Cycloalkanes(naphthenes) have1+ringsofcarbonatoms consistofonlyCandHatoms cycloalkanew/oneringtreatedasisomersoftheiralkenecounterpart(Ex:

cyclopropane/propene)Formula:CnH2(n+1g)wheren=numberofCatomsandg=numberofringsinthemoleculeIUPACnaming:

1. basenamelistedfirst(total#ofCinbothrings)2. numericalprefixbeforebasename(#ofCineachring,ex.sharedC)(Ex:#C1string.#

C2ndring.SharedC)Properties:

higherboiling/meltingpointsthanalkanes higherdensities strongerLDF(morecontactarea)

RingStrain: sp3hybridized PE/destabilizingeffect strainenergy:theoreticalincreaseinenergycausedbythecompoundsgeometry

calculatedbycomparingtheexperimentalstandardenthalpychangeofcombustionhighestforcyclopropane

Reactions: simple&biggercycloalkanesareverystable smallcycloalkanesarelessstableBaeyerstrain/ringstrain

Alkenes(olefin,olefine)

unsaturatedhydrocarbonsthatcontain1+C=C simplestalkeneethylene(C2H4)producedonthelargestscaleindustrially

Formula:acyclicalkenes(monoenes)formahomologousseriesofhydrocarbonsCnH2nIUPACnaming:antoene

1. #thelongestCchainthatcontains=inthedirectionthatgivestheCatomsofthe=thelowestpossible#s

2. Indicatethelocationofthe=bythelocationofits1stC3. Namebranched/substitutedalkenes4. #theCatoms,locate/namesubstituents,locate=,namemainchain

CistransnotationCisusedifbothsubstituentsareonthesamesideofthebond Transusedifsubstituentsareoneithersideofthebond

Properties: colorless,nonpolar,combustible,almostodorless simplestalkenesaregaseswherethecomplicatedonesarewaxysolids

Bonding: eachCofthe=usesitsthreesphybridorbitalstoformsigmabondstothreeatoms =about120,butvariesbcofstericstrainintroducedbynonbondedinteractionscreated

byfunctionalgroupsattachedtotheCofthe=Reactions:

relativelystable,butmorereactivethanalkanesbcofreactivityofpibond reactionsinvolve:additionstopibond,hydrogenation,hydration,halogenation,

hydrohalogenation,halohydrinformation,oxidation,photooxygenation,polymerization,metalcomplexation

Synthesis: Industrialmethods:producedbyhydrocarboncracking(alkanesbreakingapartathigh

temps) Eliminationreactions:morereliableeliminationmethodthanE1formostalkene

syntheses.MostE2eliminationsstartwithanalkylhalide(dehydrohalogenation)oralkylsulfonateester

Alkynes

unsaturatedhydrocarbonw/1+carboncarbontriplebondFormula:CnH2n2IUPACnaming:ethyneChemicalproperties:

moreunsaturated&lessreactivethanalkenes greatertendencytopolymerize

Structure&Bonding: 180rodlike BenzyneUNSTABLE strongbonds

Synthesis: usedasafuel&precursortoothercompounds Propynethermalcrackingofhydrocarbons

Reactions: additionofhydrogen,halogens,andrelatedreagents cycloadditions&oxidation reactionsspecificforterminalalkynes

AlkylHalides(Haloalkanes)

derivedfromalkanescontaining1+halogens usedasflameretardants,fireextinguishants,refrigerants,propellants,solvents,

pharmaceuticals

seriouspollutant(ozonedepletion,fumigant)IUPACnaming:halogenasaprefixtoalkaneProperties:

colorless,odorless,hydrophobic higherboilingpointsthanalkanes(highIMF) bettersolvents haloalkanescont.halogensotherthanFaremorereactive

Occurence: pharmaceuticalscontainF perfluorinatedalkanesarebloodsub.

