Chemi

str
yrevi
ewer ORGANI
CCOMPOUNDS
Fr
iedr
ichWohl
er-s
ynt
hes
izedur
eaf
rom ammoni
um
VALENCEBONDTHEORYANDCARBONCOMPOUNDS cyanat
e(1828)-di
spel
led t
he bel
ieft
hator
gani
c
-as
sumest
hatt
heel
ect
ronsi
n amol
ecul
eoccupy compoundscoul
donl
ybef
ormedbynat
ure
at
omi
cor
bit
alsoft
hei
ndi
vidualat
oms(
over
lappi
ng= ORGANI
CCHEMI
STRY
bondi
ng) Car
bon-compl
etesoct
etbys
har
inge-s
har
esi
tse-
-opt
imum di
stance bet
ween el
ement
s wher
ethe wi
thot
herCat
omsf
ormi
ngs
ingl
e,doubl
e,andt
ripl
e
at
tract
ivef
orcesoft
henucl
eiwi
llbegr
eat
est
,and bonds-s
har
esi
tse-and r
eadi
lyf
ormsbondswi
th
r
epul
sionwi
llbel
eas
t-account
sfort
hechangesi
n ot
herel
ement
sli
keO,H,N,and t
hehal
ogens-i
ts
pot
ent
ialener
gyast
hedi
stancebet
weent
her
eact
ing s
mal
lradi
usal
lowsi
tto appr
oach anot
herC at
om
at
omschanges cl
osel
y,gi
vingr
iset
oshor
tands
trongcoval
entbonds
HYBRI
DIZATI
ON ands
tabl
ecompounds
-mi
xing ofat
omi
c or
bit
alsi
n an at
om (
usual
lya - br
anch of chemi
str
y t
hat deal
s wi
th car
bon
cent
ralat
om)t
ogener
ateas
etofhybr
idor
bit
als compounds
Hybr
idor
bit
als-at
omi
cor
bit
alsobt
ainedwhent
woor -canbedi
sti
ngui
shedaccor
dingt
ofunct
ionalgr
oups
mor
e nonequi
val
ent or
bit
als of t
he s
ame at
om t
heycont
ain
combi
nei
npr
epar
ati
onf
orcoval
entbondf
ormat
ion -mos
tor
gani
ccompoundsar
eder
ivedf
rom agr
oupof
STEPS: compoundsknownashydr
ocar
bonsbecaus
etheyar
e
1.
Drawt
heLewi
sst
ruct
ureoft
hemol
ecul
e. madeupofonl
yhydr
ogenandcar
bon
2.
Predi
ctt
heover
allar
rangementoft
heel
ect
ronpai
rs Funct
ionalgr
oup -gr
oup ofat
omst
hati
slar
gel
y
(
bot
hbondi
ngpai
rsandl
onepai
rs)us
ingt
heVSEPR r
espons
ibl
efort
hechemi
calbehavi
oroft
hepar
ent
3.
