Chm 2210 Organic Chemistry Exam Worksheets With Answer Key - Professor A. Herriott Page 4

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12. The bond dissociation energies for the relevant bonds are given below each of the
species involved in the following reaction. Calculate the overall ∆H° for the reaction.
CH
CH
CH
-H
+
Br-Br
CH
CH
CH
-Br
+
H-Br
3
2
2
3
2
2
∆H
=423 kJ/mol ∆H
=193 kJ/mol
∆H
=294 kJ/mol ∆H
o
o
o
o
=366 kJ/mol
A) +616 kJ / mol
D) +57 kJ kJ / mol
B) -101 kJ / mol
E) -44 kJ / mol
C) -173 kJ / mol
13. When 3- methyl-2-pentene is treated with mercuric acetate, Hg(O
CCH
)
, in a THF-
2
3
2
ethanol mixture and the resulting product reacted with NaBH
in basic solution, the
4
principal product formed is which of these?
A) 3-methyl-3-pentanol
D) 2-ethoxy-3-methylpentane
B) 3-ethoxy-3-methylpentane
E) 1-ethoxy-3-methylpentane
C) 3-methyl-2-pentanol
14. What would be the major product of the following reaction?
CH
3
HBr
?
peroxides
CH
3
CH
CH
CH
Br
3
3
3
Br
Br
OR
CH
3
Br
I
II
III
IV
V
A) I B) II C) III D) IV E) V
15. cis-3-Methylcyclopentanol is treated with CH
SO
Cl in the presence of a base. The
3
2
product of the reaction then is allowed to react with KI in methanol. What is the final
product?
A) trans-1-Iodo-3-methylcyclopentane
D) 2-Methylcyclopentene
B) cis-1-Iodo-3-methylcyclopentane
E) 3-Methylcyclopentene
C) 1-Methylcyclopentene
Page 4

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