Exam_3-Chem35-2006-key

Exam_3-Chem35-2006-key - Name SISD Chemistry 35 Exam 3...

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Name____________________________ SISD________________________ 1 Chemistry 35 Exam 3 April 26, 2006 Print your name and SISD number on EVERY PAGE of the exam. Write all answers on the exam. There are two blank pages at the end of the exam for you to use as scratch paper. 1. (18 points)__________ 2. (7 points)__________ 3. (10 points)__________ 4. (15 points)__________ 5. (12 points)__________ 6. (18points)__________ 7. (20 points)__________ Total (100 points)_________________
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Name____________________________ SISD________________________ 2 1) (18 points) For reactions (a) - (g) (this page and top of next), provide one of three responses in the box: OK if the reaction is correct as written NoReaction if the indicated reaction is wrong and NO REACTION WILL OCCUR Provide the structure of the correct product . if the indicated product is incorrect. Cross out the incorrect structure I OH H O O CH 3 CCC H 3 KCN CN CH 3 OH O H OH O H O H K O CC KI K MgBr H OH O CH 3 H Li (a) + + a (b) + Li + CH 3 Li b (c) + CH 3 MgBr c (d) + NaBH 4 d (e) + KH e + CH 4 O 1 mole 1 mole 1 mole 2 moles 2 pts - no reaction No Sn2 at sp 2 2 pts - no reaction 2 pts - OK H 3 C is a very strong base H transfer from alcohol is fast and exothermic 4 pts 2 pts reduce keytone 2 pts reduce aldehyde CH 3 H OH H OH H 4 pts 2 pts alkoxide (deprotonation) 2 pts no rxn at aldehyde O H O K KH is a strong base but not a reducing agent
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Name____________________________ SISD________________________ 3 Br O H S O O H 3 C Na OH SCH 3 H SCH 3 (f) + CH 3 S f (g) + H 2 O 100 0 C g 2 pts 1 pt substitution 1 pt inversion 2 pts - OK 1 pt if cross out product and write: 2 . (7 points) Consider the following nucleophilic addition reactions to 2-propanone. Cl O O NC O Me C C CO C Me NC O Cl O K F K CN K CC + + + (a) (2 points) Rank the three equilibrium constants from LARGEST (most product) to SMALLEST. 1 pt 1 pt K CC > K CN > K F (K Cl ) (b) (5 points) Explain your equilibrium constant ranking. Remember, equilibrium constant is a thermodynamic quantity.
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Exam_3-Chem35-2006-key - Name SISD Chemistry 35 Exam 3...

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