2011 Exam 3 Answer Key

2011 Exam 3 Answer Key - Name Ajfibfier Kg BannerID Box...

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Unformatted text preview: Name Ajfibfier Kg} BannerID Box # 1. [21] Provide the reagent(s) necessary for carrying out the following transformations. Some of these may require more than one step. Naome 9” Mm“ \ MO‘T NQO-‘HBBM 0/\/ Br at SQ\C§~QJ” m%% G) or'LD 9-! mflfize‘rt ~ § Wadi-QB) M e @ee Cg / C3,} B Neg Q‘tmg vx Q) r 0:303 —-—————-—————> 3.533% [+“quQH I} first (ififib‘m‘ ac‘i‘; gayffih 9"“ “33%) \> $(‘31H2Q a, :23 Matt @F%Rl on g) (8‘ F ‘tfixfifim + enantiomer 0H , @D \A N u%\¥_‘ + enantiomer gm Gram 2) Law 3 Name BannerID Box # 1. continued \5 "EU $3er D D OH 9 P939) («605;sz D Cl O‘—\( @ 011% o 4" 0 CI_ a on. 1} I 1%; Name BannerID Box # 2) [12] Compound A has the molecular formula Cng. 03: the“ M923 B excess A920, H2O ——-————> CsHs C5H302 C5I-1803 Reaction #1: Ozonolysis of A followed by treatment with dimethyl sulfide provides compound B, C5H302. a Draw all of the ossible structures of A that are consistent with Reaction #1. __ Reaction #2: Treatment of B with silver(l) oxide provides compound B, C5H303. b) Draw a circle around all of your structures for A that are consistent with Reaction #2. Reaction #3: Treatment of A with H2 Pd/C provides two diastereomeric products. c) Provide a structure of A that is consistent with all three reactions. d) Identify Reactions 1, 2, and 3 as a reduction, oxidation, or neither. 0 Reaction #1 C9 ‘24; ~ Reaction #2 O KR - ’3 Reaction Name BannerID Box # 3) [10] A retrosynthesis, which is the reverse of a normal synthesis, starts with the product and works backwards to a starting material using known transformation. For example, a retrosynthesis of acetone (shown below) might indicate that it can be obtained from isopropyl alcohol, which in turn can be obtained from propene. 0 OH :2) :2) A sample ren'osynthesis of acetone Use retrosynthetic arrows to show how the acid D can be made from the alcohol E — i.e. Show the immediate precursor of D; then show its immediate precursor, and so on until to get to E. You do not need to show reagents, but any retrosynthetic step that does not have a corresponding reagent that carries out the transformation in the forward synthetic direction will not receive credit. Name BannerID Box # 4) [16 pts] Provide a detailed mechanism for the following reactions. Your mechanism must: 1) Show the individual chemical steps and all intermediates formed in the process of converting reactant to product; 2) Correctly use curved arrows to show changes of bonding and lone pair electrons; 3) Show all formal charges; 4) Employ only the starting material and reagents listed. 31) R . C : g / :B—H if N / / Nélg W R R/B\R + N¢ F N Lg: Lag/j N (23> E”? E: “r W as»; we _ sf? 3 mg la ’9‘?“ N gt w 6 I” N Draw a contributing resonance structure for F. Name BannerID Box # b) 4 continued, see previous page for instructions. 0 Q flfi \xfio/ i Cf; 7 F30 OH O / ——~———> CH CF D Ph 2 2 Ph D (9 \XVNO (I) DO \ O 9 )%F3 (0 V“ e9 4 0 .‘g d \\ ’i a D Q :9 DRAW A BOX AROUND AN INTERMEDIATE THAT HAS MORE THAN ONE CONTRIBUTING RESONANCE STRUCTURE. Name BannerID Box # 5) [10]. For each of the reactions shown beiow, write correct in the box if the starting materials can be converted to the products using the reagents given. If the reagents are not correct, provide in the box a new set of reagents that can covert the starting material to the product in three synthetic steps or less. If the starting materials cannot be converted to product in three steps or less, write not fixable in the box. \/\\ We“ NaOtBu ltBuOH \ 9 Br Na® 1)Br2/H20 o _ , / \ 2) NaH O ——> ' O i) Dzsramyl borane Ph 2) H202 Ph Name BannerID Box # 6) [22] Synthesis Problems: Propose a series of reactions (reagents and conditions, if necessary) that convert the Starting Material into the Final Product. You can add any other molecules to your reactions, as long as some or all of the carbon atoms in the starting material are present in the final product. To get credit, your starting material and product must contain the stereocenters exactly as specified in the problem. You do NOT need to draw mechanisms for each reaction. Structure your answer as follows: etc Starting Reagents-1 ProducH Reagents-2 Product2 ' Final Product . —-——-——————————> . MaternaKs) (Wllh correct stereochemistry) 10 Name 6) continued BannerID a 11 Box # Name 6) continued BannerID Box# 0: CI T —’ WM NODJYQ)» \/ 29% éf WNW; » 1%“ "2% - DR 9“ onfino >4 0“,— aLFSS‘Vak \/ vow/:2) \Q [10 j W3 \1 0% 500% )4 PE‘" '15 26290 '\ 12 Name BannerID Box # 6) continued 61> CN 13 Name BannerID 6) continued HsC—CEC—H 0&1 Am“ /\\1/L:55\w b) WK, a A? WWW 9w mif- 14 Box # Name BannerID Box # 7) [10] Propose a synthesis of the molecule shown below usng acetylene as the only source of every carbon atom. (You can use acetylene as many times as you need to.) _ = __ —-——> H C—‘C H “"“" A EtO OH 15 ...
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2011 Exam 3 Answer Key - Name Ajfibfier Kg BannerID Box...

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