INTRODUCTORY ORGANIC CHEMISTRY

SAMPLE EXAM II KEY

Professor Merlic UCLA

I. STRUCTURES
1. A. (4) Label each of the following molecules as CHIRAL or ACHIRAL.

CN OH Br Br

O
OH Br

Achiral Chiral Achiral Chiral

B. (3) Voglibose is a new drug for the treatment of diabetes. How many total stereoisomers are
possible for this structure?

OH H
N
HO OH

HO OH OH

OH
Five stereocenters, so 25 = 32 isomers
C. (9) Give examples of pairs of ENANTIOMERIC, DIASTEREOMERIC, and MESO structures.

O O

Enantiomers OH OH
N H2 N H2

OMe OMe

Diasteromers

F F

HO COOH
Meso
HO COOH
II. NOMENCLATURE

2. Name the following compounds.

A. (5)

Cl OH
Br

(1R,2R,4S)-1-Bromo-2-chloro-4-(2-hydroxyethyl)cyclohexane
B. (5)

Br

(3S,6S,7S)-1-Bromo-7-ethyl-6-fluoro3-methyldecane
C.

Bicyclo[3.2.1]-6-octene
D. (5)
F

Cl

(1S,6S,7S,9S)7-Chloro-9-fluorobicyclo[4.2.1]nonane
E. (5)

Br

Z-4-Bromo-2-methyl-4-octene
F. (5)
 OH

(1R, 2R, 4S)-2-Methyl-4-propylcyclohexan-1-ol

IV. SYNTHESIS

4. (18) Give the major product or products, if any, from the following reactions. Pay attention
to stereochemistry if appropriate.

A.
H H
H2
OMe (Racemic)
OMe Pd / C Me
Me

B.
Cl
Cl2
(Racemic)
CCl4
Cl

C.

Br OH
Br2 +
H2O
OH Br
(Racemic) (Racemic)

D.
OH
1) Hg(OAc)2 H2O

OH 2) NaBH4 EtOH
OH

V. MECHANISMS

7. (14) Write a complete mechanism (including arrows) for the following reactions.
A.
OH
Br2
H2O
Br
SEE BOOK CHAPTER 6.
8. (7) Draw a Reaction Coordinate Diagram for the reaction in Question 7. Label Activation
Energies, Transition States, Rate Determining Step, and the compounds at each energy level.

R.D.S. T.S. T.S.

T.S.

EA
E EA
EA
!Hrxn
Br OH2
OH

Br
Br

REACTION COORDINATE

VII. REACTIONS

9. (16) Indicate the reagent or reagents needed to perform each of the following syntheses.

OH
OH

H B
A
Br
D G
D C

F
D
E Br
O
OH Br
H OH

A.
H2SO4 H 2O
______________________________________________________________
B.
1) BH3 THF 2) H2O2 NaOH H2O
____________________________________________________
C.
HBr
______________________________________________________________
D.
Br2
______________________________________________________________
E.
1) OsO4 2) NaHSO3 H2O
_______________________________________________________________
F.
1) O3 2) Me2S
_______________________________________________________________
G.
D2 Pt catalyst
_______________________________________________________________
H.
H2 Pt catalyst