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Exam 3 Study Guide

by: Courtney Erickson

Exam 3 Study Guide CHEM 2311 P1

Courtney Erickson
GPA 3.5
Organic Chemistry 1

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About this Document

Here's my study guide for exam 3. It covers the important concepts we learned in chapters 7-9 of Klein's Organic Chemistry. This includes an explanation of Substitution reactions, Elimination react...
Organic Chemistry 1
Study Guide
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This 5 page Study Guide was uploaded by Courtney Erickson on Thursday December 10, 2015. The Study Guide belongs to CHEM 2311 P1 at Ball State University taught by Albiniak in Summer 2015. Since its upload, it has received 31 views. For similar materials see Organic Chemistry 1 in Chemistry at Ball State University.


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Date Created: 12/10/15
ORGANIC CHEMISTRY EXAM 3 Exam 3 covers chapters 7 8 9 and 10 Definitions Nucleophile a molecule that donates e39pair this is similar to a base Leaving Group LG a molecule that accepts a pair of e39 from the atom that the nucleophile donated its electrons similar to an acid Type of Alkyl Halide Methyl H3CX 39 Pr1mary 1 1 if EH2 x us CHI a Secondary 2 I a l D an E Haw I Tertiary 3 H E CH1 2 j I r f a Zaitsev Product the more substituted product Hoffman Product the less substituted product lr Mu a H SUBSTITUTION U 5N2 VS 5N1 Main steps Nucleophilic Attack Loss of LG Rate of Rxn based on substrate Me gt 1 gt 2 gt 3 Steric hindrance is an issue Stereochemistry Inversion caused by backside attack Nucleophile Prefers Strong Nucleophiles ex 139 HS39 HO39 Br39 HZS RO39 Cl RSH N E C Solvent Polar Aprotic Solvent ex DMSO DMF i2 3 l l fa quot quotA HMPA Acetonitrile 1 H3CC E N E39nJ lT H ENE All possible steps PT gt LG Loss Nuc Attack gt PT Main steps Loss of LG gt Nucleophilic Attack Rate of Rxn 3 gt 2 gt 1 gt Me Stability of carbocation O is an issue Stereochemistry Forms Enantiomers gt Racemization Nucleophile Prefers Weak Nucleophiles ex 1 H20 ROH Solvent Polar Protic Solvent ex Water Methanol HE G H HI ME quotMI Ha H Ethanol Acetic Acid in E1 In H wquot a H Ammonia Hquot 7 quotENE I H All possible steps PT gt LG Loss gt Rearrange C gt Nuc Attack gt PT ELIMINATION E2 vs E1 Main Reaction PT Loss of LG Rate of Rxn 3 gt 2 gt 1 gt Me Regioselectivity is more important Stereochemistry Antiperiplanar Regiochemistry Zaitsev product favored Reagent Prefers Strong Bases or Strong Nuc Base Main Reaction Loss of LG gt PT Rate of Rxn 3 gt 2 gt 1 gt Me Prefer more stable cations Stereochemistry Trans gt Cis Regiochemistry Zaitsev product favored more stable product is predominant Reagent Really only happens with Weak Nuc Bases All possible steps PT Loss of LG All possible steps PT gt Loss of LG gt C Rearrange gt PT E1cb E1cb means it is a unimolecular elimination reaction like a regular E1 reaction but in this case the cb stands conjugate base The main difference between the two is that E1cb forms a Carbanion instead of a Carbocation Main Steps PT gt Loss of LG opposite order of E1 rxn Because E1cb reactions are uncommon and only happen under a rare set of conditions the carbanion intermediate must be stabilized we don39t really have to worry about these Reagents Substitution vs Elimination Reagent Hiwcleclprhiie Ease 51TH Ease 39 Wea ll Nun Weak Ease Substrate Eitan LIEL AV 1 A quot AA Mechanism With weak Nuc Base the 1 and 2 rxns will be extremely slow Nucleophile Only Reagents Cl IlS39 Ens Br RS39 RSH r Base Only Reagents H39 DBU DBN Strong Nuc 8 Strong Base Reagents OH39 MeO39 EtO39 Weak Nuc 8 Weak Base Reagents H20 MeOH EtOH ADDITION Hydrohalogenation Addition of H and X across a double bond H and Is I Hydration Addition of OH and H across a double bond H an EH Hydrogenation Addition of H and H across a double b Halogenation Addition of X and X across a double bond Halohydrin Formation Addition of OH and X across a DH and in ma ond double bond Dihydroxylation Addition of OH and OH across a double bond DH v D I UH


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