dashwedge Chirality CW back dash R CW front wedge S CCW back dash S CCW front wedge R Enantiomers two chiral molecules whose stereocenters are all opposite Identical molecules two molecules with all the same stereo centers Diastereomers some stereocenters are different but not all To find the number of stereoisomers a molecule has n number of C n number of stereoisomers Newmann Projections H H H HH H H W staggered Elipsed more stable less stable Page 2 of 7 Page 3 of 7 H H N 3 staggered gt Anti CH A 3 H O H CH Fisher Projectons vertical line dashed horizontal line wedge LL KQCQ tarcw gt ex t Cycloalkanes M LL I trans equatorial bonds dashed bond axial bonds wedged bond most stable chair structure is when the biggest groups are equatorial Page 4 of 7 ctins Nucleophiles electron rich species neg charge give electrons ex lone pair negative charge double bond 00 quote A K 2R R 9 E Electrophiles electron poor species pos charge take e ex positively charged partial pos charge J H L ES AW SN2 Reactions happen in aprotic solutions CH3Xgt1 gt2 gtgtgt3o oH SN1 Reactions 3 gtgt2 gtgtl 1 methyl not allowed 2 can do BOTH SN1 and SN2 gt if weak Nuc with polar protic solvent H20 alcohol SN1 E1 Reactions H20 H E2 Reactions tBuOK DBN DBU H X Addition H Cl H Br etc X goes to more substituted C X2 Addition Br2 Cl2 NBS rxn Brz Br U IlBr Page 5 of 7 X2 H20 Addition Br2 H20 NBS H20 OH goes to more substituted Carbon Hydration H OH Addition H20 H H20 H2804 1 HgOAc2 H20 2 NaBH4 OH goes to more substituted Carbon Hydration H OH AntiMark Addition 1BH3 2H202 OH goes to less substituted Carbon RO H Addition ROH H 1HgCAc2 ROH 2 NaBH4 1HgSO4 ROH 2 NaBH4 H2 Hydrogenation H2 PdC H2 Pt02 syn addition product is cis both H s are wedge or both are dash Addition of O syn Epoxidation mCPBA rxn mCPBA V gt Dihydroxylation syn Addition 1 OsO4 2NaHSO3 OH and OH both dash or both wedge OH 1 OsO4 2NaHSO3 V OH Cleavage 03 Ozonlysis using ozone to break a double bond 1 O3 2 ZnH 39 39 HAo 0 01 Ga Page 6 of 7 Cleavage with KMnO4 if you have an H on the double bond that H will also get an O Viol Synthesis 0 g only has 2 0 3 but pdt has 3 First step should be to deprotonate the alkyne and add a C H 1 NaNH2 1 BH3 0 H A gt 2 CHSBrI 2 H202 I C r 399 SN2 L7 to get the carbonyl on terminal C the rxn needs to be antiMark OH goes on less subst C RDB 2n 2 H s X s 0 does nothing 0 2 N adds one 8 adds one SPQ More Naming39 3 39 3 SP lo X p X X X phenyl group vmyl group benzyl group Page 7 of 7 Types of lsomers Constitutional lsomers Structural isomers Functional group isomers W Stereoisomers conformational ring flip configuration cistrans chirality isomers SIR


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