Chemistry233
Chapter8ProblemSet
AdditionofHXToAlkenes
1. Predicttheproductsforeachofthefollowingreactions.Ifthereactiongeneratesanewchiral
center,takethatintoconsiderationwhendrawingtheproducts.
a.
b.
c.
H Cl
H Br
H Cl
d.
H Br
e.
H I
f.
H Cl
h.
H Br
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Chem.233–Chapter8ProblemSet
2. Showthefullarrowpushingmechanismforthereactioninpartf(above).
3. Showthefullarrowpushingmechanismforthereactioninparth(above).
4. Drawasimpleenergydiagramforthereactioninparth.Labelyourstartingmaterial,
product,andeachintermediate.
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Chem.233–Chapter8ProblemSet
AdditionofH+andH2OorHORtoAlkenes
5. Predicttheproductsforeachofthefollowingreactions.Ifthereactiongeneratesanewchiral
center,takethatintoconsiderationwhendrawingtheproducts.
a.
H 2SO 4
H 2O
b.
H 3O
c.
H 2SO 4
OH
d.
H 3O
6. Showthefullarrowpushingmechanismforthereactioninpartc(above).
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Chem.233–Chapter8ProblemSet
HalogenationofAlkenesandHalohydrinFormation
7. Predictthemajorproductsforeachofthefollowingreactions.Besuretoindicate
stereochemistrywhereappropriate.
a.
b.
c.
Br
Br
Br
Br
Br
Br
H 2O
d.
Cl
Cl
e.
Br
Br
OH
f.
Br
Br
NH 2
g.
h.
Cl
Cl
Cl
Cl
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Chem.233–Chapter8ProblemSet
8. Showthefullarrowpushingmechanismforthereactioninpartc(above).
9. Showthefullarrowpushingmechanismforthereactioninpartd(above).
10. Showthefullarrowpushingmechanismforthereactioninpartf(above).
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Chem.233–Chapter8ProblemSet
Hydroboration/Oxidation
11. Predictthemajorproductforeachofthehydroboration-oxidationreactionsshownbelow.
a.
1. BH 3 • THF
2. H 2O2, NaOH
b.
1. BH 3 • THF
2. H 2O2, NaOH
c.
1. BH 3 • THF
2. H 2O2, NaOH
d.
1. BH 3 • THF
2. H 2O2, NaOH
12. Showthefullarrowpushingmechanismforthehydroborationstepinpartb(above).
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Chem.233–Chapter8ProblemSet
13. Showthefullarrowpushingmechanismfortheoxidationstepshownintheboxbelow.
Youdonothavetoknowthismechanismstepfortheexam,butgiveitashot.
BH 3 • THF
H 2O2, NaOH
B
O
B
O
O
NaOH(aq)
NaO
3
OH +
ONa
B
ONa
Dihydroxylation
14. Predictthemajorproduct(s)foreachofthefollowingreactions.
OsO4
NMO
Acetone, H2O
OsO4
NMO
Acetone, H2O
OsO4
NMO
Acetone, H2O
Cyclopropanation
15. Predictthemajorproduct(s)foreachofthefollowingreactions.
CH2I2
Zn(Cu)
CH2I2
Zn(Cu)
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Chem.233–Chapter8ProblemSet
AlkeneHydrogenation
16. Predictthemajorproduct(s)foreachofthefollowingreactions.Showstereochemistrywhere
appropriate.
a.
H2
Pd/C
b.
H2
Pd/C
c.
H2
Pt
d.
H2
Ni
e.
H2
Pt
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Chem.233–Chapter8ProblemSet
SynthesisInvolvingReactionsofAlkenes
17. Identifythereagent(s)thatyouwouldneedtoaccomplishthefollowingtransformations.
a.
b.
c.
OH
Br
Cl
d.
e.
OH
O
f.
Cl
Cl
+
Enantiomer
+
Enantiomer
g.
Cl
OH
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Chem.233–Chapter8ProblemSet
“Challenge”Problems(Notreallyallthatchallenging…)
18. Drawthestructureofthealkenethatwasusedineachofthefollowingreactions.The
molecularformulaofthestartingmaterialisprovided.
H 2SO 4
Br 2
HO
CH 3OH
H 2O
Br
O
C6H10
C5H10
Br 2
BH 3 • THF
Br
Br
C5H10
C6H10
OH
then
H 2O2, NaOH
19. Proposeamechanismforthefollowingreactionandexplaintheregioselectivity(i.e.whydid
theIandtheBrendedupwheretheydid?)
I Cl
I
Cl
20. Proposeamechanismforthefollowingreaction.
OH
Br 2
O
Br
+ HBr
21. Thecarbocationbelowappearstobeaprimarycarbocationyetitisevenmorestablethana
tertiarycarbocation.Explain.
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