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Organic and Biological Organic and Biological MoleculesMolecules

Chapter 22Chapter 22

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Organic Chemistry and BiochemistryOrganic Chemistry and Biochemistry

The study of carbon-containing The study of carbon-containing compounds and their properties.compounds and their properties.The vast majority of organic The vast majority of organic compounds contain chains or rings compounds contain chains or rings of carbon atoms.of carbon atoms.The study of the chemistry of living The study of the chemistry of living mattermatter

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HydrocarbonsHydrocarbons compounds composed of carbon and compounds composed of carbon and

hydrogen.hydrogen. SaturatedSaturated compounds (alkanes) have compounds (alkanes) have

the maximum number of the maximum number of hydrogen hydrogen atomsatoms attached to each carbon atom attached to each carbon atom

H C

H

H

C

H

H

H

4

UnsaturatedUnsaturated compounds have compounds have fewer hydrogen atoms attached fewer hydrogen atoms attached to the carbon chain than alkanesto the carbon chain than alkanes

Unsaturated:Unsaturated: They They contain contain carbon-carbon multiple bonds carbon-carbon multiple bonds (double or triple)(double or triple)

H C

H

H

C

H

CH

H

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22.1 Alkanes: Saturated hydrocarbons22.1 Alkanes: Saturated hydrocarbons

Saturated hydrocarbons, Saturated hydrocarbons, CCnnHH2n+22n+2 ““Saturated” because they Saturated” because they can’t takecan’t take any more any more

hydrogen atoms hydrogen atoms Normal straight chains Normal straight chains (unbranched hydrocarbons)(unbranched hydrocarbons) HH33C–(CHC–(CH22))n–2n–2–CH–CH33

Waxes, oils, & fuel gases as n decreases.Waxes, oils, & fuel gases as n decreases.

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Alkanes: Saturated HydrocarbonsThe C-H Bonds in Methane

7

The Lewis structure of ethaneThe Lewis structure of ethane..

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PropanePropane

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ButaneButane

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The First 10 “Normal” AlkanesThe First 10 “Normal” AlkanesNameName FormulaFormula M.P.M.P. B.P.B.P. # Structural Isomers# Structural Isomers

MethaneMethane CHCH44 -183-183 -162-162 11 EthaneEthane CC22HH66 -172-172 -89-89 11 PropanePropane CC33HH88 -187-187 -42-42 11 ButaneButane CC44HH1010 -138-138 0 0 22 PentanePentane CC55HH1212 -130-130 36 36 33 HexaneHexane CC66HH1414 -95-95 68 68 55 HeptaneHeptane CC77HH1616 -91-91 98 98 99 OctaneOctane CC88HH1818 -57-57 126126 1818 NonaneNonane CC99HH2020 -54-54 151151 3535 DecaneDecane CC1010HH2222 -30-30 174174 7575

C1 - C4 are Gases C1 - C4 are Gases at Room Temperatureat Room Temperature

C5 - C16 are Liquids C5 - C16 are Liquids at Room Temperatureat Room Temperature

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IUPAC Rules for Naming Branched AlkanesIUPAC Rules for Naming Branched Alkanes• Find and name the Find and name the parent chainparent chain in the hydrocarbon - in the hydrocarbon -

this forms the this forms the root of the hydrocarbonroot of the hydrocarbon name name• Number the carbon atoms in the parent chainNumber the carbon atoms in the parent chain

starting at the end closest to the branchingstarting at the end closest to the branching• NameName alkane branchesalkane branches by dropping the “ane” from by dropping the “ane” from

the names and adding “yl”. A one-carbon branch is the names and adding “yl”. A one-carbon branch is called “methyl”, a two-carbon branch is “ethyl”, called “methyl”, a two-carbon branch is “ethyl”, etc…etc…

• When there are more than one type of branch (ethyl When there are more than one type of branch (ethyl and methyl, for example), they are named and methyl, for example), they are named alphabeticallyalphabetically

• Finally, Finally, use prefixes to indicate multiple branches to indicate multiple branches

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Rules for Naming AlkanesRules for Naming Alkanes

1. 1. For alkanes beyond butane, add For alkanes beyond butane, add -ane-ane to the Greek root for the number of to the Greek root for the number of carbons.carbons.