Production: freeradicalhalogenation reactswithdryHhalide tertiaryalcoholreactsw/HCLtomaketertiarychloroalkane Hunsdiecherreaction/Kochireaction

Alcohols

anyorganiccompoundinwhichtheOHisboundtoasaturatedCatomFormula:CnH2n+1OHIUPACnaming:

nameofalkanechainloseseandaddsol(positionofOHgroupcanbeindicatedby#b/talkanename&ol)

ifhigherprioritygroupispresent(aldehyde,ketone,carboxylicacid),thenhydroxyusedToxicity:

ethanolstoxicitycausedbymetabolite,acetaldehyde&aceticacid tertiaryalcoholscannotbemetabolizednotoxicity treatment:admin.ethanol

Phys./Chem.Properties: odor hydroxylgroupmakeitpolar canbeusedasproticsolvents higherboilingpoint canundergooxidationornucleophilicsub.reactions

App.: alcoholicbeverages antifreeze antiseptics fuels preservatives

solventsProduction:

Ziegler&Oxoprocesses hydrationreactions biologicalroutes

LabSynthesis: substitution reduction hydrolysis

Thiols(mercaptan)

organosulfurcompoundthatcontainsaCbondedsulfhydryl(CSHorRSH) sulfurtakesplaceofOinhydroxylgroupofalcohol

IUPACnaming: thioladdedtonameofalkane mercaptanreplacesalcohol sulfanyl.mercaptousedasprefix

Structure/Bonding sizeofchalcogenidediffers CSHanglesalmost90 lesspolarthanhydroxylgroup

PhysicalProp: garlicodor lowerboilingpt lesssolubleinwaterthanalcohols

Characterization: detectedbyodor

Prep: reactionofhydrogensulfidew/methanol synthesisofmethanethiol

Reactions: Salkylation Acidity Redox

Biologicalimportance: cysteine/cystine cofactors(nonproteinbasedhelpermolecules)

Ethers containethergroup

SymbolRORIUPACnaming:

alkoxyalkane ifetherisapartofmorecomplexmoleculemethoxy

Structure/Bonding: COClinkageofabout104 sp3

Trivialnames: simpleetherscompositeof2substituentsfollowedbyether

Phys.Prop.: nohydrogenbonds lowboilingpoint(becomelowerasCchaingetslonger) slightlypolar lowerethersarehighlyvolatile

Reactions: ethercleavage peroxideformation Lewisbases Alphahalogenation

Epoxides cyclicetherwitha3atomring highlystrained

IUPACnaming:epoxySynthesis:

olefinperoxidation intramolecularSN2substitution nucleophilicepoxidation asymmetricepoxidation

Reactions: Nucleophilicaddition Hydrolysis Reductionofanepoxidew/lithiumaluminumhydrideandwatergen.analcohol Reductionw/tungstenhexachlorideandnbutyllithiumgen.thealkene

Aldehyde

organiccompoundw/formylgroup(functionalgroupw/RCHOstructure) aldehydegroup:groupw/oR

IUPACnaming:1. Acyclicaliphaticaldehydesarenamedasderivativesofthelongestcarbonchain

containingthealdehydegroup.Thus,HCHOisnamedasaderivativeofmethane,

andCH3CH2CH2CHOisnamedasaderivativeofbutane.Thenameisformedby

changingthesuffixeoftheparentalkanetoal,sothatHCHOisnamed

methanal,andCH3CH2CH2CHOisnamedbutanal.

2. whenaCHOgroupisattachedtoaring,thesuffixcarbaldehydemaybeused.

Thus,C6H11CHOisknownascyclohexanecarbaldehyde.Ifthepresenceof

anotherfunctionalgroupdemandstheuseofasuffix,thealdehydegroupis

namedwiththeprefixformyl.Thisprefixispreferredtomethanoyl.

3. Ifthecompoundisanaturalproductoracarboxylicacid,theprefixoxomaybe

usedtoindicatewhichcarbonatomispartofthealdehydegroupforexample,

CHOCH2COOHisnamed3oxopropanoicacid.

