Answer key to the practice problems

Answer key to the practice problems - PRACTICE PROBLEMS FOR...

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PRACTICE PROBLEMS FOR CHAPTER 10 AND 11 Chapter 10 1. Rank the following acids in increasing order of acidity AND Explain. S -H O -H OH S - O - O - resonance stabilized (weaker) conjugate base N P Br I O F S Cl Size 3 2 1 EN stronger acid 2. Provide the products of the following reactions. Indicate if the reactants or products are favored at equilibrium. OH + Na 2 CO 3 + NaOH + NaH Compound pKa 10 7.8 18 10.2 15.7 35 H 2 O OH SH OH OH HCO 3 - SH O - + H 2 O Na+ + NaHCO 3 S - O - O O - Na+ Na+ + H 2 O - Na + Na + pKa = 15.7 pKa = 10.2 pKa = 35 pKa = 10 pKa = 7.8 pKa = 18 H 2 smaller pKa product favored product favored product favored stronger acid stronger base stronger acid stronger acid stronger base stronger base
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3. Draw the mechanism for each of the reactions and give the major products for the reactions . Make sure to understand the concept and mechanism. O OCH 3 O OH HO OH H 3 C OH H H OH H H HO HO H CH 3 OH H 3 C O H NaBH 4 O OCH 3 LiAlH 4 H 2 O H 2 O LiAlH 4 NaBH 4 H 2 O H 2 O O OCH 3 HO O H O O O H MgBr CH 3 O Cl PhMgCl CH 3 MgBr O H 3 CO OH O O LiAlH 4 LiAlH 4 OH HO O H LiAlH 4 H 2 O H 2 O H 2 O NaBH 4 (mild) LiAlH 4 RMgX RLi R 2 CuLi (mild)
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Cl O i) Li Cl ii) CuI iii) Br Br i) Mg ii) CO 2 iii) HCl/H 2 O (work-up) Cl i) 2Li ii) CH 3 COCl iii) H 3 O + (work-up) i) Li Br ii) CuI iii) Br i) Mg ii) CH 3 O H Cu - Li + O CO 2 H O CH 3 H Chapter 11 1. Predict the major products of the following reactions . Make sure to understand the concept and mechanism for the reactions except for oxidation reactions.
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H 3 C CH 3 CH 3 OH Na 2 Cr 2 O 7 H 2 SO 4 OH O OH CrO 3 , H 2 SO 4 OH PCC CH 2 Cl 2 DMSO/(COCl) 2 (CH 3 CH 2 ) 3 N CH 2 Cl 2 H 2 O Swern O O O H O HO H 3 C CH 3 CH 3 O H H
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Answer key to the practice problems - PRACTICE PROBLEMS FOR...

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