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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