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322bsu09_e2_key

322bsu09_e2_key - Chemistry 322bL Name Bfili ‘ JMQM 003...

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Unformatted text preview: \ Chemistry 322bL Name Bfili ‘ JMQM 003:) Basic Organic Chemistry July 20, 2009 TA pufT/M' EXAMINATION 2 Q Answer the following questions in the space provided. Please organize your thou ts attempt to make your answer as legible as possible. If we cannot read your answer, it com e en credit. Please remember that C-C-C-C without hydrogens and “stick” structural representations will be given N 0 credit (except for rings only). 1 (14) 11 (befi‘l l III (18) IV (27) v (16) V1 (20) TOTAL (193) Read each question carefully in its entirety. Check immediately for 8 (including this cover) difi‘crent, non-blank pages in this document. Chemistry 322bL Examination 2 page 2 July 20, 2009 I. ( I lists) Provide names for the following structures, or structures for the following names, as appropriate. Either IUPAC or common names are sewn Be sure to specify stereochemistry if 1t is shown. (a) 0 H if“ ()L ”6 flay] 6722(0'3 hex“! ”1‘01 A (I: (Q7 0 We 1': “H E; - g $3~ ‘3— hadmxa» fl - Pkg/VL- é hgxzfl - j .. DMZ (b) 0 <3? WW3 Mata {qr rmgagggg’toehemne Wt ~ (d) o-nitrostyrene (e) 4-chlorocyclohex-3-enecarbaldehyde \/CJ“:C—Hz <2) (3) 43:6 “‘ II. (C’pts) (a) Complete the following partial structures so as to draw all reasonable resonance structures to complete a good representation for the indicated carbocation. There may be more partial structures than you need. Chemistry 322bL Examination 2 page 3 July 20, 2009 III. (18 pts) Please fill in the blanks or the best answer for each of the following. (a) Number the following molecules in order of increasing boiling point (1 is lowest, 4 is highest). 0 OH CH 3 o 8 CH CH \cri (H CH3 \CH3 CH3 CH3 CH3 CH3 H2 CH3 4%.; (b) Circle the set(s) of conditions that does(do) NOT reduce a ketone to a methylene (- -CH2-) group? 1) LiAlH4, EtzO in pyridine 3) LiAlH4, Etzoll Chemistry 322bL Examination 2 page 4 July 20, 2009 (i) Which of the following undergoes solvolysis most rapidly in acetic acid? (g) Which one of the following is least likely to yield one dominant regioisomer on electrophilic nitration? Br 9 N02 <1> groom ©CN CHSOQCFa CI\©\CH3 \. IV. (29pm) Give the organic products for the following reactions. More than one step may be required for a given compound. Be sure to note product stereochemistry and/or regiochemistry if the question explicitly shows it. You do NOT need to balance the equation, show byproducts, or show any mechanism. (Note that "No Reaction" is always a possible answer.) (a) o H / 3 \ at 8 9 . \CH; \H 0310wa add /\ CHICHJQH CO H \M/ 9C}; + KCN 1equiv. HCI Vi, 2 W E 1equlv. 2) conc HCITl OCH? CO": I) 7" CYM‘VQ (b) C”) ”1 CH 3 \ ‘O/CkcHzcl-la + NHZOH :3; Q ‘\\N—OH (c) GHQ-69 + ago /\‘ 042.04 = CH ~ C 0, Et \H Ph3P=Cl+COZEt A\ [j (2) H20 new ”of W Chemistry 322bL Examination 2 page 5 July 20, 2009 (”mac (1) Na in CH 1 Q NH3(uq), EtOH 5R/\ m CH, (2) H20 workup U0) l (t) {D + EEN'B' peroxides {\U/R 6% o . CCl4fl 0 CH3 (g) C'ja [CH3 /_< C”; g /6 CH <3 (1)H—Al C/ <jCW3 ¥< ‘ ‘H hexane, -78 °C H C . CH3 (2) H20 W 0 (h) (3 )5 0 I604 (1 t2 C\CHa . —78 °c &\‘/ / 3 -. Cl + L|[AIH(OtBu)3] \ '"fi/ (2) H20 mu Ca‘.‘ 0 W72 /' ’8, (i) C C'H3 AICI3 \// [CH '5 + CH3 —(|3 -CHz -Cl A x ( CH3 CH; 1 CH3 CH—C-CHICHB Chemistry 322“. Examination 2 page 6 July 20, 2009 V. (16 pts) Provide a reasonable synthesis (l.e., minimum number of steps, good yields, good stereoselectivity, good regiochemistry, etc.) for the molecules specified below from the indicated starting materials and any other needed organic or inorganic reagents. Be as specific as you can regarding reagents and conditions. Show the product formed fi'om each important step of your synthesis. Be sure to indicate if a step results in formation of an ortho-para isomer mixture, but assume that such mixtures are readily separated. ‘ a C02H goeH O H U c: 471’” HMO; ‘ c; E) """" Kori} sin/k” ”2904 Q _. .« 3% + O‘HCl A <3? (”:50 6’0 @‘ ”oz (D iw’mnM A03)A q” NaDH CH C '5 i420 “43 on . 3 ”3 u j C‘ A 65 ———-->-2 </\ + (if ——E“——>$“ "m U (29 Haw FaClg ‘ A Cl 0 l Cl <01: 0 + O ---------------- 4— OH c’CIiz C'ib <- Chemistry 322hL Examination 2 page 7 July 20, 2009 VI. (20 pts) (a) Provide a detailed mechanism for the following transformation which is believed to involve specific acid catalysis. There are six (6) generally accepted intermediates in this reaction, so only six will be graded. Also, show in each box the arrows appropriate to rationalize the next step. The quality of the electron pushing will contribute to the grade. O‘IK’_~~ /__\ H Hg}: OH 0 ‘ L] I l + H20 catalytic st04 6 (w) Chemistry 322bL Examination 2 page 8 July 20, 2009 accepted intermediates in this reaction (including both the ketone and the methyl-ammonium salt), so only four will be graded. Show in each box the species needed for the next step and arrows appropriate to rationalize the next step. Also, if general acid catalysis is involved in a specific step, check the box next to the equilibrium arrows for that step. The quality of the electron pushing will contribute to the grade. .. ...
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