Deduce t
he hybr
idi
zat
ion oft
he cent
ralat
om by mol
ecul
e
mat
chi
ngt
hear
rangementoft
heel
ect
ronpai
rswi
th
t
hos
eoft
hehybr
idor
bit
als Hydr
ocar
bonsar
ecl
ass
ifi
edi
nto:(
bys
truct
ure)
Al
iphat
ichydr
ocar
bonsdonotcont
aint
hebenz
ene
gr
oup,ort
hebenz
ener
ing
Ar
omat
ic hydr
ocar
bons - cont
ain one or mor
e
benz
ener
ings
Al
iphat
ic hydr
ocar
bons ar
e di
vided i
nto al
kanes
,
al
kenes
,andal
kynes
HYBRI
DIZATI
ONWI
THMULTI
PLEBONDS
ALKANES(
CnH2n+2)
Si
gmabond -f
ormed byend-
to-
end over
lap oft
he
-onl
yhaves
ingl
ebonds-al
soknownass
atur
ated
at
omi
cor
bit
alswi
th el
ect
ron dens
ity concent
rat
ed
hydr
ocar
bons(
cont
aint
hemaxi
mum #ofH at
oms
bet
weent
henucl
eioft
hebondi
ngat
oms
t
hatcanbondt
otheC at
omspr
esent
)-i
nnami
ng
Pibond-f
ormedbyt
hes
idewaysover
lapofor
bit
als
al
kanes
,the–
anes
uff
ixi
sus
ed-nameoft
hepar
ent
wi
tht
he el
ect
ron dens
ity concent
rat
ed above and
compoundi
sdet
ermi
nedbyt
henumberofCat
omsi
n
bel
owt
hepl
aneoft
henucl
eioft
hebondi
ngat
oms
t
hel
onges
tchai
n
I
SOMERS
-mol
ecul
est
hathavet
hes
amemol
ecul
arf
ormul
a, C=Cbondoft
heal
kene
butdi
ff
erents
truct
ures -exhi
bitgeomet
rici
somer
s(ci
sandt
rans
)
NAMI
NGALKANES ci
sis
omer-t
wopar
ticul
arat
omsorgr
oupofat
oms
-par
entnameoft
hehydr
ocar
boni
sthatgi
vent
othe ar
eadj
acentt
oeachot
her(
sames
ideoft
hedoubl
e
l
onges
tcont
inuouschai
nofCat
omsi
nthemol
ecul
e bond)
-anal
kanel
essoneHat
om i
sanal
kylgr
oup t
ransi
somer-t
het
wogr
oupsar
eacr
ossf
rom each
-t
he name oft
he compound mus
tindi
cat
ethe ot
her
l
ocat
ionsofCat
omswher
erepl
acement
sar
emade- REACTI
ONOFALKENES
numbereach C at
om on t
he l
onges
tchai
nint
he 1.
Hydr
ogenat
ion-hydr
ogeni
saddedt
ocompounds
di
rect
ion t
hatgi
ves t
he s
mal
ler number
sfor t
he cont
aini
ngdoubl
ebondsus
ual
lyi
nthepr
esenceofa
l
ocat
ionsofal
lbr
anches cat
alys
t
-When t
her
eismor
ethan oneal
kylbr
anch oft
he 2.Addi
ti
onofhydr
ogenhal
ideandhal
ogens(
HX;ex:
s
ameki
ndpr
esent
,weus
eapr
efi
xsuchasdi
-,t
ri-
,or HBr
)
t
etr
a-wi
tht
henameoft
heal
kylgr
oup Mar
kovni
kov’
srul
e-t
headdi
ti
on ofuns
ymmet
rical
-Whent
her
ear
etwoormor
edi
ff
erental
kylgr
oups
, r
eagent
sto al
kenes
,the pos
iti
ve por
tion of t
he
t
henamesoft
hegr
oupsar
eli
stedal
phabet
ical
ly r
eagentaddst
othecar
bonat
om t
hatal
readyhast
he
- al
kanes can have many di
ff
erent t
ypes of mos
tHat
oms
s
ubs
tit
uent
s - s
ubs
tit
uent gr
oups ar
e l
ist
ed ALKYNES(
CnH2n-
2,n=2,
…)
al
phabet
ical
lyi
nthename,andt
hechai
nisnumber
ed -cont
ain atl
eas
tone t
ripl
e car
bon-
car
bon bond -
i
nthedi
rect
iont
hatgi
vest
hel
owes
tnumbert
othe cl
ass
ifi
edasuns
atur
atedhydr
ocar
bons
f
irs
tsubs
tit
utedcar
bonat
om -t
he–
ynes
uff
ix(
endi
ng)i
sus
edi
nnami
ng-nameof
CYCLOALKANES(
CnH2n) t
hepar
entcompoundi
sdet
ermi
nedbyt
henumberof
-al
kaneswhos
ecar
bonat
omsar
ejoi
nedi
nri
ngs Cat
omsi
nthel
onges
tchai
n
REACTI
ONOFALKANES REACTI
ONSOFALKYNES
1.
Combus
tion -unders
uit
abl
e condi
ti
ons
,al
kanes 1.
Combus
tion-pr
oduceCO2andH2O
under
go combus
tion r
eact
ionst
o pr
oduceCO2and 2.
