Name: — ey __ ID#: Signature: Chem 350 Fall 2016 Exam 3 There are 9 pages in this exam and a periodic table You have 90 minutes to complete this exam You may use a calculator and/or model kits on this exam You may write on the back of the pages, but any material there WILL NOT be graded In addition to putting your name on the front of the page, put your name on the back by the staple * Be legible; if | cannot read your answer, it is wrong * 140 points total (for this exam) Multiple Choice (60 pts.) Page 7 (21 pts.) Page 8 (22 pts.) Page 9 (47 pts.) Free response total (90 pts.) Chem350 - Exam 3 11) Assign the following alkene as E/Z BA aE b Z An a Assign the following alkene as E/Z ae B b.Z An 8 ok 3) Assign the following alkene as E/Z A aE b.Z He 4) Assign the following alkene as E/Z 3 ae OCHS bz mo, 5) Rank the following carbocations in increasing stability (least stable to most stable) a teili > Use the following reaction to answer questions 8- 9 OH | OH _HSO4 Cte oooh 8) Which product would have the highest energy transition state leading to the first intermediate? a. lonly b. Ilonly c. Illonly d. and Ill only e. land Ill only 9) Which product would have the greatest amount of hyperconjugation stabilizing the carbocation intermediate? a. lonly b. llonly a c. Mlonly 5a > Nad. Land Ill only a e. Hand Ill only sen 10)Which of the following energy diagrams represents thé acid catalyzed hydration of 4- methylpent-2-ene with suffuric acid, water, and heat to make 2-methylpentan-2-ol? ? i 3 3] Exo Endo Taio ease Tenants emtantsanpnas—— Weason tera Sorte A B Cc te B & 11)How many different alkenes could give rise to 1-iodo-1-methylcyclopentane in high yield upon treatment with HI, assuming only one C=C is present in the starting material? : 1S OT aS ae x BONA b. c. d. e. Chem350 - Exam 3 3