Final 2005 - Chemistry 213a 2005 Final Code 111 Page 1...

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Chemistry 213a 2005 Final Code 111 Page 1 Before you start, please enter code 111 on your Scantron sheet Questions 1 ± 3 refer to the structure of the antibiotic Penicillin G , shown in the box on the right. 1. Which functional group is NOT present in Penicillin G ? A) Carboxylic acid B) Thiol C) Aromatic ring D) -Lactam E) Amide 2. What is the hybridization of the indicated N and S atoms in Penicillin G ? N S A) sp 3 sp 2 B) sp 3 sp 3 C) sp 2 sp D) sp 2 sp 2 E) sp 2 sp 3 3. How many units of unsaturation are present in Penicillin G ? A) 10 B) 6 C) 9 D) 11 E) 7 O S H NH N O OH O
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Chemistry 213a 2005 Final Code 111 Page 2 4. Rank the following compounds from the lowest pK a to the highest pK a . OH 2 OH OH O NH 2 I II III IV Lowest pK a Highest pK a A) II I III IV B) IV I III II C) II I IV III D) III IV II I E) III IV I II 5. How many different tertiary alcohols are possible with a molecular formula C 6 H 14 O? A) One B) Two C) Three D) Five E) Four
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Chemistry 213a 2005 Final Code 111 Page 3 6. In the most stable conformation of the molecule shown below, how many substituents are in the axial position? O HO OH HO OH CH 2 OH A) 4 B) 2 C) 3 D) 1 E) 5 7. What is the relationship between the two structures shown below? CH 2 CH 3 H Br Br CH 3 H CH 3 H Br H CH 3 CH 2 Br A) They are both meso compounds B) They are different conformations of the same molecule C) They are enantiomers D) They are identical E) They are diastereomers
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Chemistry 213a 2005 Final Code 111 Page 4 8. How many different molecules are present in the five structures shown below? A) 2 B) 4 C) 5 D) 3 E) 1 9. Which one of the following alkenes is the most stable? A) B) C) D) E)
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Chemistry 213a 2005 Final Code 111 Page 5 10. Which one of these reactions gives the poorest yield of the product shown? A) + HCl Cl B) + OsO 4 OH HO C) + H 2 O OH H + D) OH + conc H 2 SO 4 E) + Br 2 Br Br 11. How many chiral carbons are present in the antibiotic Cefaclor ? A) 4 B) 8 C) 1 D) 2 E) 3 N S COOH Cl H N O NH 2 O
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Chemistry 213a 2005 Final Code 111 Page 6 12. How many total stereoisomers are possible for the compound shown below? A) 4 B) 2 C) 8 D) 16 E) 32 13. What is the configuration of each of the indicated carbons in the sugar fructose ? CH 2 OH O H HO OH H OH H CH 2 OH I II III I II III A) S S S B) R R S C) S R R D) S S R E) R S S OH
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Chemistry 213a 2005 Final Code 111 Page 7 14. Which one of A ± E is a diastereomer of the molecule shown below?
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Final 2005 - Chemistry 213a 2005 Final Code 111 Page 1...

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