Chem210-1-2008-Exam3-Answers

Chem210-1-2008-Exam3-Answers - Chem 210-1 Mid-Term Exam 3...

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Unformatted text preview: Chem 210-1, November 24, 2008, Mid-Term Exam 3 NAME: fiflg WEIZS 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: H30+ IQCHZOH W O I n‘ + Q“ Cl—i—ZmHé?“H “WW-*9 Q35ivi-E {if-H22 ‘f- HE’S R ;’ sit-$3 mg; «4/— H- <—:-—~—- EDI kg 4.. .fm. ~i~ H30 [3. (10 points) Please present a detailed mechanism for the following reaction: 2. (20 points) Propose a reasonable synthesis of the foltowing molecule using acetylene, any other carbon compounds having no more than 3 carbon atoms, and any other reagents that you wish. (Remember, this is a synthesis probtem, not a mechanism problem.) 0% mic: EEC a «i: »— mat:er 03% T 0 Nil tilt: 2‘3) e:ng Haiti-2M fiflsmfia W H. ngtt fl HCzCMCHZCH-zmg a) agarth 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 products: 1 )03 C10H12 ——"' + + co CH 2 2)(CH3)2S H OH H3C 3 O O B. (10 points) Draw the structural formula of the alkene that reacts with KMnO4 under the conditions shown below to give the following product: COQH warm KMnO4 C13"{14 ——-—P concd CH2002H 4. (20 points) Predict the products of the following reactions. Make sure to specify the correct stereochemistry when necessary. if more than one stereoisomer can be formed in each reaction, show all of the isomers. (Each part is worth 4 points). A 2) Hay ©— {Haéiiafl‘ii 01-i- 1) LiA|D4 : QCHS —" CH’Z “'- C”{«H'3 CH3 2) H30+ i g 5 CH3 1) H/ELH _ CH3CHZCH2MgBr —> CHE (it: CH? CH“ 62% 3 Z 2’; Z 2)H30+ it :34 M {3+ Brz HC Q r’ \ C‘fi $26?le H30 H 3, M; (1’ mg + \ {i H x g” H it C i t \ 31 H CHZCHZCHg, 3 {5/2, aiizmzcrig H H 1) 8H3 —>- 5. (20 points) Please present a synthesis of the indicated molecule using carbon compounds that have no more than 3 carbon atoms and any other reagents that you wish. (Remember, present a synthesis, not a mechanism. Also, watch out for stereochemistry!) HOH CH3CH2 7 HO ‘74 CHZCHgCH3 W M (fizmgfflg aigcrlgtt mg mg sec; (:5!sz “E T f) Ma UH: 3) {fingéfiz e T D We? M453 a) CA; Ct‘é‘zgr #Cf—LCH ...
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