351 E3p key F09

351 E3p key F09 - Chem 351 Name K E Nielson Practice Exam 3...

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Unformatted text preview: Chem 351 Name K E. Nielson Practice Exam 3 Show answers clearly/cross out any answers you don’t want graded. Draw structures when possible with written answers. You may use molecular models. 1. Name the following structures using acceptable IUPAC names, unless the common name is requested. Remember to include stereochemistry when necessary. a. CH3 QH Name E: kWUZ/Wffl Z" 3:IC1 Common name 36' C Jamil/6g M g I: [Q4 2. The pKa of t—butanol is 18 while the pKa of a sp3-hybridized hydrocarbon is around 50. Yet t-butoxide is a strong enough base to pull of a Iii-hydrogen from the sol-hybridized carbon of ethyl brornide. Briefly explain why. EVA __ _ G3 ——l—o\_k natal-lo @11- —\—0Q 'Hrlrgo [33 Cucfiga Jr R753 auras; +7 Ry? 530 Chews—EV + +00 "*9 CHZZCH; “L *i—QHl’BBVQ gecwgim fiHi—igfn (‘ v— Cflw ELM LL. flVVH“E>?/fl “K ) M {Am Meg? val Cam oldecaficsegfl Q23; WSW }. WW 3. Predict the major organic products in the following reactions. Show stereochemistry where necessary. You need only show one enantiomer and write “+ enantiomer” if the product exists as a racemic or partially racemic mixture. Indicate under the product whether the mechanism is 8N2, SNl, E2, or E1. 3- Pr 5 0T5 /' L;le --IIII|ICH3 NaOCH2CH3 ‘h- H —" El ’ 1‘4. IIIICHB b. HBr (%H I 0 SN 1 BY) Br e. k t-butoxide [/f (-F +5, Dmo [31 OH TsCl —~———I- pyridine 0H 4. Consider the reactions in question 3 to answer the following questions. You can simply fill in the blanks with the letter of the reaction (a, b, etc.) A reaction that is regioselective is or A reaction that is stereoselective is % . 5. Draw a mechanism (electron pushing) of the following reaction. S m BrCHZCHgBr + NaSCHZCHZSNa —-——u—~—> . S J/ 3,41 3.. I it: [‘RD 6. .S/ 6. Draw the four isomeric alkyl bromides with molecular formula C4H9Br. /\/\%w /i\/ gr #9( E /\/ gr é. X 6 21. Which one undergoes E2 elimination at the fastest rate? Ans. l 2 b. Which one gives more than one product on E2 elimination? Ans. g 1 0. Which two isomers will only give the same product? Ans. E 'l/ l 2 7. Propose a mechanism (electron pushing) and an energy diagram for the reaction below. Include on the energy diagram all of the labels (axis, reactants)reagents, intermediates, transition states and products). Draw the structure of the transition states. TsOH 8. DeSIgn two d1fferent ways to make the followmg ether from an alkyl halide and alkoxide. Will one set of starting reagents produce a higher yield of the ether than the other? Briefly explain your answer. 0 \§ /[email protected] 5/ BY, 90 ‘ O 4” EC/K vk (Weds SL-waQl POM 0" K “ML 9. Circle the faster reaction in each of the following pairs of 8N2 reactions. a. @ 'CN + CH3CHzBr h bar-Lou- Cl CH3(‘3HCH3 + CH3O' m w c. I” Fix 0. + CH3CHzBr + CH3CH2BI I / d. CH3CH20CH2CH3 + HBr CH3CHzBr + NHZCH2CH3 less polar ' 1 CH CH Br + NH CH CH —___.. % (1119M? glide/Ml? z 2 2 2 3 solvent ...
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351 E3p key F09 - Chem 351 Name K E Nielson Practice Exam 3...

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