Brian Dorich
Organic Chemistry Quiz #7
Quiz #7 – Due October 17th 5:00 pm
1 (3 pts). Which of the following terms best describes each pair of compounds shown:
enantiomers, diastereomers or the same compound?
A. CH
3
OH
H3C
HO
CH3
CH3
B.
Br
OH
HO
H
H
OH
Br
OH
CH3
CH3
C.
OH
OH
C
H3C
H
CH2OH
H
CH2OH
C
CH3
A. enantiomers
B. diasteriomers
C. same compound
2. (1 pt) Describe what the term stereospecific means to a chemical reaction.
The term stereospecific refers to a reaction in which different stereoisomers react
to give different stereoisomers of product. Example cis-1-bromo-3-methylcyclopentane has an
SN2 reaction where OH- removes the Br inverting the product to produce trans-3methylcyclopentanol.
3. Using Saytzeff’s rule, choose the most stable alkene among the following.
A. 1-methylcyclohexene
B. 3-methylcyclohexene
C. 4-methylcyclohexene
D. They are all of equal stability.
Correct Answer A.
4. Outline the steps that would be used to complete the following transformation.
H3C
hv
Br2
H3C
H3C
H3C
C
+
+
Br
+
Br
+
H
C
CH3CH2O
H
+
+
CH3
Br
Br
H3C
Br2
CH3CH2O-
H3C
C
Br
H3C
+
+
+
BrH
Br
OH2CH3C
+
Br
5. Speculate about the stereochemistry at the chiral carbon in the final product shown above.
Will both enantiomers be present? Will one enantiomer be in higher concentration than the
other? There is no enantiomer present because two groups coming off the central carbon are the
same.