ORGANIC CHEMISTRY CHAPTER 2

Organicstructures
Learnthediagramsusedinfuture
Aim whyweusetheseparticulardiagrams
Howtoname
moleculesinwritingandinspeech
whatistheskeletonofanorganic
molecule
Functionalgroup
Abbreviations
Drawingorganicmoleculesrealistically

andfunctionalgroups
Hydrocarbonframeworks

organicchemistryisthestudy ofcompoundsthatcontaincarbon

iscarbon incarbon cacarbon achainofatoms cringsincluded

chainisbranched1
t

callatomsinasingle
chain chain ringby
forms itself
Aminoacids
allsoluableinwater ay
sharesimilarproperties allbothacidicandbasiccamphoteric
IcanjoinwithotheraAsforformingprotein
Theorganiccompounds chemistrydependsmuchlessonnumbersorarrangementof Cor H Moreontheothertypesofatoms
suchas 0 n s p si
I
of of
Functionalgroupsparts themoleculescontainsmallcollation theseatoms
t
anartscontainafunctionalgroups anaminoinHrorNitgroup
acarboxylicacidgroup
organicskeletons
chainsand
of
rings carbonatomsinmolecules
crudeoil literallycarbonskeletons
Nofunctionalgroups
coal containslittleelsebutcarbon
themoleculesincoalandoildifferwidelyinchemistrystructurehere
Although
onethingincommonno Groups
Functional

areveryunreactive
Many

BERealisticEconomicalandCLEAR
Drawingmolecules
zizig
Guideline l Drawchainsofatomsaszigzags

linoleicacid
Atattyacidcannotbesynthesizedinthehumanbody
but
must beancomponentofahealthydiet
found
out
Guideline2Miss theHsattachedtocarbonatomsalongwiththeCHbondsunlessthere is agoodreasonnotto
3 outthecapitalCsrepresentingcarbonatoms1unlessthere'sagoodreasonnotto
Guideline Miss
 Thenewversionofdrawinglinoleicacidisshownbelow

o whenthecarbonatomisnotpartofadoublebond
Theangleofthezigzagsisabouttgo

go
Tetrahedralanger to di
Ib
1090

1200whenit ispart
ofthedoublebond
ywo
c c

structuraldiagramscanbemodifiedtosuit theoccation
Forexample AAscanartasacidorbase
when itactsasanacid abaseremovesHt
fromcarboxylicacidgroupin a reaction
Mtv
fit foot 1 00 two Both t 0 areokay
leucine

whenitactsas abasetheaminoIN
Hisgroupisinvolved
H H
l a H Oit
H n
H l H
N
6TH W cony Huo Alonepairis apairofelectronsthatisnotinvolved
at inachemicalbond
Also not
haslonepairbut
relevantso draw
don't

threedimensionalinformationontwo dimensionalpage
structuraldiagramscanshow

Mtv mn
k N w p
leucine
r 4 way d cont
About stereochemistryofAAs mostnaturallyoccurringaminoacidsarecs attheircarbonwithcysteinebeing R andglycinenonchiral
frameworks
Hydrocarbon

of
names carbonchains

Rememberthatthesesymbolsandnamescanbe
onlyforterminalchainsofatoms
 carbonrings

phenylgroupCph when a benzeneringisattachedto a

molecule
byonlyoneofitscarbonatoms
war nun
OH H
ph
phenylalanine

Aryllar Anycompoundcontaininga benzeneringor arelatedringsystemisknownas aromatic

Arcanmeananysubstitutedphenylring inotherwordsphenylwithanynumberofhydrogenatomsreplacedby
othergroups
a
9
150 phot YY or HN ArOH
phenol
a
paracetamol
2 4btrichlorophenol
Buckminsterfullerene Cbo

Othercyclorings

LIK T grit som

Hoy
oI h
avid cyclamate
Chrysanthemum grandisol
cyclopropane cyclobutanel cyclohexane

