Chemistry233
Chapter1ProblemSet
1) DrawavalidLewisstructureforeachcompoundbelow.
C 4H10
C 4H 8
C 4H 6
C 4H 8Cl2
C 3H 9N
C 4H 8 (ring)
PH 3
CH 3OH
BF 3
Note: B will not have a full octet.
2) DrawavalidLewisstructureforeachcompoundbelow.Assumetheatomsarearrangedasshown.
CH2N 2
H
HCO2Cl
C
N
N
H
O
H
C5H 8O
C
O
Cl
C
O
C
C
C
C
3) Foreachcompoundshownbelow,determinethenumberofhydrogenpresentoneachcarbon
atom.
O
H 2N
N
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Chem.233–Chapter1ProblemSet
4) Determinethehybridizationofeachnon-hydrogenatominthecompoundsbelow.
CH 3
CH 3
HC
C
H 3C
CH
O
C
O
C
CH 3
CH 3
H
C
H
H
O
C
H 2C
SH
H
H 2C
H
CH2
N
C
HC
H
H
H 3C
H
C
HC
CH2
H 3C
CH
HC
O
H 3C
CH
N
5) Predictthemolecularshapearoundeachindicatedatombelow.
O
O
N
N
H
H
F
H 2C
H 3C
CH 3
H 3C
C
CH 3
CH2
OH
HO
H2
C
CH
HC
HC
C
C
C
C
H2
C
H2
C
C
H
H2
C
H2
C
CH 3
CH
enanthotoxin:
a poison isolated from hemlock
6) Classifyeachbondusingσandπ.Listthenumberofeachbondtype(i.e.1σ&2πbonds).
N
O
F
H
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Chem.233–Chapter1ProblemSet
7) Foreachbondindicatedinthestructuresbelow,determinetheorbitalsthatmakeupthat
particularbond.
H 3C
H
CH 3
H 3C
C
C
CH 3
C
H 3C
H
CH 3
CH2
O
O
H
H
H 2C
H 3C
O
H
C
H 2C
C
H
C
H
CH2
C
H 3C
CH 3
8) Considerthemoleculeshownbelow:
a. Ranktheindicatedbondsinorderofincreasingbondlength.
d
b
b. Ranktheindicatedbondsinorderofincreasingbondstrength.
e
c
a
9) Answerthefollowingquestionsabouteachmoleculeshownbelow.
a
1. Label the shortest bond.
2. Label the shortest C-C single bond.
3. Label the weakest C-C bond.
4. Label the strongest bond
5. Label the strongest C-H bond
6. Explain why bond a and bond b are different lenghts.
b
N
N
CH 3
Nicotine
1. What is the hybridization of each N atom?
2. What is the geometry around each N atom?
3. In what type of orbital does the lone pair in each N reside?
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Chem.233–Chapter1ProblemSet
10)ConverteachcondensedstructurebelowtoaKekulestructureandaskeletalstructure.
Condensed
Kekule
Skeletal
(CH3)2CH(CH2)2OH
CH3(CH2)3CH(Cl)CH3
(CH3)3CCH2C(CH3)2CH2Br BrCH2OCH2CO2H
H2NCH2N(CH3)CH2Br
CH3(CH2)3CCl(CH3)2
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Chem.233–Chapter1ProblemSet
11)Converteachstructurebelowtoafullycondensedstructure.
H H H H CH 3
H
C
C
C
C
C
H
H
H
H
CH 3
H 3C
CH 3
Cl H O H
CH 3
C
C
C
C
H
H
H
CH 3
C
H
O
N
12)Draweachofthefollowingasskeletalstructures.
H
H
C
C
H
H 3C
H
C
H
C
H
H
C
H 3C
C
H 3C
CH 3
H2
C
H 2C
CH2
H 2C
C
H2
H 3C
H2 H2
C C C CH 3
H 2C
H 2C
O
C
H2
CH2
CH2
H
H
H
CH 3
C
C
C
C
H H
H
C
H 3C
N
C
H
H
Cl CH 3
CH
CH
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