david8A-FinalFALL09

david8A-FinalFALL09 - Name Last First(PLEASE PRINT...

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Name:______________________________ Last, First (PLEASE PRINT) 1 CHEMISTRY 8A FALL 2009 Final Exam December 7, 2009 Professor S. S. David 1. (12 points) 2. (18 points) 3. (24 points) 4. (12 points) 5. (10 points) 6. (8 points) 7. (10 points) 8. (10 points) 9. (24 points) 10. (24 points) 11. (16 points) 12, (10 points) 13. ( 8 points) 14. (6 points) 15. ( 8 points) Total (200 points) Extra Credit (10 points)
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Name:______________________________ Last, First (PLEASE PRINT) 2 1. Appetizers (2 pts each/12 total). Place answer in box i. Which ranking of the leaving groups is correct? a) OH - > H 2 O > F - > I - b) H 2 O > F - > I - > OH - c) I - > H 2 O > F - > OH - d) F - > I - > H 2 O > OH - ii. Mechanistically, the Williamson ether synthesis outlined below is: OH O 1. Na 2. CH 3 I CH 3 a) an E1 process b) an S N 1 process c) an E2 process d) an S N 2 process iii. Looking at the pair of stereoisomers below, determine if they are : CH 2 OH H 3 C H HO H OH CH 2 OH H 3 C HO H OH H a) enantiomers b) diastereomers c) identical iv. Which of the following chair conformations is the most stable? Br Br Br Br A B a) Compound A b) Compound B v. An acid with a low pK a : a) is a weak acid. b) is a strong acid. c) has a weak conjugate base. d) both b and c. vi. Which of the following has the greatest solubility in pentane? a) CH 3 OH b) CH 3 ONa c) CH 2 NH 2 d) CH 3 OCH 3 e) (CH 3 ) 3 CH
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Name:______________________________ Last, First (PLEASE PRINT) 3 H 3 C CH 3 O H H 2. Finger Food (3 each/18 total) . Place letter corresponding to answer in box at the right: i. In the following reaction, which product predominates?: a b ii. What types of intermolecular interaction does (CH 3 CH 2 ) 2 NH undergo? a) dipole-induced dipole (Van der Waals) b) dipole-dipole c) hydrogen-bonding d) a and b e) a, b and c iii. What is the appropriate formal charge for the following molecule? a) +1 b) –1 c) 0 d) +2 e) –2 iv . Which of the following compounds has the highest boiling point? H 3 C CH 3 H 3 C H 3 C CH 3 CH 3 H 3 C CH 3 a b c v . Which of the following alkyl halides is the most reactive in an S N 1 reaction? H 3 C I H 3 C H 3 C Br CH 3 CH 3 CH 3 I a b c vi. What pair of reagents (d, e, or f) would give a successful synthesis of (CH 3 ) 3 COCH 2 CH 3 ? a. (CH 3 ) 3 CO + BrCH 2 CH 3 d. a and c b. (CH 3 ) 3 CBr + OCH 2 CH 3 e. b and c c. (CH 3 ) 3 CBr + HOCH 2 CH 3 f. a and b
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Name:______________________________ Last, First (PLEASE PRINT) 4 3. Potpourri (24 pts) i. (8 pts) In the structures of progesterone and norlutin below, circle all stereogenic (chiral) centers.
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david8A-FinalFALL09 - Name Last First(PLEASE PRINT...

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