Branches

TheisopropylgroupLipm I i pr ipr Pri

e.g yi
N
YY
Lithiumdiisopropylamideupa
Astrongbase
LiniPra
The n alkyl group forexample n PrmBuforstraightchainalkylgroupsnfornormal
N n Pr
Butylgroups
isobutylgroupCiBu Sevbutylgroup sbutylor 5But
it
r l
Atm
Tt Nti rip
theisobutylgroup
l thesebutylgroup
diisobutylaluminumhydridecruzan i Bu s Buli SBn
reducingreagent
antiBu
tertbutylgroup ltbutylortB.nl

yykIBhqyjtBn if
He tertbutylgroup
the
BHT tBu
anantioxidant
 primarysecondaryand
tertiary
A atomisattachedtoonlyoneotherCatom asecondarytoothertwocatomsandSoon
carbon
primary

of
Thereare btypes carbonatoms

methylinoattachedc Primary secondary

µ loneattached c twoattachedC
Me OH 1
methanol on Wtop
butan l ol butan 2 01
n butanol seebutanol

tertiary quaternary
battauhedl 4attachedC
It
Xor Xeon
2 methypropan 201 2 2dimethylpropan101
tertbutanol
ORGANIC CHEMISTRY CHAPTER 2

Functional groups
Alkanescontainnofunctionalgroups
extremelyunreactive
L.mn rr
beusedassolventsuchaspentaneandhexane
could
alkenes sometimescaned
olefinscontain cdoublebonds
cdoublebondsimpartreactivitytoanorganicmolecule
coloredorganiccompoundsoftencontainchainsorrings
of a c
alkynescontain c ctriple bonds

saturatedandunsaturated
atomsattachedtofour
Ingeneralcarbon otheratomsaresaturated
thoseattachedtothreetwooroneareunsaturated
CR containahydroxylcorngroup
Alcohols
on
contain
molecules
torn
oftensolubleinwater
Ethers crio r4containanoak
oxygroupcor
Etheranycompoundhas two alkyi linked
groups throughanoxygenatom
Aminesormancontain the cmin
a mino group
Basic
Formedasmeat decays
Nitrocompoundsornow groupinon
thenitro
contain
nitro
several groupinone can
molecule makeitquiteunstableandevenexplosive
n
n 00 Me
ow no me
nitro
the group Ey n
o L
nor I
TNT nitrazepam
is pin
leering
explosive

halides
alkyl fluoridesRFchlorides r u bromidesRBr oriodidesr IIcontainthe
fluorochlorobromooriodo
groups
fourhave propertiesalkyl
these similar iodides the
are most andalkyl
reactive areleast
fluorides
alsoknownasnaval
Kanes cnn.ro alkanesor
alkaneschiotomicanesbromo iodoakanes

crewand crewrn
aldehydes ketones contain carbonyl group o
o beformed oxidizingalcohols
can
aldehydes by
yaio µ
represents

acids contcontainthecarboxyl
carboxylic cr group cont
canr eact baseslosingaprotonto
with formcarboxylatesalts
Esterser comecontainacarboxylgroupwithanextraalkylgroupcw.rs
Fatareesterssaturatedfat Rgroupsaresaturatedcno c
unsaturated
fat rgroupscontainc c
Amidescrcomn riconureorr con rare
amidesformed
are
proteins betweencarboxylic groupofanother anamide
acidgroupofoneaminoacidwiththeamino linkages

Nitritesorcyanidescrew containthecyanogroup w
beintroducedintomoleculesbyrentingpotassiumcyanidewithalkanehalides
nitrilegroupscan
achlorides rwa
Acylchloridescan
o Too tobe
active foundinnature
11
me a
chloride
acetyl
acetals Roi or
anacetal
Carbonatoms carryingfunctionalgroupscanbeclassified oxidation level
by
Thecarboxylicoxidationlevel 3bonds

