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Chemistry233Chapter1ProblemSet
1) DrawavalidLewisstructureforeachcompoundbelow.
2) DrawavalidLewisstructureforeachcompoundbelow.Assumetheatomsarearrangedasshown.
3) Foreachcompoundshownbelow,determinethenumberofhydrogenpresentoneachcarbon
atom.
C4H10 C4H8 C4H6
C4H8Cl2 C3H9N C4H8 (ring)
PH3 CH3OH BF3Note: B will not have a full octet.
CH2N2 HCO2Cl C5H8O
H C N N
H
H O C Cl
O C
C C
C C
O
O
H2N N
yJ H H H H H H HZ l l l l H H HTri H C C C C H t l l l l lµ l l l l C C C H H C C C Ho H H H H l l t l l
if s H H H H HoG fO o H HS H Hic t ti H H H H l I
e l l l l l l H C c Hof H C C d d h H C C C N 1 185 l I i f f H H H C C H
H H H H l If t H Hv Os Ivit g f H i'te j o I II e z H P H H C O H BO e t l l s
p24N H H F
i11 11
We will goor into charges He H
in cuz It HI
H f N N H l l HH HH
z 3I o z o o 3 3z o 2 2 z 3 z 3 z
3 31 or On carbon takesthe place of one H
Answer Key
Chem.233–Chapter1ProblemSet
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4) Determinethehybridizationofeachnon-hydrogenatominthecompoundsbelow.
5) Predicttheelectrongeometryaroundeachindicatedatombelow.
6) Classifyeachbondusingσandπ.Listthenumberofeachbondtype(i.e.1σ&2πbonds).
HC C CH
CH3
CH3H3C C O
CH3
CH3 C
H
C
H
HH2C
C
O
H
SH
H O H
H
H2C
HC C N H3CCH2
H3CCH2
HC
HCN
CH
CH
HC
H3CO
O
NO
F
H3C CH3
H
H3C CH3
H
N
H2C C CH2
HOH2C CH
HC C C C C CH
HCH2C
H2C C
H
H2C
OHH2C CH3
enanthotoxin:a poison isolated from hemlock
O
F
H
N
T fsp24 groups sp A
ySP spz
3groups SPZ spT tf JP SP ga iPsp2 groups sp sp2
singlebond double SP's spzbond triplebond fSP 9and lone paireach p p Sp3Count as onegroup sp2 Spis not a group
all C7 i
T N TStp Sp sp2 Gp3
i
tetrahedraltrigonal tetrahedralplanar trigonalplano
tetrahedral tetrahedral trigonalplanar linear
tetrahedral tetrahedraltrigonal linear trisonalPlana planar
Felt o oT
o r
o0 IT21T
Chem.233–Chapter1ProblemSet
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7) Foreachbondindicatedinthestructuresbelow,determinetheorbitalsthatmakeupthatparticularbond.
8) Considerthemoleculeshownbelow:a. Ranktheindicatedbondsinorderofincreasingbondlength.
b. Ranktheindicatedbondsinorderofincreasingbondstrength.
9) Answerthefollowingquestionsabouteachmoleculeshownbelow.
H3C HH2C
HC
HC C CH3H
H3CC
H
O
H3CO
CH3 H3CO
CH
CH2H2C C CH2
H3CC
CH3
CH3H
a
b
1. Label the shortest bond.2. Label the shortest C-C single bond.3. Label the weakest C-C bond.4. Label the strongest bond5. Label the strongest C-H bond6. Explain why bond a and bond b are different lenghts.
N
NCH3
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?
Nicotine
a
b
c
d
e
Gp2HCSPGpt 2 9Cp p Op
Gp205ps
GpsHs HsCsp CspGp3Gp2Gp2 Gp2 HsCpCp
Osp3Csp3 Gp3Gp2 CspCspCp Cp
Gp3Gp3
acerbsdec
cadsbcesa
weakest
Shortest
f Singlebond
ystrongestShortest e A longer CspsCsps
Strongest C H b Shorter Gp3Gp2Csp Hs TMursCharacter
gp3 tetrahedral
Sptrigonal Ifpiano best Nin kN
sinceoneofthe Isp's in350ms is a orbital SpZorbitaltunepair
Chem.233–Chapter1ProblemSet
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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
I includedlonepairsH NotrequiredonKekule
HGH H HI 1
H c c c Hl I i OHH f H H HH
iii neHCt
H HHdH HyHl it it IHd c c c c Bi y BrI't l H I HH f H H f HH H
govt ad coat B gt H Br o ITOHIlC OH 0
in Biw y Br
i
i i c
Ipartially condensed the CBsnaps bynot drawing out the CHbonds
Chem.233–Chapter1ProblemSet
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11) Converteachstructurebelowtoafullycondensedstructure.
12) Draweachofthefollowingasskeletalstructures.
H C
H
H
C C
H
H
H
H
C
H
H
C CH3
CH3
CH3
H3C C
Cl
H
C C
H
H O
C
H
H
C
CH3
CH3
H
O
N
C CH
H H
CH
H
CH
H
CH3
C CH3CH2C
H2C CH3
H2C
H2C CH2
CH2
H2C H2C
H2C CH2
CH2
CH2O
H3C C C
H3C
H3C
C C
Cl
C H
CH3
CH3
H
H
HH
H
NCH
CH
CHHCH3C
Clb CHIC CHS
CHGCH Cl CHzC0CHzCH CBLor CHGCHCICHzcocltz.CH CBL
single atom doesnotneedto be put in
Hg Clt OCH CBL agroup ofatomsi.e OH would requireparentheses
CHsCHzN CBCHzCHg or CHEKzNCHz
injiggaasus
IT better
ne okay
I
