Wasielewski Exam 3 Key

Wasielewski Exam 3 Key - Chem 210-1, November 21, 2005,...

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Unformatted text preview: Chem 210-1, November 21, 2005, Mid-Term Exam 3 NAME: 560i $5 This exam has 100 total points with the point breakdown for each problem given below. 1. (20 points total) A. (15 points) Please present a detailed mechanism for the following reaction: BF2 0 M0” —- “Br H20 OH B. {5 points) Why doesn't this reaction give 3M0... as the product? A) Gun/B: ‘6 0H MD“ A J \/ ecA/O 6—- lac/€53“; .4— +H30 (1425+ 85 :5? eawgp) 2. (10 points) Show two ways (5 points each) to prepare 2-butanol in one steP using Grignard reagents. (Remember. this is a synthesis problem, not a mechanism problem.) OH arigllfaflfig : N O I) CHJCHZMgBI OH (1H ngH —-—‘e N 3 Z.3 H304- H. —H 2 3. (‘10 points total) A. (5 points) Draw the structural formula of the alkene that reacts with ozone under the conditions given below to give the following products: “03 C H O o O 0 1o 13 —'!I- + + 2) (was )K/ HJ-K/ILH W B‘ (5 points) Draw the structural formula of the alkene that reacts with KMnO4 under the conditions shown below to give the following product: 0 O warm KMnO4 03H1 4 —hr- H0 6 ’1 H concd. H H @Efi» 4. (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 wisn (Remember, present a synthesis, not a mechanism. Also, watch out for stereochemistry!) H OH CH CH -: 3 ‘é’CHZCHZCHa Ni/u H3 (£3 CR3 CH7: C 5 '1” films“: 7 O Na MHZ OH H) cHZc'Achg 5. (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 reacfion. Show all of the isomers. 0)} "- “cu “I. H‘ l n BHa ~“ 2+3 a“?! 6— 2) H202! NaOH H3 W 0F ENWIDMEKS ii Brz, H20 It; 31' \“ 3" ©— ——+ ‘00” 0H 1: on; ’6»; W Pam a? EmoTraw—zzs oii 1) Hg(OAc)2iH20 Que iSOH EL '3 2) NaBH4 w} 6. (20 points) Please present a synthesis of 3—hexanol using carbon compounds that have no more than 2 carbon atoms and any other reagents that you wish. (Remember, present a synthesis. not a mechanism.) 3— HESLpruoL “: W 0H 12 r) N a H “2, H20 1) an; c9134, HCECH ...
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Wasielewski Exam 3 Key - Chem 210-1, November 21, 2005,...

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