Rion R OR R wHv R EN R a
acids
carboxylic esters amides nitriles acylchlorides
beeasilyconvertedintonitriles
Amidescan bydehydration removalofwater sotheyaresameoxidationlevel
Thecarbonatomhas 3bondstoneteroatomsandoniyonetocorri
TanatomthatisnotCorti
leveldetermined
oxidation bythenumberofhetero
atomsbondedtocarbon
oxidationstatedetermined
bythenumberofbondsoncarbon inaudingthosetocandH
Inallthesecompoundscarbonhasfourbondsandisinoxidationstate14
Thealdehydeoxidationlevel12bonds
012
k 14 Riders Roy Uncle
aldehydes ketones
R2 dichloromethane
Racetals H t
Contains acarbon twobonds
atomwith toheteroatom
Thealcoholoxidationlevel cibond
Kray R o R2 Kru R Br
alcohols ethers alkylhalides
contains acarbonatomswithonlyonebondto aheteroatom
fromalcoholswithoutoxidationorreduction
Alleasilymade
Thealkaneoxidationleveltobond
Hugh
H
methane
H
wobondtoheteroatoms
Thecarbondioxideoxidationlevelcabonds
i u a F
c c c c it
Eto ret ai a ai a
y carbontetrachloride CFC au
carbon diethylcarbonate gg yy
dioxide usetuteagentfor formerlyusedasa theaerosolpropellants
oneof
addingestergroups drydeaningfinia totheozonelayer En
causingdamage

summary
ORGANIC CHEMISTRY CHAPTER 2
Namingcompounds
Epseth
systematic nomenclature
describesthehydrocarbon
framework
systematicnamescanbedividedinto3Parts describes functional
the group
indicateswherethefunctionalgroupattachedtotheskeleton

Names forthehydrocarbonframework

NameoffunctionalgroupsThename
Has Fass ofafunctionalgroupcanbeaddedtothenameofhydrocarbonframework
eitherasasuffixor as aprefix
countallofthecarbonatomsinthechainevenifoneofthemispartof afunctionalgroup

Buon
c
Ey
do
To benzene

functionalgroupattachedto a benzene
ringisnamedsimilarly
Numbersareusedtolocate
functionalgroups
whennumbersareusedthecarbonatomsarecountedfromoneend
Inmostcases bothendscouldbeusedforcountingtheonechosen isalwaystheloweroneoftwo
Functionalgroupnamescouldbesuffixor prefixthenumber
alwaysgoesdirectlybeforetheFGnames

Formorethanonefunctionalgroups
 Forcycliccompoundswithoutends usenumberstoshowthedistancebetweentwogroups Istartfromthe C
carryingoneoftheFG Thisrulealsoworksforchainsor ringswithbranchedskeleton

ioftenabbreviatedasomandpi
orthometaand
para
workswithbenzenerings

for
thomeanstwogroupsarenexttoeachotheronthe ringeventhoughtheatomsmaynothappentobenumbered1and

whatdochemistsreallycallcompounds
Namesforwellknownandwidelyusedsimplecompounds
REMEMBER They'recommonlyusedinIab

chemistsusespecial
name forfourfragmentsbecausetheyhavemechanisticaswellasstructuralsignificance

O
f v t I
quitereactive
unreactivetypically
oftenreactive
fairly
fairlyunreactive

namesforcomplicatedbutstillwellknownmolecules

poison

TNT
 compoundsnamed as acronymsk1347347Bog

forwhichchemistsusesystematicnames
compounds

Hath
tellsyoutheframeworksize
thesenamescontain asyllablethat
PentaforCs octaforCsrnona forCgundeeaforcmanddo decaforGv

Howshouldyounamecompounds
structurefirstandworryaboutthenameafterwards
sixpointsinorderofimportance Drawa
Learnthenamesofthefunctional groupscesternitrile etcI
Learnanduse thenamesofafewsimplecompoundsusedbyallchemists
Inspeechrefertocompoundsas thatacid eorwhatever1whilepointingtoa diagram
Grasptheprinciplesofsystematicnomenclatureanduseitformediumsizecompounds
keepanotebooktorecordacronymstrivialnames structuresetcthatyoumayneedlater

Importantstructurestolearn