Chem210-1-2007-Exam3-Answers

Chem210-1-2007-Exam3-Answers - Chem 210-1 Mid-Term Exam 3...

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Unformatted text preview: Chem 210-1, November 28, 2007, Mid-Term Exam 3 NAME: flQSw Eb HINT: Some problems are easier than others. Please read the entire exam first. This exam has 100 total points with the point breakdown for each problem given below. 1. (20 points total) A. (10 points) Please present a detailed mechanism for the following reaction: cage CH3 Brz “\CHS U —"'_"‘ . r2 n+0 all-3 CH30H H IIBrC’f '4 pl c a at; 32/; ’Al 7 m CH3 gm ———> as W. Gen H H \L r 0130 t CH30‘H‘Z ‘u c H3311} t 34:) “ng CH 1‘ H H 9+8“ B. (10 points) Please present a detailed mechanism for the following reaction and give the products: ROOR, A [1013123 7 2120' RO- % (+81 —~—:—> RUH + 31‘ m} C” “i ll . rigs-Ma @[email protected]><:\fi%+31 (a. BL 1+ / W0 STE/€60 CHEM/cm; PfiEFE/ZEAJCEE 5f yaoggf :- 5 Inca.) “art; (1104. INCH- 4/ Alma/6’ g H H H 3 313 Z #4025 0/: H 4, 1 4/5?“ my Emma/Wis W J 2. (20 points) Propose a reasonable synthesis of the following molecule using acetylene, any other carbon compounds having no more than 2 carbon atoms, and any other reagents that you wish. (Remember, this is a synthesis problem, not a mechanism problem, so don't do any arrow pushing.) O '3 55a EH u 1 Ci _cacH CH “Cl-l: "(J'l " CH " C H QM“? CH5C(+Z +2 Z Z 7- '1) H2° T NQHHzJG DNa _ H H 2 H—C: Chcv crgc but 0 (H317 3 a 3 3. (20 points total) A. (10 points) Draw the structural formula of the alkene that reacts with ozone under the conditions given below to give the following product: (Hint: there are no three— membered rings in the starting compound.) 03 o\ /0 C7 H8 W (CH3)28 I I o o B. (5 points) Draw the structural formula of the alkene that reacts under the conditions shown below to give the following product: 0 OH H- H warm KMnO4 l l C10H16 WM '3- Concd. l; O OH C. (5 points) Draw the structural formula of the alkene that reacts under the conditions shown below to give the following product: it 0504 OH W C3on 16 L/ I H202 ‘"' OH II“ 4. (20 points) Predict the products of the following reactions. Make sure to assign the correct stereochemistry. If more than one stereoisomer can be formed in each reaction, show ali of the isomers. (Each part is worth 4 points). MgBr yo H30 cazcm C 1) lg Viz Haw 2) 1430* G H- I‘LBZN 1) LEAED4 ‘d: —"———————D' —H—i:——> >— CHZUH 2) H3O‘" + £1.36”; hL Br2 6’1 1% Bx ‘ WW 1”” 03’ 1) 3H3 (if? 0:} 2) H20210H— :’ 7:“H H H- H 7 5. (20 points) Piease present a synthesis of 1-phenyi~1~propanol starting from bromobenzene and bromoethane. You may use any other reagent that you wish. (Remember, this is a synthesis problem, not a mechanism problem, so don’t do any arrow pushing.) (Hint: you need an extra carbon atom.) Bromobenzene= 1—phenyi—1~propanoi = - OH OH 90 W D NaBHQrLLLMHq A / Q : + IQ} 23 H30 . (cgwgzauu h curl HO\C¢D Cf \ Loo i " 90”?“ A ce3u+ZLL 2) C02- CH'sC-H‘Zm r34 3) H3“ is; ...
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