Midterm_2_M10_Key

Midterm_2_M10_Key - Name HfijtPFWTIS Page 1/20 Page 2/21...

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Unformatted text preview: Name HfijtPFWTIS Page 1 ______/20 Page 2 _____/21 Page 3 ______/17 Page 4 ___./Z4 Page 5.....__/12 Page 6______/8 Total _..__/100 Perm # a. Can one predict whether a compound with a singie asymmetric center is dextro- or ievorotatory based on the R/S assignment at this asymmetric center? Explain briefly. (4) Mo #16 finger/ricer R or S AefeMs om / . 65N-1W wwwae runes wk \Mg Wm \Depurwxf) ovx "We (MFG—"Hem 0“? were“ as? imam Pom: 1212K \ifik‘r. b. Because enantiomers have the same physical prope‘réies, how cg) chemists separate them from each other? (-4)fir 9A3 “a“ . _ Us} 6" LLou rs ng+eu r) (D Reéom’him on; (meme. Misha ® 921'“: H‘ZAMSA @ Chrom‘x‘ojmvxuj vhf-Hr" a. C,\/\{M\ Probe. (SQUA Phage) 2. Consider the one step conversion from compound A to compound B. Given that the reaction is endergonic by S kcal/mol and that AG¢ is 20 kcal/moi, draw a labeled reaction coordinate diagram keeping the sketch is consistent with the energy values given. (6) W l Ema” . Rm {9551” 635 "7-3 . 3. Based on the followmg energy dragram, explain in terms of thermodynamics and kinetics which compound, A or C, is formed faster from 8? Which is more stabie, Aor C? (6) A 1“) HM: ktnefil‘c roaxoLV LWX i9 ,, if 4r h‘ a. Jamar ‘QNQHZK, Jn +19 Case] e be. A 3 iodwct {9 mt 'We Wermo (Marv/time C induct“ C is More Shlole [06010342 {1% Reactioncgcrdinatew 1.5 [Owar [A char/5 firm A: A M, fi .1 gbfW‘Qlk £m9d‘6( LECVNW EEC“: 343A lg, \owef ’HANA DEE; 8””? C. a 4. In the schemes below, fill in the missing reagents or major product. (15) i 2 No 9%“ (114202 Rag/Will Umg;‘l6\\0\fi, " -. OCH; cl (:12 MeOI—I / ' ‘ (Dang/THE @ ”3% i Mall, Mao HO 5. Name the following compounds (6) 6. Which of the following terms best describes the pairs of compounds shown below? Enantiorners, diastereomers, or the same. (6) emw’d «a w rs 50mm, was +efeol/Mers. 7. Label the following addition reactions as anti, syn or neither (8) a. Bromination of an aikene with Bra: Aver; b. Electrophiléc addition of HBr to an alkene: Menu/«2. f” c. Peroxyacid addition to alkene: éaw d. Hydroboration oxidation of alkene: $3“ 8. Which compound has the greater electron density on nétrogen? Explain (3) ehdtraws one [:3 I“ e\e<:lm€ one &e,\oca\izerk l l lemma , m f-QSorlnl/Lce ‘gw m9, 9. Draw the products of the following reactions to include the proper stereochemistry. If two or more stereoisomers are made, then state their retationship (enantiomer, diastereomer, or meso) (24) 8 r2 M magma LBHs/THF WW 2. N30”, 8202, H20 3' B HCE m WWW-W '— \ Na, was (E) 18°C \.:\__. H2, Pt 10.Which is the correct order of decreasing acidity in the foilowing compounds? Number them: 1 being most acidic (2) _H2o..CH3nCH3 NH3 CH2:CH2 HCECH I g 3 “i 9x 11.Which of the foiliowing is the stronger acid? Explain using resonance structures to prove your answer (4) “this Nag Wart; (‘65:)anth germs encounter in reaching this product? (6) i ii 3’06 H I. 2“ H ”2804 (33:), H20 H30 + [10501 ~42; rise“ new El 1 k J. “W r w; B V») C \ tlk .I e .53 all}! M I S f. $ ‘ m w m a e m wsmm m my: wwwwfiu W .E mmwm G. mem e \JE m Wmmm S xIL C 1...; m $4: $9 $0.. imamwfi e mm ”W/ n.1, Mm n c: V ,w w b ms 5 MN ‘3 am .ru .T 5mm % .1. ,1 .m mm... .wm “an OD» rnu mmfim o 3 0 gnefi In M ii: Wynn.“ 3 “H v F WMMW m H N C _ H% htmemfl t www.mfi 8 @® : w __ v \Isw , O . ‘ VII 0.. 3 1 ...
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