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(CHEM111)[2009](f)final~kpleeaa^_10009.pdf
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CHEM111 FINAL EXAM (Fall 2009)

Name: (English) (Chinese)
Student ID No. . Note: This is a close-book examination. You are required to answer ALL questions. Please write answers on the exam. Maximum time is 180 min.
1. Give the R/S configuration of the chiral centers in the following compounds: (27 pts)
OH

2. Multiple choices. There is only one correct answer for each of the following questions, unless stated otherwise. (75 pts)
(1). The correct IUPAC name for the following molecule is: ( )
A. o-Mercaptophenol;
B. 2-Thiolphenol;
C. o-thiolphenol;
D. o-sulfyrylphenol;
E. o-hydroxy thiolphenol.
(2). The correct IUPAC name for the following molecule is: ( )
OH
A. 2-Hydroxycyclohexyl methyl ether;
B. 2-Methoxycyclohexan-1-ol;
C. 2-Hydroxycyclohexoylmethane
D. 2-Hydroxycyclohexyl methyl oxide;
E. None of above.


(3). The correct IUPAC name for the following molecule is: ( )
A. 1-Propylthiol
B. 1-Propanethiol
C. 1-Propyl sulfide; CH3CH2CH2SH
D. 1-Mercaptopropane;
E. 1-Thiolpropane.
(4). Which of following statement is correct about the molecule shown below: ( )
A. A meso compound;
B. Optically active because it contains chiral centers;
C. Optically inactive because it does not contain any chiral centers;
D. There is not a plane of symmetry for the structure;
E. It does not have stereoisomers.
HO HO



OH
(5) Yeast alcohol dehydrogenase catalyzes the reaction as shown below. Which prochiral hydrgoen at carbon-1 in ethanol is removed by the NAD+? ( )
A. pro-R hydrogen
OH
D
B. pro-S hydrogen
1 Alcohol dehydrogenase


C. si hydrogen
D. re hydrogen DH
NAD+ NADH
O
E. None of the above
(6) Yeast alcohol dehydrogenase also catalyzes the reverse reaction as shown in (5). In another word, it catalyzes a reaction as shown below. From which prochiral side of the carbon-1 in acetaldehyde does the hydride (:H-) from NADH attack? ( )
A. pro-R side
B. pro-S side
D
Alcohol dehydrogenase OH
C. si face
D. re face


O NADH NAD+ DH
E. None of the above
(7). Which of the following statement is correct about the outcome of the reaction below: ( )
A. Two diasteromers are formed;
O

HO CH3
B. A racemic mixture is formed;
1. CH3CH2MgBr
C. Achiral compounds are formed;

2. H3O+
D. Two enantiomers are formed;
H3C H
CH3
E. None of the above.


(8). Which of the following statement is correct about the reaction product (s): ( )
A. Two diasteromers are formed;
H2O
B. A racemic mixture is formed;

C. Achiral compounds are formed;

H3C Cl
D. The product is optically active;
H3C OH
S-3-chloro-3-methylhexane
E. The product is a pure R isomer.
(9) How many configurational stereoisomers does the following compound have ? ( )
A. 2
H3CCH CH

B. 4
C. 8
D. 16 HO
OH
E. 32
(10) Choose compounds with the highest and the lowest boiling point (b.p.) from the following list.