Chemistry Exam Worksheet - Chemistry 61, Dr. M.t. Crimmins, The University Of North Carolina At Chapel Hill Page 3
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1
2
3
4
5B
14.
Which of the following would be the least stable carbocation?
+
+
+
+
d.
a.
c.
b.
H
C C
CH
H
C C CH
H
C C
CH–CH
3
3
3
3
H
C C CH
2
3
2
3
H
H
CH
3
C
15. Which of the following would undergo SN2 reaction the fastest?
–
+
a. CH
I + HO
Na
3
–
+
b. CH
CH
I
+ HO
Na
3
2
–
+
c. CH
I + HS
Na
3
–
+
d. (CH
)
CHI
+ HO
Na
3
2
–
+
e. (CH
)
CHI
+ HS
Na
3
2
A
16. Which of the following alcohols would undergo dehydration the fastest?
a. 2-phenyl-2-butanol
b. 2-methyl-2-butanol
c. 2-butanol
d. 1-butanol
C
17. Which of the following is a not stereospecific reaction?
a. epoxidation of cyclohexene with m-CPBA
b. elimination of HBr from 2-bromo-2-methylpropane by sodium ethoxide?
c. dehydration of 1-methylcyclohexanol by heating with H
SO
.
2
4
d. reaction of 2-bromobutane with NaOH.
D
18. Reaction of a secondary alkyl halide with a weak base would likely result in
a. SN1 reaction
b. SN2 reaction
c. E1 Reaction
d. mixture of SN1 and E1
e. E2 elimination
f. mixture of SN2 and E2
B
19. Which of the following is the stronger acid?
a. ethanol
b. ethanethiol
c. acetylene
d. butane
B
20. Which of the following would be the most soluble in water?
a. diethyl ether
b. methanol
c. 1-butanol
d. dimethylsulfide
– 3 –
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