Chemistry Exam

Jul 11th, 2016
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Chemistry Exam

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Chem 234: Exam #1February 9, 2015Name:Student ID number:Discussion TA:Discussion day and time:Seat Number:(1) Put your final answer in the box, when provided, to obtain full credit.(2) Please turn off any electronic devices.(3) People caught using electronic devices will have their exams confiscated.GOOD LUCK!Point total:Question 1 (30 pts):Question 2 (30 pts):Question 3 (15 pts):Question 4 (35 pts):Question 5 (15 pts):TOTAL POINTS:Out of 125 pts1.(30 points) Predict the products and indicate the relative stereochemistry for thefollowing transformations. When necessary indicate the major product.(a) (5 points)1. MeSNaPhMe , DMFO2. H 3O+(b) (5 points)1. LiAlH 4, Et 2O2. H 3O+OOEtMeMe3. DMSOOClClOEt 3N, CH2Cl278 22 C(c) (5 points)Me MexylenesOMeheat3(d) (5 points)Me1. h, n-hexanes2. HBr, 0 CMe(e) (5 points)1.MgBr, Et 2OOH2.H 3O+3. PCC, CH2Cl24.MeMexylenes, heat(f) (5 points)MeMeO1. NaBH 4, MeOH2. PBr 3, pyridine3. Mg(0), Et 2O4.Me MeOH5. H 3O+42.(30 points) Provide the necessary reagents to accomplish the desired organicreactions. Please number the steps and note that some reactions will require morethan one step.(a) (6 points)OEtOMeHOMeOEtOO(b) (6 points)OiPrEtSO5iPr(c) (6 points)MeMeMeMeCO2MeMe(d) (6 points)MePhMeMeHMeMeOH6Me(e) (6 points)MeMeMeMe7OH3.(1

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