C-C-C-C-C-C : hexC-C-C-C-C-C : hexaneane2.2. Alkyl substituents: drop the Alkyl substituents: drop the -ane-ane and and

add add -yl-yl -C-C22HH55 is eth is ethylyl

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Rules for Naming AlkanesRules for Naming Alkanes33.. Positions of substituent groups are Positions of substituent groups are

specified by numbering the longest chain specified by numbering the longest chain sequentially.sequentially.

CC C-C-C-C-C-CC-C-C-C-C-C

3-methylhexane3-methylhexane Start numbering at the end closest to the Start numbering at the end closest to the

branchingbranching4.4. Location and name are followed Location and name are followed

by by root alkane nameroot alkane name. Substituents . Substituents are given in alphabetical order and are given in alphabetical order and use di-, tri-, etc.use di-, tri-, etc.

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Normal vs Branched AlkanesNormal vs Branched Alkanes

Normal Normal alkanes consist of alkanes consist of continuouscontinuous chains of chains of carbon atomscarbon atoms

Alkanes that are NOT Alkanes that are NOT continuous chains of continuous chains of carbon atoms contain carbon atoms contain branchesbranches

The longest continuous The longest continuous chain of carbons is called chain of carbons is called the the parent chainparent chain

CH3

CH2CH2

CH2CH3

CH3

CH2CH

CH3

CH3

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Structural IsomerismStructural Isomerism

Structural isomersStructural isomers are are molecules with the same molecules with the same chemical formulas but chemical formulas but different molecular different molecular structures - different structures - different ““connectivity”.connectivity”.

They arise because of the They arise because of the many ways to create many ways to create branched hydrocarbons.branched hydrocarbons.

CH3

CH2CH2

CH2CH3

CH3

CH2CH

CH3

CH3

n-pentane, C5H12

2-methlbutane, C5H12

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Example : Show the structural formula Example : Show the structural formula of 2,2-dimethylpentane of 2,2-dimethylpentane

The parent chain is The parent chain is indicated by the ROOT of indicated by the ROOT of the name - “the name - “pentanepentane”. This ”. This means there are 5 carbons means there are 5 carbons in the parent chainin the parent chain..

CH3

CH2CH2

CH2CH3

• “dimethyldimethyl” tells us that there are TWO methyl branches on the parent chain. A methyl branch is made of a single carbon atom.

• “2,22,2-” tell us that BOTH methyl branches are on the second carbon atom in the parent chain.

CH31

CCH23

CH24

CH35

CH3

CH3

1

2

3

4

5

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Example: Structural formula of Example: Structural formula of 3-ethyl-2,4-dimethylheptane3-ethyl-2,4-dimethylheptane??

The parent chain is The parent chain is indicated by the ROOT of indicated by the ROOT of the name - “the name - “heptaneheptane”. ”. This means there are 7 This means there are 7 carbons in the parent carbons in the parent chain.chain.

CH3

CH2CH2

CH2CH2

CH2CH3

• “2,4-dimethyl2,4-dimethyl” tells us there are TWO methyl branches on the parent chain, at carbons #2 and #4.

• “3-ethyl3-ethyl-” tell us there is an ethyl branch (2-carbon branch) on carbon #3 of the parent chain.

1

2

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5

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CH3

CHCH

CHCH2

CH2CH3

CH2CH3

CH3 CH3

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Example: 2,3,3-trimethyl-4-propyloctaneExample: 2,3,3-trimethyl-4-propyloctane

The parent chain is indicated The parent chain is indicated by the ROOT of the name - by the ROOT of the name - ““octaneoctane”. This means there ”. This means there are 8 carbons in the parent are 8 carbons in the parent chain.chain.

• “2,3,3-trimethyl2,3,3-trimethyl” tells us there are THREE methyl branches - one on carbon #2 and two on carbon #3.

• “4-propyl4-propyl-” tell us there is a propyl branch (3-carbon branch) on carbon #4 of the parent chain.

