Chemistry234
Chapter17ProblemSet
1. DeterminetheIUPACnameforeachalcohol-containingcompoundshownbelow.
OH
Br
Cl
OH
OH OH
OH
OH
2. Foreachcompoundbelow,listthetype(s)ofintermolecularforcesthatarepresent.
HydrogenBonding(HB);Dipole-DipoleInteractions(DD);vanderWaalsInteractions(VDW)
OH
O
O
OH
Br
O
3. Foreachseriesofcompoundsbelow,rankthecompoundsinorderofincreasingboilingpoint.
Labelthecompoundwiththehighestbpas“1”andthelowestbpas“3.”
a.
b.
c.
NH 2
Cl
NH 2
N
OH
OH
Page 1 of 5
Chem.234–Chapter17ProblemSet
OH
d.
O
e.
4. Writethemajororganicproductandthecompletereactionmechanismforeachreactionshown
below.
H 3O+
H 3O+
OH
I
H 2O
I
Page 2 of 5
Chem.234–Chapter17ProblemSet
5. Drawthemajororganicproductforthereactionofeachalcoholbelowwiththegivenacid.
HBr
HO
OH
HI
HI
6. Predictthemajororganicproductforeachreactionbelow.Ifthereactiondoesnotproceedunderthe
specifiedconditions,writeNoReaction.
OH
OH
PBr 3
OH
PCl 3
OH
SOCl2
Pyridine OH
PBr 3
SOCl2
OH
OH
Pyridine
PBr 3
HBr
OH
OH
PCl 3
Page 3 of 5
Chem.234–Chapter17ProblemSet
7. Predicttheproductsandshowthemechanismforthereactionbelow.
OH
TsCl
Pyridine 8. Predicttheproductforthereactionofeachalkyltosylatebelow.
Na
OTs
NaCN
OTs
OTs
SH
9. Predictthemajororganicproductforeachdehydrationreactionshownbelow.
OH
POCl 3
Pyridine
POCl 3
OH
OH
Pyridine
POCl 3
Pyridine
Page 4 of 5
Chem.234–Chapter17ProblemSet
10. Predicttheproductforeachofthereactionsbelow.
1. OsO4
2. NaHSO 3
1. OsO4
2. H 2O2
1. OsO4
2. H 2O2
11. Providethenecessaryreagentstoaccomplishthefollowingtransformations.
OH
CN
OH
CN
12. Explainthedifferentproductsthatyougetbyvaryingthereactionconditionsbelow.
CN
POCl 3
Pyridine
OH
H 2SO 4
Page 5 of 5