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Sample Final Answers - Sample final type questions CHM2120A...

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Sample final type questions CHM2120A 1. Show the mechanism for this reaction and explain which side the equilibrium lies on. O + HO O H O + O O H pKa = 8 pKa = 22 more stable conjugate base - acid has a lower pKa eq favors this side 2. Rank these electrophiles in order of increasing reactivity toward hydroxide ions. Br O S CH 3 O O I Cl O O 2 N 1 two en atoms make the carbon very electrophilic, no backbonding from chlorine 2 3 4 allylic system plus great LG, primary carbon has very little steric hinderance iodine is a good leaving group but secondary alcohol adds steric hinderance alkene are poor electrophile because they are very stable functional groups 3. Rank these aromatic compounds from least reactive to most reactive with SO 3 , H 2 SO 4 and show what the products will be. S S O O Cl OMe OMe least reactive 1 strong EWG most reactive 2 strong EDG, 1 weak EWG 2nd most reactive 1 strong EDG 3rd most reactive S O O SO 3 H S SO 3 H SO 3 H Cl OMe OMe SO 3 H
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