1

2

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5

7

6

8

1

23

45

7

6

8

CHC

CHCH2

CH2

CH2CH3

CH3

CH3

CH3

CH3CH2

CH2

CH3

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Example : Name the molecules shownExample : Name the molecules shown

parent chain has 5 carbons - parent chain has 5 carbons - “pentane”“pentane”

two methyl branches - start two methyl branches - start counting from the right - #2 counting from the right - #2 and #3and #3

2,3-dimethylpentane2,3-dimethylpentane

CH3

CH2CH

CHCH3

CH3

CH3

parent chain has 8 carbons - parent chain has 8 carbons - “octane”“octane”

two methyl branches - start two methyl branches - start counting from the left - #3 counting from the left - #3 and #4and #4

one ethyl branch - #5one ethyl branch - #5 name branches alphabeticallyname branches alphabetically3,4-dimethyl3,4-dimethyl

4433

octaneoctane

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5-ethyl-5-ethyl-

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Reactions of alkanesReactions of alkanes

Combustion reactionsCombustion reactions2C2C44HH10 10 + 13 O+ 13 O22 8CO 8CO22 + 10 + 10

HH22O(g)O(g) Substitution ReactionsSubstitution Reactions CH4 + Cl2 CH3Cl + HCl

CH3Cl + Cl2 CH2Cl2 + HCl

CH2Cl2 + Cl2 CH Cl3 + HCl

CHCl3 + Cl2 C Cl4

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Dehydrogenation ReactionsDehydrogenation Reactions

CHCH33CHCH33 CH CH22 CHCH22 Ethylene

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Cyclic alkanesCyclic alkanesCCnnHH2n2n

A cycloalkane is made of a hydrocarbon A cycloalkane is made of a hydrocarbon chain that has been joined to make a “ring”.chain that has been joined to make a “ring”.

CH3

CH2CH3 CH2

CH2

CH2

n-propaneC3H8

cyclopropaneC3H6

60° bond angleunstable!!

109.5° bond angle

•Note that two hydrogen atoms were lost in forming the ring

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Ring StructuresRing Structures

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Cyclohexane - Boat & Chair ConformationsCyclohexane - Boat & Chair Conformations Cyclohexane is NOT a planar molecule. Cyclohexane is NOT a planar molecule. To achieve To achieve

its 109.5° bond angles and reduce angle strainits 109.5° bond angles and reduce angle strain, it , it adopts several different conformations. adopts several different conformations.

The The BOATBOAT and and CHAIRCHAIR (99%) are two conformations (99%) are two conformations

Boat

chair

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22.2 Alkenes and Alkynes22.2 Alkenes and Alkynes

AlkenesAlkenes: : hydrocarbons that contain a hydrocarbons that contain a carbon-carbon double bond. carbon-carbon double bond. [CnH2n]

C=CC=C EtheneEtheneCC=CCC=C propenepropene

Alkynes: : hydrocarbons containing a hydrocarbons containing a carbon-carbon triple bond. carbon-carbon triple bond. [CnH2n-2]

C C ΞΞCC EthyneEthyneCCC CCC ΞΞ CC CC 2-pentyne 2-pentyne

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Alkenes & AlkynesAlkenes & Alkynes

Alkenes are Alkenes are hydrocarbons that hydrocarbons that contain at least contain at least one carbon-carbon one carbon-carbon doubledouble bondbond

Alkynes are Alkynes are hydrocarbons that hydrocarbons that contain at least contain at least one carbon-carbon one carbon-carbon triple bondtriple bond

The suffix for the The suffix for the parent alkane chains parent alkane chains are changed from are changed from “ane”“ane” to to “ene”“ene” and and “yne”“yne” e.g. e.g. ethene, ethyneethene, ethyne

Where it is ambiguous, Where it is ambiguous, the BONDS are the BONDS are numbered like numbered like branches so that branches so that the the location of the multiple location of the multiple bond may be indicatedbond may be indicated

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AlkAlkeenes, Cnes, CnnHH2n2n

Cycle formation isn’t the only possible Cycle formation isn’t the only possible result of result of dehydrogenation.dehydrogenation.

Adjacent C’s can double bond, C=C, Adjacent C’s can double bond, C=C, making an (unsaturated) alkmaking an (unsaturated) alkeneene..

