WS2-W08 - Cl Me NaNH 2 b Mechanism Chem 51B Jarvo c OH H 2...

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Chem 51B - Jarvo Worksheet 2 1. Assign the following alkenes as monosubstituted, disubstituted, trisubstituted, tetrasubstituted, and/or terminal. Assign each alkene as E , Z or neither. CH 3 CH 3 CH 3 CH 3 Ph H Et CH 3 Br CH 3 CH 3 H 3 C O CH 3 2. Consider the addition of HBr to the following alkene: CH 3 Br HBr ! G = -20 kcal/mol + A B Br Draw a mechanism for the reaction. You should have one pathway that provides product A and second pathway that provides product B . Will A or B be the major product and why? 3. Draw the products you would expect from the reaction. Label the major product and the minor product. Label the mechanism you would expect (S N 1, S N 2, E1, E2) and provide an arrow-pushing mechanism for the reaction. a. I CH 3 H 3 C CH 3 H H 3 C HOCH 3 Mechanism:
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Unformatted text preview: Cl Me NaNH 2 b. Mechanism? Chem 51B - Jarvo c. OH H 2 SO 4 , H 2 O CH 3 Absolute configuration: 4. Fill in the boxes with the appropriate starting material, reagent or major product. Show stereochemistry where appropriate. Br 2 , CH 3 HBr Cl 2 , H 2 O CH 3 CH 3 Ph H Et CH 3 Absolute configuration: HCl H 2 SO 4 , EtOH CH 3 Chem 51B - Jarvo HCl H 3 C CH 3 Ph Br 2 OCH 3 + OCH 3 CH 3 Cl Cl + Cl Cl Cl 3. Ranking: a) Fastest to slowest reaction with NaNH 2 : H 3 C H 3 C CH 3 H 3 C A B C CH 3 Br CH 3 Br CH 3 Br b) Place the acids on the pK a scale in order from lowest to highest pK a . O H 3 C OH H 2 O NH 3 HCl OH H 3 O A B C D E F lowest pK a highest pK a-10 10 30 40 20...
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WS2-W08 - Cl Me NaNH 2 b Mechanism Chem 51B Jarvo c OH H 2...

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