Hydr
ogenat
ion–addi
ti
onofhydr
ogen
H2O 3.
Addi
ti
onofhydr
ogenhal
ideandhal
ogens
2.
Hal
ogenat
ion -one ormor
e hydr
ogen at
omsar
e AROMATI
CHYDROCARBONS
r
epl
acedbyhal
ogenat
oms -mol
ecul
escont
ainar
ingofs
ixcar
bonat
oms(
benz
yl
ALKENES(
CnH2n)
-cont
ainatl
eas
tonecar
bon-
car
bondoubl
ebond
-al
socal
ledol
efi
ns
-cl
ass
ifi
edasuns
atur
atedhydr
ocar
bons
-t
he–
enes
uff
ix(
endi
ng)i
sus
edi
nnami
ng
-nameoft
hepar
entcompoundi
sdet
ermi
nedbyt
he
numberofCat
omsi
nthel
onges
tchai
n
number
sint
henamesofal
kenesr
efert
othel
owes
t
number
edcar
bonat
om i
nthechai
nthati
spar
toft
he r
ing)at
tached-s
impl
estmemberi
sbenz
ene,C6H6
CHEMI
CALBONDI
NG LATTI
CEENERGY
Gi
lber
tLewi
s:f
irs
tsket
chedhi
sideaaboutt
heoct
et
r
uleont
hebackofanenvel
ope
-at
omscombi
nei
nor
dert
oachi
eveamor
est
abl
e
el
ect
ronconf
igur
ati
on
–Coul
umb’
scons
tant –char
ger –di
stance
- maxi
mum s
tabi
li
ty r
esul
ts when an at
om i
s
COVALENTBONDI
NG
i
soel
ect
roni
cwi
thanobl
egas
-bond i
n whi
ch t
wo el
ect
ronsar
eshar
ed by t
wo
OCTETRULE
nonmet
alat
oms-s
har
ed pai
rofel
ect
ronsi
sof
ten
-s
tat
est
hatwhenat
omsofel
ement
scombi
net
ofor
m
r
epr
esent
edbyas
ingl
eli
ne-eachel
ect
roni
nas
har
ed
compounds
,theyt
end t
olos
e,gai
n,ors
har
ee-t
o
pai
risat
tract
edt
othenucl
eiofbot
hat
oms-i
nvol
ves
achi
evet
hes
ameel
ect
ronar
rangementast
henobl
e
onl
ytheval
enceel
ect
rons
gasnear
estt
hem i
ntheper
iodi
ctabl
e
l
onepai
rs— pai
rsofval
enceel
ect
ronst
hatar
enot
LEWI
SDOTSYMBOL
i
nvol
vedi
ncoval
entbondf
ormat
ion
-cons
ist
soft
hes
ymbolofanel
ementandonedotf
or
Di
ff
erentt
ypesofcoval
entbond:
eachval
enceel
ect
roni
nanat
om oft
heel
ement
1.Si
ngl
ebond-t
woat
omsar
ehel
dtoget
herbyone
LEWI
SDOTSYSTEM
el
ect
ronpai
r
-i
ncombi
ningwi
thot
herat
oms
,onl
yout
erel
ect
rons
,
2.Mul
ti
plebonds-t
woat
omss
har
etwoormor
epai
rs
t
heval
encee-
,ar
einvol
ved.Tokeept
rackoft
hes
e
ofel
ect
rons
val
enceel
ect
rons
,theLewi
sdots
ymboli
sus
ed
PROPERTI
ES
CHEMI
CALBOND
-l
ow mel
ti
ngandboi
li
ngpoi
nts-r
elat
ivel
ysof
tsol
ids
-at
tract
ion bet
ween el
ement
s -r
esul
tsf
rom t
he
compar
ed t
oioni
ccompounds-nonconduct
orsof
at
tract
ion ofnucl
eif
orel
ect
rons-t
he pr
otonsi
n
el
ect
rici
tyi
n anyphas
e/f
orms-mos
tlyi
nsol
ubl
ein
nucl
eusar
eat
tract
edt
othee-ofanot
herat
om
wat
er
TYPES:
POLARI
TYOFBONDS
1.I
oni
cBondi
ng
-t
heel
ect
ronss
pendmor
eti
mei
nthevi
cini
tyofone
2.Coval
entBondi
ng
at
om t
hant
heot
her-
”unequals
har
ing”
I
ONI
CBOND
ELECTRONEGATI
VITY
- f
orms i
oni
c compounds
, compounds wi
th
-abi
li
ty ofan at
om t
o at
tractt