Sp2

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Nomenclature for AlkenesNomenclature for Alkenes

1.1. Parent hydrocarbon name ends in Parent hydrocarbon name ends in -ene-ene CC22HH4; 4; CHCH22=CH=CH22 is is etheneethene

2.2.With more than 3 carbons, double bond is With more than 3 carbons, double bond is indicated indicated by the lowest numbered carbonby the lowest numbered carbon atom in the bond.atom in the bond.

C=C-C-C is C=C-C-C is 1-butene1-butene

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Nomenclature alkenes and Nomenclature alkenes and alkynesalkynes

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Cis and Trans IsomersCis and Trans Isomers Double bond is fixed (rotation around the Double bond is fixed (rotation around the

double bond is restricted)double bond is restricted) Cis/trans Isomers are possibleCis/trans Isomers are possible

CHCH33 CH CH33 CH CH33

CH = CHCH = CH CH = CH CH = CH

ciscis transtrans CH CH33

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Reactions of alkenes and alkynesReactions of alkenes and alkynes

in which (weaker) in which (weaker) bonds are bonds are broken and new (stronger) broken and new (stronger) bonds bonds are formed to atoms being added.are formed to atoms being added.

1. Addition ReactionsAddition Reactions

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Hydrogenation reactionHydrogenation reaction

Adds a hydrogen atom to each Adds a hydrogen atom to each carbon atom of a double bondcarbon atom of a double bond

H HH H H H H H catalystcatalyst

H–C=C–H + H–C=C–H + HH2 2 H–C–C–HH–C–C–H

H H H H

Ethene Ethene EthaneEthane

CH3-CH3

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Halogenation reactionHalogenation reaction

Adds a halogen atom to each carbon Adds a halogen atom to each carbon atom of a double bondatom of a double bond

H HH H H H H H catalystcatalyst

H–C=C–H + H–C=C–H + ClCl2 2 H–C–C–HH–C–C–H

Cl Cl Cl Cl

Ethene Dichloro Ethene Dichloro ethaneethane

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Halogenation ReactionsHalogenation Reactions

CH2 CHCH2CH2CH2 + Br2

CH2Br CHBrCH2CH2CH2

1,2-dibromopentane

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Alkynes, Alkynes, CCnnHH2n–22n–2

Carbon-carbon triple bondsCarbon-carbon triple bonds Names end in -Names end in -yneyne

HCHCCHCH ethethyneyne(acet(acetyleneylene))

HCHCC-CHC-CH33 proppropyneyne

•sp triple bonding makes a rigid 180° segment in a hydrocarbon.

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The Bonding in The Bonding in AcetyleneAcetylene

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Naming Alkenes and AlkynesNaming Alkenes and Alkynes

When the carbon chain has 4 or more C atoms, When the carbon chain has 4 or more C atoms, number the chain to give the lowest number to the number the chain to give the lowest number to the double or triple bond.double or triple bond.

1 2 3 41 2 3 4

CHCH22=CHCH=CHCH22CHCH33 1-butene1-butene

CHCH33CH=CHCHCH=CHCH33 2-butene2-butene

CHCH33CHCHCHCHCHCH33 2-butyne2-butyne

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QuestionQuestion

Write the IUPAC name for each of the Write the IUPAC name for each of the following unsaturated compounds:following unsaturated compounds:

A.A. CHCH33CHCH22CCCCHCCH33

CHCH33

B. B. CHCH33C=CHCHC=CHCH33 C. C.

CH32-pentyne

2-methyl-2-butene 3-methylcyclopentene

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QuestionQuestion

Name the following compoundName the following compound

CH3CH2C CCHCH2CH3CH2CH3

CH3CH2C CCHCH2CH3CH2CH3

1 2 3 4 5 6 7

5-ethyl-3-heptyne

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Additions reactions:Hydrogenation and Additions reactions:Hydrogenation and HalogenationHalogenation

Hydrogens and halogens also add to Hydrogens and halogens also add to the triple bond of an alkynethe triple bond of an alkyne..

