Download - Chemistry 234 Chapter 17 Problem Set
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Chemistry234Chapter17ProblemSet
1. DeterminetheIUPACnameforeachalcohol-containingcompoundshownbelow.
2. Foreachcompoundbelow,listthetype(s)ofintermolecularforcesthatarepresent.
HydrogenBonding(HB);Dipole-DipoleInteractions(DD);vanderWaalsInteractions(VDW)
3. Foreachseriesofcompoundsbelow,rankthecompoundsinorderofincreasingboilingpoint.
Labelthecompoundwiththehighestbpas“1”andthelowestbpas“3.”
OH
Br OHCl
OH
OHOH OH
OH
O
O
OOH
Br
NH2 Cl
NH2 N
OH OH
a.
b.
c.
Chem.234–Chapter17ProblemSet
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4. Writethemajororganicproductandthecompletereactionmechanismforeachreactionshownbelow.
OH Od.
e.
H3O+
H3O+
OHI
IH2O
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5. Drawthemajororganicproductforthereactionofeachalcoholbelowwiththegivenacid.
6. Predictthemajororganicproductforeachreactionbelow.Ifthereactiondoesnotproceedunderthe
specifiedconditions,writeNoReaction.
HO
HBr
OHHI
OHHI
OH
OH
PBr3
PCl3
OH SOCl2Pyridine
OH
OH
PBr3
SOCl2Pyridine
OHPBr3
OHHBr
OHPCl3
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7. Predicttheproductsandshowthemechanismforthereactionbelow.
8. Predicttheproductforthereactionofeachalkyltosylatebelow.
9. Predictthemajororganicproductforeachdehydrationreactionshownbelow.
OHTsCl
Pyridine
OTs
OTsNaCN
OTs SH
Na
OH POCl3Pyridine
OH
POCl3Pyridine
OH POCl3Pyridine
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10. Predicttheproductforeachofthereactionsbelow.
11. Providethenecessaryreagentstoaccomplishthefollowingtransformations.
12. Explainthedifferentproductsthatyougetbyvaryingthereactionconditionsbelow.
1. OsO4
2. NaHSO3
1. OsO4
2. H2O2
1. OsO4
2. H2O2
OH CN
OH CN
CN
OH
POCl3Pyridine
H2SO4