ORGANIC CHEMISTRY — CHEM 2210 — SECOND REVIEW EXAM — FALL 1999 - *A*

1. What is the IUPAC name of the compound shown?

H

OH

Cl

A. cis-1-chloro-4-cyclohexanol
B. cis-4-chlorocyclohexanol
C. trans-1-chloro-4-cyclohexanol
D. trans-4-chlorocyclohexanol

2. Which of the following is NOT a product of the reaction shown?

Cl2
CH3 CH2 CH(CH 3 )2
Light

A. CH2 ClCH2 CH(CH 3 )2 C. CH 3 CHClCH(CH 3 )2

B. CH3 CH2 CCl(CH3 )2 D. CH3 CH2 CCl2 CH3

3. Give the IUPAC name of :

H

Cl CH3
Br Cl
HO CH3

A. (2R,3S,4S)-3-bromo-3,4-dichloro-2-pentanol
B. (1R,2R,3R)-2-bromo-2,3-dichloro-1,3-dimethyl-propanol
C. (1R,2S,3R)-2-bromo-1,2-dichloro-1,3-dimethyl-3-propanol
D. (2R,3S,4R)-3-bromo-3,4-dichloro-2-pentanol
4. Which of the following compounds is chiral?
Cl Cl
A. B.

Cl
Cl
Cl
Cl
C. Cl D.

Cl

5. Which of the following compounds reacts the FASTEST as a substrate in an SN1 reaction?

A. (C6 H5 )3 COH B. (C 6 H5 )3 CI C. (C6 H5 )3 CSH D. (C 6 H5 )3 CCl

6. Which of the following statements is true about the following reaction?

CH2 Cl

OH-
H C OCH3
SN2
CH2 OH

A. The product will have R configuration.

B. The product will not have a stereocenter.
C. The product will have S configuration.
D. The reaction will happen with racemization.

7. Which of the following is the most stable conformation of cis-1,3-dimethylcyclohexane?

CH3 CH3 CH3
A. B.
CH3

C. H3 C CH3 D. H3 C
CH3
8. Which of these cycloalkanes shows cis-trans isomerism?

A. B. C. D.

9. Which of the following is (2R,3R)-2,3-diaminobutane?

CH3 CH3 CH3 CH3

H NH2 HN H H NH2 H2 N H
A. B. H2 N H C. H N H D. H NH2
H NH2 2 2

CH3 CH3 CH3 CH3

10. Which of the following is the most stable carbocation having the molecular formula C4 H9 +?

CH2 H H2
A. H3C CH3 B. C. C CH3 D. H C C CH2
CH3 H3C C 3 C
CH3 H H2
CH3 H2

11. Which of these structures is NOT the product of the following reaction?
CH3
CH3 CH3OH
C C + CH3O-
H H2
Br

CH 3
H3C CH 3 H3C H H3C H CH 3
A. C C B. C C
CH 3 C. C C D. H C C
H H H H OCH 3 H2
OCH3

12. Which of the following sets of reagents and conditions will complete the following
reaction?
? Cl
+ ?

A. Cl2 , Ni or Pt catalyst
B. aqueous HCl, heat
C. CH3 Cl, light
D. Cl2 , light
13. Which of the following compounds has a meso stereoisomer?

OH
Cl H

A. CH 3 CH 2 CHCHCH 3
B. C C

HO H Cl

Cl
Cl Cl

C. CH 3 CHCH 2 CHCH 3 D. C C

Cl H H

14. Consider the following molecule:

CH(CH3)2

Br
Cl
CH3
H
CH2CH3
If Br and CH3 group switch their places, what would the relationship between the new
molecule and the one above be?

A. Constitutional isomers
B. Same compound
C. Enantiomers
D. Diastereomers

15. Which of the following structures is the LEAST stable?

H CH2 CH3 H3 C CH2 CH3

A. C C H B. C C H
H H
H3 C H H H

H H H CH2CH3
H H
C. C C H D. C C H
H3C CH2 CH3 H3C H
16. Which of the following conditions are suitable for the synthesis of 2,2-dimethylbutane?

I. CH3 CH2 Br with Li, then CuI, then (CH3 )3 C-Br

II. (CH3 )3 CCH2 -Br with Li, then CuI, then CH3 Br
III. (CH3 )3 C-Br with Li, then CuI, then CH3 CH2 Br

A. I and II only B. I and III only C. II and III only D. II only

17. A particular sample of compound Z containing a mixture of the R and S enantiomers has a
specific rotation of +15.0 degrees. The specific rotation of the pure S enantiomer of
compound Z is –50.0 degrees. What is the % optical purity of this sample, and how much
of the S enantiomer is present?

A. 70%, 30% S B. 30%, 35% S C. 30%, 65% S D. 35%, 70% S

18. Which of the following is a feature of an E2 reaction?

A. The rate of reaction depends on the concentration of base.

B. It is a two step process.
C. It goes via a reactive intermediate.
D. It is faster in more polar solvents.

19. What is the name of the compound shown?

CH3
| H
CH3 CH CH3

H CHCH 2 CH3
|
H CH3

A. 2-ethyl-4,5-dimethylhexane
B. 5-ethyl-2,3-dimethylhexane
C. 3,5,6-trimethylheptane
D. 2,3,5-trimethylheptane
20. What will be the major product(s) of the following reaction?
H Cl
CH3 CH2 OH
+ I ----------------> ?
25˚C
H3 C H

H H H I H

H3 C I H3 C H H3 C
I II III

A. I only B. II only C. III only D. Equal amounts of I and II

21. The reaction of 2-methylbutane with chlorine in the presence of UV light will yield ___
compounds (including stereoisomers) of molecular formula C5 H11 Cl, of which ___ are
optically active. The total number of fractions that can be isolated by distillation is ___.

A. 4, 2, 4 B. 6, 4, 4 C. 6, 4, 2 D. 4, 4, 4

22. What is the relationship between the structures shown?

H F
H H
F H
F F

A. Enantiomers
B. Diastereomers
C. Same compound
D. Structural isomers

23. Molecule A is the enantiomer of molecule B. Molecule B is a stereoisomer of molecule C

but NOT its mirror image. What is the relationship between A and C?

A. Same compound B. Enantiomers C. Diastereomers D. Constitutional isomers

24. Which of the following statements about the relative stabilities of the structures shown is
TRUE?
CH3 H
H H H CH3
I II
H H H CH3
CH3 H

A. II has more steric strain.

B. II has more torsional strain.
C. I has more steric strain.
D. I has more torsional strain.

25. While studying the reaction [RBr] [CH3 ONa] Relative Rate
below, a chemist obtained the 0.01 0.01 1
rate data shown at right. What 0.01 0.02 2
is the mechanism of this reaction? 0.02 0.01 2

CH3 CH2 CH2 Br + CH3 ONa -----> CH3 CH2 CH2 OCH 3 + NaBr

A. SN1 B. SN2 C. E1 D. E2