4. Ifreplacingthealdehydegroupwithacarboxylgroup(COOH)wouldyielda

carboxylicacidwithatrivialname,thealdehydemaybenamedbyreplacingthe

suffixicacidoroicacidinthistrivialnamebyaldehyde.

Structure/Bonding:

sp2hybridized,planarcarboncenterconnectedby=toOandatoH

PhysProp&Characterization:

smalleraldehydesmoresolubleinH2O

volatilealdehydeshavepungentodors

IDedbyspectroscopicmethods

formaldehyde/acetaldehyde

App.&Occurence:

foundinessentialoils&odors(cinnamaldehyde,cilantro,vanillin)

Synthesis:

oxidativeroutes(alcoholoxidation)

Specialtymethods(ozonolysis,organicreduc,rosenmundreaction,wittigreaction,

formylationreactions,nefreaction,zinckereaction,etc)

CommonReactions:

reduction/oxidation

nucleophilicadditionreactions

oxygen/nitrogen/carbonnucleophiles

bisulphitereaction

Ketones

organiccompoundwithstructureRC(=O)RwhereRandRcanbeavarietyof

Ccontainingsubstituents

simplecompoundsw/acarbonylgroup(C=O)simplebctheydonthavereactive

groupslikeOHorClattacheddirectly

IUPACnaming:

anetoanone

acetone/benzophenone

oxoistheIUPACnameforaketonefunctionalgroup

Structure/Properties:

sp2hybridized

trigonalplanar,120

polar

nucleophilicatO/electrophilicatC

Classes:diketones,unsaturatedketones,cyclicketones

Characterization:

Hatomattachedtoitscarbonylgroup=easiertooxidize

absorbstronglyintheinfraredspectrumnear17001/cm

Synthesis:

oxidationofhydrocarbons

preparedbyoxidationofsecondaryalcohols

Reactions:

Withwater(hydration)givesgeminaldiols

Withanacetylidetogivethehydroxyalkyne

Withammoniaoraprimaryaminegivesanimine

Withsecondaryaminegivesanenamine

WithGrignardandorganolithiumreagentstogive,afteraqueousworkup,atertiary

alcohol

Withanalcoholsoralkoxidestogivesthehemiketaloritsconjugatebase.Withadiolto

theketal.

WithsodiumamideresultinginCCbondcleavagewithformationoftheamide

RCONH2andthealkaneR'H,areactioncalledtheHallerBauerreaction.

Withstrongoxidizingagentstogivecarboxylicacids.

Electrophilicaddition,reactionwithanelectrophilegivesaresonancestabilizedcation

WithphosphoniumylidesintheWittigreactiontogivethealkenes

Withthiolstogivethethioacetal

Withhydrazineor1disubstitutedderivativesofhydrazinetogivehydrazones.

Withametalhydridegivesametalalkoxidesalt,hydrolysisofwhichgivesthealcohol,

anexampleofketonereduction

Withhalogenstoformanhaloketone,areactionthatproceedsviaanenol(see

Haloformreaction)

Withheavywatertogiveandeuteratedketone

FragmentationinphotochemicalNorrishreaction

Reactionof1,4aminodiketonestooxazolesbydehydrationintheRobinsonGabriel

synthesis

Inthecaseofarylalkylketones,withsulfurandanaminegiveamidesintheWillgerodt

reaction

Withhydroxylaminetoproduceoximes

Withreducingagentstoformsecondaryalcohols

WithperoxyacidstoformestersintheBaeyerVilligeroxidation

Biochemistry:

formationoforganiccompoundsinphotosynthesisoccursviatheketone

ribulose1,5biphosphate

fructose

ketonebodies:acetone,acetoacetate,betahydroxybutyrate

Applications:

solvents,polymerprecursors,pharmaceuticals

Esters

chemicalcompoundsrevivedfromanacidinwhich1+OHgroupisreplacedbyan

Oalkylgroup

derivedfromacarboxylicacid&analcohol

Formula:R,ORsinglebondedtoC&OdoublebondedtoC

IUPACnaming:

oate

RCO2RwhereRandRarethehydrocarbonpartsofthecarboxylicacid/alcohol

Structure/Bonding:

containacarbonylcenter,120CCO&OCOangles

flexiblefunctionalgroupslessrigid(lowermeltingpoint)&morevolatile(lowerboiling

point)thanthecorrespondingamides

pKaaround25

Phys.Properties:

morepolarthanethersbutlesspolarthanalcohols

participateinhydrogenbondsashydrogenbondacceptors(notdonors!)

