1
Cl
2
hν
CH3+
ABC
D
Chem 313 Exam 2 Fall 2000
Name:______________________ SSN: __________________
1. (6) Circle the secondary alcohols and alkyl halides.
Br Cl
OH
F
OH
OH
2. (5) Which of the following is not a good method to make bromocyclopentane?
a) cyclopentanol plus HBr b) cyclopentanol plus PBr3c) cyclopentanol plus NaBr
d) cyclopentane plus Br2 with light e) iodocyclopentane plus KBr in acetone
3. (4) Arrange the following alcohols in order of decreasing reactivity with HBr.
O
H
OH OH
OH
ABCD
a) C>B>D>A b) A>C>B>D c) D>B>C>A d) B>C>A>D e) D>A>C>B
4. (4) Arrange the following carbocations in order of decreasing stability (most stable first).
a) B>D>A>C e) B>A>C>D
b) C>A>B>D f) B>A>D>C
c) D>C>A>B
d) D>B>A>C
5. (6) How many monochlorination products could form in the following reaction?
a) 1 b) 2 c) 3 d) 4 e) 5 f) 6 g) 7
6. (4) Circle the most stable radical.
CH2
7. (6) How many constitutional isomers of C5H10 , including stereoisomers, are possible?
Draw them out if you wish - you get credit for all isomers that you come up with.
