Chemistry233
Chapter10ProblemSet
1) RankeachseriesoforganohalidesinorderofincreasingC-Xbondstrength.
a)
Br
F
b)
Br
Br
c)
I
Br
H 3C
Cl
Cl
Cl
Br
Br
Cl
2) Classifyeachhalogenineverymoleculebelowas:1°,2°,3°,allylic,benzylic,vinyl,oraryl.
F
Cl
I
Br
I
Cl
Cl
Br
Cl
3) Ranktheradicalspeciesbelowinorderofincreasingstability.
CH 3
4) Foreachpair,circlethemoleculethathasthestrongerindicatedbond.Hint:strengthcanbe
assessedbyconsideringthestabilityoftheresultingradicalsfrombondhemolysis–Astrongerbond
willresultinlessstableradicals.
a)
b)
c)
d)
H
H
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Chem.233–Chapter10ProblemSet
5) Drawallrelevantresonancestructureforeachoftheradicalspeciesshownbelow.
a)
b)
c)
6) Ineachcompoundbelow,circletheHthatismostlikelytobeabstractedbyBrŸradical.Youwill
needtodrawinthehydrogen.
7) RanktheC-Hbondsinthestructurebelowinorderofincreasingbondstrength.
H
H
8) Predicttheproductsfortheradicalchlorinationreactionsshownbelow.
H
Cl2
a)
b)
c)
d)
Heat
Cl2
hv
Cl2
Heat
Cl2
hv
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Chem.233–Chapter10ProblemSet
9) TherearethreeconstitutionalisomerswiththeformulaC5H12.Monochlorinationofoneofthese
isomersyieldsonlyoneproduct.Identifytheisomeranddrawthechlorinationproduct.
10)Predictthemajororganicproduct(s)foreachoftheradicalbrominationreactionsshownbelow.
Br 2
a)
Heat
Br 2
b)
hv
Br 2
c)
hv
Br 2
d)
Heat
11)Provideafullarrowpushingmechanismforthefollowingradicalreaction.Designatethethree
steps:initiation,propagation,andtermination.
Br 2
Δ
12)DrawthestructureofNBS
Br
+ HBr
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Chem.233–Chapter10ProblemSet
13)Predicttheproductsforeachofthereactionsshownbelow.Circlethemajorproduct(s).
NBS
hv
NBS
hv
NBS
hv
14)Writethecompleteelectronpushingmechanismforthereactionshownbelow.
Br
NBS
hv
15)Identifyeachofthefollowingtransformationsasanoxidation[O],reduction[H],orneither(N).
O
Cl
Cl
O
O
OH
OH
O
O
O
O
O
OH
O
Cl
Cl
Cl
OH
O
OH
Cl
H
OH
O
O
Br
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