owar
dit
sel
fthe
pol
yat
omi
cions-t
rans
ferofe-bet
weenel
ement
s-
el
ect
ronsi
nachemi
calbond
pr
oduct
ionofs
alt
sorcr
yst
als-bet
weenanon-
met
al
-r
elat
edt
oEAandI
E
andamet
alel
ement
-i
fanat
om hasahi
ghel
ect
ronaf
fi
nit
y(t
endst
opi
ck
PROPERTI
ES
upel
ect
ronseas
ily)andahi
ghi
oni
zat
ionener
gy(
does
-har
dsol
idat22degr
eesCel
sius-
hashi
ghmel
ti
ng
not l
ose el
ect
rons eas
ily)
,then i
t has a hi
gh
poi
ntt
emper
atur
e(l
att
ice ener
gy -def
ined ast
he
el
ect
ronegat
ivi
ty
amountofener
gyr
equi
red t
o compl
etel
ysepar
ate
PERCENTI
ONI
CCHARACTER
onemol
eofas
oli
dioni
ccompoundi
ntogas
eousi
ons
-di
ff
erencei
ntheel
ect
ronegat
ivi
tyval
ues(
EN)oft
wo
-
nonconduct
orofel
ect
rici
tyi
nsol
idf
orm/
phas
e-good
bondedat
oms-anel
ect
ronegat
ivi
tydi
ff
erenceof2.
0
conduct
orofel
ect
rici
tyi
naqueousphas
e
orgr
eat
eri
sus
ual
lycl
ass
ifi
ed t
o bepr
edomi
nant
ly canhave>8val
encee-ar
oundt
hecent
ralat
om Ex:
i
oni
c;al
mos
t2or<2i
spol
arcoval
ent-nonpol
arbond SP6,PF5
àel
ect
ronsar
eshar
edequal
lyorevenl
yinabond;e- GEOMETRY OF MOLECULES AND POLARI
TY OF
negdi
ff=0 COMPOUNDS
LEWI
SDOTSYSTEM MOLECULARGEOMETRY
STEPS: -i
sthet
hree-
dimens
ionalar
rangementofat
omsi
na
1.
countt
otalval
encee mol
ecul
e-af
fect
sit
sphys
icalandchemi
calpr
oper
ties
2.
connectcent
ralat
om wi
thot
herat
oms -can be det
ermi
ned by exper
iments
uch asx-
ray
3.
compl
etet
heval
ences
hel
lsofout
erat
oms di
ff
ract
ion
4.
addanyext
rae-t
ocent
ralat
om -as
sumet
hatal
lel
ect
ronpai
rsi
ntheval
ences
hel
l
ar
oundacent
ralat
om r
epeloneanot
her-as
sumea
FORMALCHARGE geomet
ry or or
ient
ati
on t
hat wi
ll mi
nimi
ze t
he
-el
ect
ricalchar
ge di
ff
erence bet
ween t
he val
ence r
epul
sions
el
ect
ronsi
n an i
sol
ated at
om and t
he numberof Val
enceShel
lEl
ect
ronPai
rRepul
sionTheor
y(VSEPR)
el
ect
ronsas
signedt
othatat
om i
naLewi
sst
ruct
ure –appr
oachus
edi
npr
edi
cti
ngmol
ecul
argeomet
ry
VSEPR
•el
ect
ron pai
rss
tay as f
ar apar
t •i
nter
ms of
r
epul
sions
,doubl
eandt
ripl
ebondsar
etr
eat
edasone
bond•VSEPRcanbeappl
iedt
oanyoft
her
esonance
s
truct
ureofamol
ecul
e•s
hapei
sdet
ermi
nedbyt
he

RESONANCE numberofbond pai

rs and l
one pai
rs ar
ound t
he

-us
eoft
woormor
eLewi
sst
ruct
urest
orepr
esenta cent
ralat
om •l
onepai
rsoccupymor
evol
umet
han

par
ticul
armol
ecul
eEx:Oz
one(
O3) bondpai
rs

EXCEPTI
ONSTOOCTETRULE
-r
ulemai
nlyappl
iest
osecondper
iod
-except
ionsf
alli
ntot
hree
I
NCOMPLETEOCTET
Bor
on and Al
umi
num al
so f
orm mol
ecul
es wi
th
Fors
impl
ici
tywewi
llcons
idermol
ecul
est
hatcont
ain
i
ncompl
eteoct
ets
.
