Organic Chemistry I Biological Emphasis
Organic Chemistry I Biological Emphasis CHEM 3053
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This 4 page Class Notes was uploaded by Stephania Powlowski on Monday October 26, 2015. The Class Notes belongs to CHEM 3053 at University of Oklahoma taught by Ronald Halterman in Fall. Since its upload, it has received 88 views. For similar materials see /class/229274/chem-3053-university-of-oklahoma in Chemistry and Biochemistry at University of Oklahoma.
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Date Created: 10/26/15
Su10 CHEM3053 Practice Problems for final exam RHalterman 4 8 pts Give the expected regioisomeric products of the following reaction 0 M NBr gt hv and heat 3 8 pts The following ether needs to undergo an ether cleavage reaction Provide appropriate reagents and expected initial products for its ether cleavage Provide a concise explanation for any selectivity observed H30 H Xo 6 12 pts Give the expected major product for each of the following reactions Provide a concise justification for your answer HSC IIO 01 equiv H2804 in CHSOH HSCHIO 01 equiv CH30 gt in CH30H 7 12 pts Provide the reagents needed to carry out the following multiple step transformation Give the structure of the product formed after each step ie if you propose 5 steps show 4 intermediate products and the final product hopefully your scheme will be shorter H H H0 H MEN News CH3 H 14 18 pts For the following radical chlorination reaction a Give the structures of the constitutionally unique monochlorination products b If the relative reactivity of the 1 2 3 C H bonds towards chlorine radical is 1 4 5 calculate the relative amounts of the products shown in a c Show the detailed radical mechanism for the formation of the most abundant product in a H30 H H CH3 V h W 02 H30 CH 25 C 3 CH3053 practice final Page 2 Name 15 14 pts a Circle the favored product for the radical monohydrobromination of 1 hexene b explain stabilization of radical by hyperconjugation sketch orbital interactions C Give the mechanism for this reaction H HBr catalytic HOOH Br H Br Olt QLQH QLQH hn and heat H H H 13 26 pts a Give the detailed step by step mechanism for the following reaction include electron movement arrows and show all proton transfers b Provide two explanations for the driving force for the rearrangment for each explanation include a clear description of orbital stabilization of bonds or high energy intermediates c Plot a reaction coordinate energy diagram for this favorable process Clearly label intermediates and likely rate limiting step H catalytic H2804 CH30537Sp09 Page I RLHaltermat Exam 3 Review Sheet The exam will consist of approximately 40 short response questions and 60 medium and longer response questions All questions will be free response no multiple choice In general review concepts first stability of cations acidity then study mechanisms of reactions one step or multiple syn or anti or random additions then review reactions Rework problems on each topic then review reaction ash cards Chapters 89 Substitution and Elimination Reactions of Alkyl Halides Keep in mind the two questions that must be addressed in each case Does the reaction occur after or as the LG departs Does the reaction occur at the surface H elim or at the interior C subst Consider the 4 factors nature of R group leaving group nucleophilebase and solvent Short response topics Use rate law data in support of SNl or 8N2 mechanism Give product racemic or inversion for SNl or 8N2 reactions Give product of elimination reactions with Hofmann or Zaitsef orientation Identify preferred mechanism alkyl group product leaving group nucleophile base or solvent for a given set of competing reactions Preparation of ethers by substitution reactions Longer response topics Justify relative reactivity of 1 2 and 3 and beta branching RX in 8N2 and SNI reactions Justify relative nucleophilicity and leaving group ability in SN reactions also reversibility of substitution reactions Give stepwise mechanism of SNl or E1 reaction Justify solvent effects in SN reactions Justify factors favoring and SNl or 8N2 reaction pathway Justify factors favoring and E1 or E2 reaction pathway Justify why an elimination would favor Hofmann or Zaitsef orientation Justify stereochemistry of E2 reactions anti periplanar orientation of H and X Discuss relative rates of intramolecular substitution reactions to form cyclic products Chapter 10 Reactions of Alcohols Ethers Epoxides Short response topics Reagents and expected products for reactions of ROH with HX TsCl PX3 SOClz CH3053 rSp09 Page 2 Substitution products for reactions of tosylates Productsreagents for dehydration of alcohols HZSO4 Substitution productsreagents for reactions of ethers HX Substitution products for opening of epoxides RLHaltermat Formation and use of RLi and RMgX reagents as nucleophiles in epoxide opening Products of Stille and Suzuki coupling reactions not covered Longer response topics Mechanism for rearrangements to given products from ROH reactions Rationale for unreactiVity of C 0 and C N bonds argue pKa s amp leaving group ability Explain regiochemistry and stereochemistry of epoxide opening under non protonated normal SNZ and protonated conditions SNl like SNZ Multi step synthetic sequences highlighting chemistry from this chapter especially Grignard and epoxide ring opening SN1 SN2 E1 E2 Kinetics 1st Order 2nd Order 1st Order 2nd Order Stereochemistry Racemization Inversion of Products lose Products lose Configuration Stereocenter Stereocenter Rate of reaction Substrate Steric Factors Substrate Some steric controlled by Electronic Factors Hinderance to Nu Electronic Factors effects need H ntermedCstabilit attack Rate ntermed C and leaving group y 3 gt2 gt1 gtM e Megt1 gt2 gtgt3 stability S gt2 gt1 anti peripanar Reactivity 3 gt2 gt1 gtMe Megt1 gt2 gt3 S gt2 gt1 S gt2 gt1 NuBase Conc Low Concentration High Conc Favors Low Base High Base bulky Effects Favors ConcFavors ConcFavors NuBase Strength Effects Weak Nu favors Strong Nu favors Weak base favors Strong nonNu base favors Leaving Group Effects Good Leaving Group Favors Need fair leaving group Good Leaving Group Favors Need fair leaving group Solvent Effects Highly Polar Solvent Favors Charge Separation Low Polarity Solvent Favors Highly Polar Solvent Favors Charge Separation Low Polarity Solvent Favors Elimination in General Favored by low polarity solvent and a high concentration of strong bulky base General for Substitution Reactions CH3X gt 1 gt SN2 SN2 M ixed 20 lt 8 SN1
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