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Second Review Exam -- Organic Chemistry, CHEM 2210 -- November 2000 -- A
- What are the reagents and conditions necessary to complete the following reaction?
CH 3 CH 3
CH 3 CH 2 Br + HBr
A. Zn, HBr B. Br 2 , Ni (catalyst) C. Br 2 , light D. Br–, light
- Which of these choices correctly describes the positions of the isopropyl and hydroxyl groups in the most stable conformation of cis -4-isopropylcyclohexanol:
A. isopropyl equatorial, OH equatorial B. isopropyl axial, OH axial C. isopropyl equatorial, OH axial D. isopropyl axial, OH equatorial
- Which of the following alkanes has the lowest boiling point?
A. B. C. D.
- Which of the following statements is NOT true?
A. Any molecule with a stereocenter must have a stereoisomer. B. Every meso compound is achiral. C. Any molecule containing tetrahedral stereocenters must be chiral. D. Every chiral compound has an enantiomer.
- What is the percentage of R enantiomer in a sample that has the enantiomeric excess (optical purity) of 60% of the S enantiomer?
A. 20% B. 30% C. 40% D. 60%
- What is the relationship between the following structures?
H 3 C
H
H
OH OH
H
CH 3
CH 3
H HO
H 3 C
OH
A. Same compound B. Enantiomers C. Diastereomers D. Structural isomers
- Which of he following is the slowest-reacting leaving group?
A. OH–^ B. Br–^ C. CF 3 SO 3 –^ D. H 2 O
- Which of the following statements is NOT true about a reaction represented by the following energy –reaction coordinate diagram: energy
reaction coordinate
A. This diagram can represent any SN2 reaction. B. This diagram can represent any E2 reaction. C. This diagram can represent any exothermic reaction. D. This diagram can represent any endothermic reaction
- Which of the following solvents will accelerate SN2 reactions between methyl iodide and KOH the most?
A. DMSO B. water C. petroleum ether D. acetic acid
- What is the IUPAC name of the compound shown?
Br (^) Cl
HO
H
H
CH 3
CH 3
Cl
A. (2S,3R,4R)-3,4-dichloro-3-bromo-pentanol B. (2R,3S,4R)-3-bromo-3,4-dichloro-2-pentanol C. (1R,2S,3R)-3-bromo-3,4-dichloro-1-methyl-pentanol D. (2R,3S,4S)-3-bromo-3,4-dichloro-2-pentanol
- Which of the following is a meso compound?
A. B.
C. D.
I
I
I
I
I
I
I
I
- What is the relationship between the following two compounds?
A. Structural isomers B. Not related C. Geometric isomers D. Same
- Which of the following compounds reacts FASTEST in SN1 reactions?
A. (CH 3 ) 3 COH B. (CH 3 ) 3 CI C. (CH 3 ) 3 CNH 2 D. (CH 3 ) 3 CBr
- Which of the following statements is TRUE about the reaction shown?
H C OCH 3
OH
I
OH-
A. The product is achiral. B. OH-^ is acting as a base. C. The reaction happens with racemization. D. The reaction happens with retention of configuration.
- What is the IUPAC name of the compound shown below?
H
H
H
CH 3
C(CH 3 ) 3
CH 2 CH 3
A. 4-Ethyl-2,2-dimethylpentane B. 2,2,4-Trimethylhexane C. 2-Ethyl-4,4-dimethylpentane D. 1- tert- butyl-2-ethylpropane
- Which of these molecules does NOT have a plane of symmetry?
H OH
Br
H H
F
OH
CH 3
H
H
H
C
CH 3
CH 3 CH 2
H Br
A. B. C. D.
F OH
CH 3
- Which of the following compounds would undergo an Sn2 reaction most RAPIDLY?
A. 1-chloropentane B. 2-chloro-2-methylbutane C. 2-chloropentane D. Neopentyl chloride
- In the substitution reaction of CH 3 Br with OH-^ , doubling the concentration of both the substrate and the nucleophile leads to
A. No change B. Doubling of the rate C. Tripling of the rate D. Quadrupling of the rate
- What is the major product of the following reaction?
Br
+ CH 3 S ----->?
A. B. C. D.
SCH 3 SCH 3
