Name:

Quiz 4 Summer 2009

Problem 1 (10 points): Circle each chirality center in the molecules below, and assign the
correct stereochemical identifier (R or S) to each. Name the first molecule according to IUPAC
rules with the correct stereochemistry.
OH

CH3
Cl

Cl F
H

Problem 2 (4 points): Answer the following questions based on the three stereoisomers of
1,2,3,4-tetrabromobutane.

(a) One isomer is sweet and has an optical rotation of 0. Circle the sweet isomer.
(b) A mixture of the two non-sweet compounds (which are enantionmers) has a
specific rotation of 9. The R,R isomer has a specific rotation of 12. What is the
enantiomeric excess?

Problem 3 (2 points): A second category of six-carbon carbohydrates, called ketohexoses, has

the constitution shown. How many stereoisomeric 2-ketohexoses are possible?

Problem 4 (16 points): In the box below each pair of molecules, write the letter(s) for each label
from the list below which applies to the molecules. Be careful: many (most) pairs fit more than
one descriptor, so be sure to write any and all applicable letters. Also note that for every pair,
you should write either "J" or "K", since all molecules are either chiral or achiral. All letters will
not necessarily be used. Also, for I, J, and K, both compounds or neither will be meso, chiral, or
achiral. Do not put letters which are not applicable -- points will be taken off for each incorrect
letter.
A. Not isomers
B. Identical compounds
C. Constitutional Isomers
D. Stereoisomers

E. Conformational isomers
F. Configurational isomers
G. Enantiomers
H. Diastereomers

OH

OH

OH

I. Meso compounds
J. Chiral
K. Achiral

Cl

OH

Cl