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Name: Mey ID#: Signature Chem 350 Fall 2016 Exam 2 ‘There are 8 pages a pKa table and a periodic table in this exam the staple Multiple Choice Page 6 Page 7 Page 8 Free response total You have 90 minutes to complete this exam You may use a scientific 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 Be legible; if | cannot read your answer, it is wrong * 140 points total Substituent Avyalue (kcavmo} oy CN 0.20 (# pts.) F 0.24 C=C oat I 0.45 a 0.53 (18 pts.) Br 0.87 OH 0.93 NHe 1.41 (@ pts.) COM 1at C=C 170 CH; 1.76 48 pts. CH.CHs 4.75 (sels) CH(CHs)o “iPr” 2.15 Ph 3.0 4 C(CH)s tBu" 5.0 Oo & pts.) a lalp = IamxcZ) (am)xc(3) @)pobserved eee = [elo [a]p pure sample ‘Chem350 — Exam 2 1 1) BL 2) E Which of the following is/are identical of the boxed structure? tonly a b. Ilonly ve N(CHg)o CH,CHs c. Land Ilonly iH Hy d. land Ill only CHACHs HN Nou cH, HN® N(CHsl2 e. Hand Ill only 1 Ww au Rank the following in order of increasing acidity (least acidic to most acidic) \ig. Weivclticl b We en # MWeilel Use the following energy diagrams to answer questions 3 to 5, assume all are drawn to scale 3) 4) 6) reactor Teacton Teacton Teacion conrdinate cooranste coordinate courdinats Which one(s) represent(s) exothermic reactions? tonly 2only 1 and 2 only 3 and 4 only 1,2, and 3 only ese Which one represents a reaction that is possibly too slow to occur even though it has a negative AG°? a. tonly b. 2only c. Sonly led. 4 only e. 2and3 only Which one is the fastest reaction? tonly 2only only 4only 2and 3 only eaocn Given the following chair cyclohexane conformations, which one is more stable? a. Ais more stable cl iPr b. Bis more stable ipr ol c. They are equal in energy NC: ie iPr i ‘oH by oN A 8 ‘Chem350 — Exam 2 7) 9) B 11) Ita sample is place could notbe a reason? The sample is achiral There is more (A) enantiomer than (S) in the solution The instrument is not plugged in There is a racemic mixture The sample is a meso compound a polarimeter and no light rotation is observed, which of the following gaegp Rank the following in order of increasing acidity (least acidic to most acidic) d. l

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