Post on 20-Mar-2018
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Chemistry234Chapter19-ProblemSet
Nomenclature1) GivetheIUPACnameforeachaldehydebelow.
2) GivetheIUPACnameorstructureforeachketonebelow.
3) GivetheIUPACnameforeachpolyfunctionalcompoundbelow.
O
HH
OBr
O H
ClCl
OBr
O Ogive IUPAC and common anmes
3-phenylcyclopentanone 4-chloro-3-methyl-2-hexanone methyl propyl ketone
OOH
OH
O Br
O
OH
O
NH2
O
O
HO
H
O
(NH2 is an amino substituent)
O
Chem.234–Chapter19ProblemSet
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PropertiesandReactivityofAldehydesandKetones4) Rankthecompoundsineachgroupinorderofincreasingreactivitytowardsnucleophilicattack.
5) Ineachpairbelow,determinewhichcompoundwouldexistasthehigherpercentageofhydrateinthepresenceofwateratequilibrium.Explainyourchoice.
6) ChallengeProblem:Explainwhythehydrate(gem-diol)isthemajorspeciespresentatequilibriumwhencyclopropanoneisdissolvedinwater.
O
H H
O
H
O
O O O
O
H
O
H
O
H
O
H
O
HCl
O
HCl
Cl
a.
b.
c.
d.
O
H
O
O
O
H
O
F3C
O
H H
O
F3C
O
H Br3C
O
H
O
HO
H
Chem.234–Chapter19ProblemSet
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ReactionsandMechanisms7) Drawtheproduct(s)foreachreactionbelow.
8) Drawthemechanismforthereactioninpartbofquestion7.
H
O+
NH2 traceH+
OHO
OH
H+
N H+/H2O
ONH
traceH+
OOH
CH3OH
H+
H
O CH3OH
H+
NH+/H2O
OCH3OCH3
H+/H2O
+
a.
b.
c.
d.
e.
f.
g.
h.
Chem.234–Chapter19ProblemSet
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9) Drawthemechanismforthereactionofpartcofquestion7.
10) Drawthemechanismforthereactionofparthofquestion7.
11) Etoposideisusedforthetreatmentoflungcancer,testicularcancer,andlymphoma.Circleeveryacetalinetoposide.WhatproductswouldbeformedifetoposidewerehydrolyzedwithH+/H2O?
O
OO
O
O
H
H
OCH3OH
H3CO
OO
O
H
HOH
HO
Chem.234–Chapter19ProblemSet
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12) DrawtheproductsformedineachWittigreaction.Drawallstereoisomersformedwhenamixtureofproductsresults.
13) Drawthemechanismforthereactioninparteofquestion12.
O
Ph3P
+
O
H
PPh3
Ph H
O
Ph3P
+
+
Cl1. PPh3
2. BuLi3. acetone
PhBr 1. PPh3
2. BuLi3. PhCHO
Cl 1. PPh3
2. BuLi3. CH3CH2CHO
a.
b.
c.
d.
e.
f.
Chem.234–Chapter19ProblemSet
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Synthesis14) WhatWittigreagentandwhatcarbonylcompoundareneededtoprepareeachalkene?
15) Providethefinalproductuponthesequenceofreactionsbelow.
16) Fillinthemissingproductsineachboxbelow.
Ph OEt
O
O
OCH3
1. LiAlH42. H2O3. PBr34. Mg5. (CH3)2C=O6. H2O
O
PPh3
H2Pd/C
H+
Br2
OBr O
O
Na
SN2HO
OH
H+
1. PhMgBr2. H3O+
H+
H2O
+
Rxn with acetal only
PBr3Pyridine
(Elimination)
O
H+
H2N
H+
H2O
Chem.234–Chapter19ProblemSet
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17) Provideareasonablesynthesisforthecompoundshownbelow.
18) Provideareasonablesynthesisforthecompoundshownbelow.
19) Provideareasonablesynthesisforthecompoundshownbelow.
OHBr
? OPh
O
O O ? OH O
OH?