volatile

Apps&Occurrence:

responsibleforaromaofmanyfruits

polyesters

Preparation:

Esterificationchemicalreactioninwhich2reactants(alcohol/acid)formanesterasthe

reactionproduct

alcoholysis

alkylationofcarboxylatesalts

Esterodorants:

allylhexanoate(pineapple),benzylacetate(strawberry),butylacetate(apple),etc

CarboxylicAcids

organiccompoundthatcontainsacarboxylgroup(C(O)OH)

RC(O)OHwithRreferringtotherestofthemolecule

salts/estersofcarboxylicacidscalledcarboxylates

IUPACnaming:

PhysProperties:

polar

hydrogenbonding

dimericpairs

higherboilingptthanH2O(tendencytoformstabiliseddimers)

BronstedLowryacids

strongodor

Characterization:

IDedbyinfraredspectroscopy

Occurrence/Apps:

polymers,pharm.,solvents,foodadditives,aceticacid

Synthesis:

industrialroutes(oxidationofaldehydes&hydrocarbonsw/airusingcobalt&

manganesecatalysts)

labmethods(oxidationofprimaryalcohols)

Reactions:

HellVolhardZelinskyhalogenation

Amines

organiccompounds/functionalgroupsthatcontainabasicNatomw/alonepair

derivativesofammonia

structure:RCONRR

IUPACnaming:

aminooramine

Nshowssubstitutiononthenitrogenatom

PhysProperties:

Hbonding(highboilingptthanphosphines)

somesolubility(decreaseswiththeincreasein#ofCatoms)

chiral

bases

Synthesis:

alkylation

reductiveroutes(hydrogenation)

Reactions:

alkylation,acylation,sulfonation

diazotization

conversiontoimines

Biologicalactivity:

breakdownofaminoacidsreleasesamines

neurotransmitters

Applications:

dyes,drugs,gastreatment

Amides(acidamide)

compoundw/functionalgroup

referstoCBofammonia

formula:RnE(O)xNR'2

IUPACnaming: addtermamidetothestemoftheparentacidsname

Structure/Bonding: derivativesofammonia RC(O)NH2 secondaryamines

Properties: veryweakbases lesssolublethancomparableamines/carboxylicacids

Characterization: IRspectra16501/cm

App/Occurrence: nylonsarepolyamides peptidebonds proteins(hairsilk)

Reactions: dehydration,Hofmannrearrangement,amidereduction,VilsmeierHaackreaction

Aromaticity

describesanunusuallystablenatureofsomeflatringsofatomsusuallyw/=

Theory:Theuseofadoubleheadedarrowindicatesthattwostructuresarenotdistinctentities

butmerelyhypotheticalpossibilities.AC=CbondisshorterthanaCCbond,butbenzeneis

perfectlyhexagonalallsixcarboncarbonbondshavethesamelength,intermediatebetween

thatofasingleandthatofadoublebond.Abetterrepresentationisthatofthecircularbond

(Armstrong'sinnercycle),inwhichtheelectrondensityisevenlydistributedthroughabond

aboveandbelowthering.Thismodelmorecorrectlyrepresentsthelocationofelectrondensity

withinthearomaticring.

Characteristics:

delocalizedconjugatedpisystem,mostcommonlyanarrangementofalt./=

coplanarstructure

contributingatomsarrangedin1+rings

#ofpidelocalizede

Importance:

20basicbuildingblocksofproteins

Types:

neutralhomocyclics,heterocyclics,polycyclics,sub.aromatics,atypicalaromatic

compounds