at
omsofonl
ytwoel
ement
s-AandB
Ex:BeH2
A=cent
ralat
om B=t
heot
herel
ementbondedt
oA
ODD#OFELECTRON
AB2,AB3,AB4,AB5,andAB6
Ex:
AB2(
LINEAR)
-oddnumber
edmol
ecul
esar
esomet
imesr
efer
redt
o
Ex:BeCl
2(Ber
yll
ium chl
ori
de)
asr
adi
cal
s-gener
all
yhi
ghl
yreact
ive
AB3(
TRI
GONALPLANAR)
EXPANDEDOCTET
Ex:Bor
ont
rif
luor
ide(
BF3)
-at
omsofel
ement
sint
he3r
dper
iodandbeyond-
AB4(
TETRAHEDRAL)
have3dor
bit
alst
hatcanpar
tici
pat
eint
hebondi
ng-
Ex:Met
hane(
CH4)
AB5(
TRI
GONALBI
PYRAMI
DAL)
Ex:Phos
phor
uspent
afl
uor
ide(
PF5)
AB6(
OCTAHEDRAL)
Ex:Sul
furhexaf
luor
ide(
SF6)

MOLECULARGEOMETRY
Formol
ecul
eswhi
ch hasa cent
ralat
om A,ot
her
el
ementB,andoneormor
eloneel
ect
ronpai
rsE.
AB2E(
TRI
GONALPLANAR)
MOLECULARGEOMETRY
Ex:SO2
Formol
ecul
eswi
thmor
ethanonecent
ralat
om:
(
Sul
furdi
oxi
de)
Exampl
e:Et
hanol(
CH3OH)Cent
ralat
oms
:CandO
Recal
l:
1.
Doubl
ebondsar
etr
eat
edass
ingl
ebond
DI
POLEMOMENT&POLARI
TY
2.
Lone pai
r-bondi
ng pai
rrepul
sion gr
eat
er t
han
Pol
ari
tycanbemeas
uredi
nter
msofdi
pol
emoment
,
bondi
ngpai
rvsbondi
ngpai
r
µ
Di
pol
e moment–pr
oductofchar
ge (
Q)and t
he
AB2E(
BENT)
di
stancebet
weenchar
ges(
r)
Ex:SO2
Debye(
D)–uni
tofdi
pol
emoment
;1D=3.
336x10-
30
(
Sul
furdi
oxi
de)
Cm
El
ect
ronor
ient
ati
on:Tr
igonalpl
anarMol
ecul
ar
geomet
ry:Bent Bondangl
e:<120degr
ees
FUNCTI
ONALGROUPS
-gr
oupst
hatar
eres
pons
ibl
eformos
toft
her
eact
ions
AB3E(
TETRAHEDRAL)
oft
hepar
entcompounds
Ex:Ammoni
a(NH3)
ALCOHOLS
AB3E(
PYRAMI
D)
-cont
ains hydr
oxylf
unct
ionalgr
oup,-
OH;mos
tly
Ex:Ammoni
a(NH3)
f
lammabl
e;weakl
yaci
dic
El
ect
ronor
ient
ati
on:Tet
rahedr
al
Met
hanol-s
impl
est(
met
hanol
);hi
ghl
ytoxi
c and
Mol
ecul
argeomet
ry:Pyr
ami
d
caus
esbl
indnes
s
Bondangl
e:107.
3degr
ees
Et
hanol-t
hebes
t-known al
cohol
;fr
om r
eact
ion of
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