Exam 3 Summer 2017 Name. ey Seat Number, Student ID, The exam consists of 8 questions worth 104 points on a total of 8 pages. It will be scored out of 100 points. The maximum score you may receive is 100 points. 1 sis ore. 3.20 eee 5. 6 Gos eats 8/4 bonus Total: Regrading: All requests for regrades must be submitted in writing within 48 hours of the return of the exam. You must explicitly state what has been misgraded and why itis an error. ‘The entire exam will be regraded, which could result in points being added or deducted overall.1. (16pts) Predict the ONE predominant mechanism (Sy1,Sy2, E1, or E2) for each of the following reactions. “ the mechanism you chose, draw the structures of the major product(s) in the box. Ee ‘A. | Type of mechanism: \ t | steer? 1 t ‘Type of mechanism: EQ -1 neyia/s fares C. | ype of mechanism: S/R ® | OH emg, oer AA — 7c aver! D. | Type of mechanism: FQ } ae of oO 080,CH, (CH);CO" —(20pis) Predict the major product(s) of S of the following 6 reactions. Be sure to include proper stereochemistry. Put an “X” in the box you do not want graded, or else the first 5 will be graded. (S}-2-butanol PBr, 1, CH,$0,Cl, py 2.HS 1. Mg. ether 2 “So 3.30" HBr 1804, heat excess Jones reagent (ehromic acid) OH ~t stereo | ~1 reg. F-| stece? cal allehy de3. @Opts) Provide the reagents or starting materials necessary for 5 of the following 6 reactions. Putan *X” in the box you do not want graded, or else the first § will be graded +4 Abily , CHoH ] oS LAH ‘OH 1. CHjCHMgCl Ad &) other Ketone 2. HO" We of ahehyde & “oH oH Pee ; 2 Seue $ NZ HOCH , HY 7 Ei) no ed + 3) GHcR ce Ho yen v 4) He Le BMS MyBe 7 yor ke op OY 3 ae y PB, skep on 8) 5, ee ‘OH ) Pv \ gb PBr, Py 40° FOL = Ma qh Be enet ore >) Hor cakerrnediet = 4 Va neon ree ) PAMASe on Paty NF » MDEE 3) Tons or Pee i) Phtyee | 4) cy Mg Be ayer Y ) H.o® Aq Me Sense : As, My Be purely Hor ye 2) 430 On6. (pts) Four possible products of this epoxide ring opening are given below. Underneath each product, explain whether it will form as a major product or a minor product, or if it will not form at all due to regioselectivity and/or stereospecificity of the mechanism. 1. CH3S" 2. acid quench ——_—_> Not Formed becavee | Mey ec - attack Tren | Nui” amusk wack From boot ne ( stetospe = F back Fox 2 a wad of |e55 hadersd corban * Gees 2 Coegrogelevtwe) oH Not Formed because Nair musk ofc From back Face, (sleeaspeehs) Monoe ~ attack 15 From | boek Face ( stereospen fe) bubs on more hndeded | S.de Creq.a seketwe)7. | Provide an arrow mechanism for this reaction, including all intermediates. ne 206 © au z ATO © Ma st me Cit Ce ) ART Ke 1 & Ceererage’ A2) resononc® 8. (4pts bonus) Which of the following reactions that form cyclic ethers would be fastest, and which is slowest? Explain, © NaH 1} @ Fastest ~ enteopy acgument ae = JB) ® Slowest ~ Stain angument