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Introductory Organic Chemistry

by: Ms. Jerrell Lind

Introductory Organic Chemistry CHEM 343

Marketplace > University of Wisconsin - Madison > Chemistry > CHEM 343 > Introductory Organic Chemistry
Ms. Jerrell Lind
GPA 3.55

Ieva Reich

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Ieva Reich
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This 7 page Class Notes was uploaded by Ms. Jerrell Lind on Thursday September 17, 2015. The Class Notes belongs to CHEM 343 at University of Wisconsin - Madison taught by Ieva Reich in Fall. Since its upload, it has received 33 views. For similar materials see /class/205342/chem-343-university-of-wisconsin-madison in Chemistry at University of Wisconsin - Madison.


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Date Created: 09/17/15
Discussion Problems for Mar 3 4 1 For each of the following reactions give the elimination products if the products can exist as stereoisomers show which stereoisomers are obtained in 3D 283S 2 chloro3methylpentane with high conc of NaOCH3 b 283R2 chloro3methylpentane with high conc of NaOCH3 2R382 chloro3methylpentane with high conc of NaOCH3 d 2R3R 2 chloro3methylpentane with high conc of NaOCH3 3chloro3ethyl22 dimethylpentane with high conc of NaOCHZCHS 2 Propose a mechanism to account for the formation of all three products Show electronpushing arrows and all intermediates OBr CHSCHZOH f OO 39 o 3 is 4 quot 39 39iexai lUl and trans 4 39iexai lUl formed different substitution products but the 1 same elimination product 39OH HO Br Ho OmHOH HO OH O a Explain by showing the mechanisms why different substitution products are formed b Draw the stereoisomers formed by elimination in 3D 4 cis lBromo4tertbutylcyclohexane and trans1bromo4tertbutylcyclohexane both react with NaOCHZCHs to give 4tertbutylcyclohexene Explain why the cis isomer reacts much more rapidly than the trans 5 Three substitution products and three elimination products are obtained from the following reaction Explain mechanistically by using electronpushing arrows and intermediates how each is formed 0 CH3 CH3 CH3 c 3 OCH3 H CH3 CH3 Br OCH3 CH3 OCH3 3 CH3 CH3 CH3 CH3 6 Consider the following reactions Identify the product in each case Cl t l MOH amp 06H1ZO basic CHSOH Cx H 0 g C6H120 PLT cchem 343 and 345chem 34334309sproblemsdiscussion6plt 03022009 Scale 070 SFN Chem 34313451547 Reich Redox at Carbon Atoms It is not as easy to de ne oxidation level at carbon as it is for transition metals Almost all the compounds we are interested in formally have 8 electrons around each carbon Removal of hydrogen atoms from a compound is oxidation and addition of hydrogen atoms is reduction but for proper consideration of oxidation level carbons must be considered in pairs 7 On this sheet R is an alkyl or aryl group or an H atom Y is a quotheteroatomquot to the right of C in the Periodic Table Y atoms have lone pairs if they are formally neutral The impoth groups are Cl Br 1 OR SR and NR2 M is an alkali metal Li No or K To determine the oxidation level of a C2 unit count up the number of robonds mos the number of C Y bonds the quotsumquot The most reduced compounds have mm zero and the bigger sum is the more oxidized the C fragment is Most of compounds we will be discussing have sum equal to 03 Some examples for C compounds are shown below Sum 0 1 2 39 3 H3CCHzM H3CCH2Y H2CCHY H3CCEN 113031213112 H3CCH20H Yugocry u20cr2 H3CCHZBr H3CCHY2 YCHCHY rigCH3 ireCH3 o o Oxidation Reduction Going from one sum level to another involves redox chemistry Increasing sum requires an oxidizing agent and decreasing sum a reducing agent Replacement of an M group like H or Li by a Y group like OH Br NH2 is oxidation the reverse reduction Addition of YY reagents such as BrBr OHOH BrOli to double bonds is oxidation and elimination of these is reduction On the other hand addition of M M reagents such as HH HBR2 is reduction and elimination of MM is oxidation r Going up or down a column at one sum level involves acidbase chemistry deprotonation replacement of one M group such as H by another such as Li or 8R2 nucleophilic substitution of one Y group by another Br by OH Cl by NHZ et c elimination or addition of HY such as H NHZ HCl H Br liOH HOClI3 HSH 39 If you can identify a given reaction as either acidfbase or redox then it is easier to select an appropriate reagent suitable for the task On the other hand given a starting material and a reagent if you can classify the reagent as either acidbase oxidizing or reducing then it is easier to determine an appropriate product Reagents by Redox and AcidBase Classes Oxidizing Agents Free Radicals Cl39 Br 139 Cl39 and Br both add and abstract H Compounds with 00 bonds PhCOOOC0Ph tBuOOtBu free radical initiators 03 RCO3H H202 02 Halogen molecules and related species C12 Brz 12 ClOH BrOH add to 1 bondS Metals in high valence states KMnO4 CrVl reagents Os0394 NalO4 MnOz FeIII CuII Agl Reducing Agents Hydrogenation Hzcatalyst transition metals esp Pd Pt Ni Metals K Na Li Mg Zn Hydride Donors BZHG LiAlH4 NaBH4 Inorganic Reducing Agents Bisulfite NaHSO3 Hypophosphorous acid H3P02 Thiosulfate NaZSZOQ NucleophilesBases Anionic V Carbon Centered RLi RMgX R2CuLi NaC139 Nitrogen Centered iPer39Li HZN39M N3 Oxygen Centered RO39 HO39CH3COO39 Sulfur Centered RS39 NECS39 Halogens Cl39 Br39 139 Neutral R3N H3N ROH H20 Acids Mineral Acids Strong Organic Acids RSO3H CF3C02H Camoxylic Acids RCQZH 39 Weaker Organic Acids HCN ROH Basicity nucleophilicity and reducing power do tend to go together electrons are given up39in all three cases Good nucleophiles like I39 and RS can give up one electron to an easily reduced compound as well as act as nucleophiles making YC bonds In the sarne vein acidity and oxidizing power are related Some strong acids like HCIO4 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