CH3C CCH2CH3 + Br2 CH3C CCH2CH3

Br Br

Br Br

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22.3 Aromatic hydrocarbons22.3 Aromatic hydrocarbonsUnsaturated Cyclic hydrocarbonsUnsaturated Cyclic hydrocarbons Alternating single/double bondAlternating single/double bond cycles occur in many organic moleculescycles occur in many organic molecules

This class is called This class is called “aromatic”“aromatic” (by (by virtue of their aroma).virtue of their aroma).

• Delocalized bonds possess a great stabilitythus benzene does not react like unsaturated hydrocarbons

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Benzene CBenzene C66HH66

sp2

sp2sp2

The The structure is structure is often preserved in often preserved in benzene chemical benzene chemical reactionsreactions Aromatic rings Aromatic rings do not add, they do not add, they substitute insteadsubstitute instead

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Shorthand notation for benzene ringsShorthand notation for benzene rings

The bonding in the The bonding in the benzene ring is a benzene ring is a combination of different combination of different Lewis structuresLewis structures

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Aromatic HydrocarbonsAromatic Hydrocarbons

Substitution reactionSubstitution reaction

+ Cl2

FeCl3

Cl

+ HCl+H2O+HCl

benzene

Chlorobenzene

HNO3

HNO3

CH3Cl

-NO2

-CH3

Nitroobenzene

Toluene

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Nomenclature of benzene derivativesNomenclature of benzene derivatives

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More Complex Aromatic SystemsMore Complex Aromatic Systems

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22.422.4 Hydrocarbon DerivativesHydrocarbon Derivatives(Functional Groups(Functional Groups))

Molecules that are fundamentally Molecules that are fundamentally hydrocarbons but have additional atoms hydrocarbons but have additional atoms or group of atoms called functional or group of atoms called functional groupsgroups

Part of an organic molecule where Part of an organic molecule where chemical reactions take placechemical reactions take place

Replace an H in the corresponding alkaneReplace an H in the corresponding alkane Provide a way to classify organic Provide a way to classify organic

compoundscompounds

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The Common Functional GroupsThe Common Functional Groups

ClassClass General General FormulaFormula

HalohydrocarbonsHalohydrocarbons RRXX AlcoholsAlcohols RROHOH EthersEthers RROORR AldehydesAldehydes

R CO

H

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ClassClass General General FormulaFormula

KetonesKetones Carboxylic AcidsCarboxylic Acids EstersEsters

AminesAmines

R CO

R'

R CO

OH

R CO

OR'

R NH2

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Some Types of Functional Some Types of Functional GroupsGroups

HaloalkaneHaloalkane -F, -Cl, -Br CH-F, -Cl, -Br CH33ClClAlcoholAlcohol -OH-OH CH CH33OHOH

EtherEther -O--O- CH CH33-O-CH-O-CH33

AldehydeAldehyde

KetoneKetone

C HO

CH3CHO

C

OCH3CCH3

O

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More Functional GroupsMore Functional Groups

Carboxylic acidCarboxylic acid -COOH-COOH CH CH33COOHCOOH

EsterEster -COO--COO- CH CH33COOCHCOOCH33

AmineAmine -NH-NH22 CH CH33NHNH22

AmideAmide -CONH-CONH22 CH CH33CONHCONH22

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HaloahydrocarbonsHaloahydrocarbonsAn alkane in which one or more H An alkane in which one or more H atoms is replaced with a halogen (F, atoms is replaced with a halogen (F, Cl, Br, or I)Cl, Br, or I)

CHCH33BrBr bromomethanebromomethane BrBr (methyl bromide)(methyl bromide)

CHCH33CHCH22CHCHCHCH33 2-bromobutane2-bromobutane ClCl chlorocyclobutanechlorocyclobutane

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Name the following:Name the following:

bromocyclopentanebromocyclopentane

1,3-1,3-dichlorocyclohexanedichlorocyclohexane

Br

Cl

Cl

1 2 3

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SubstituentsSubstituents

List other attached atoms or groups List other attached atoms or groups in alphabetical orderin alphabetical orderBr = bromo, Cl = chloro Br = bromo, Cl = chloro

Cl BrCl Br

CHCH33CHCHCHCH22CHCHCHCH22CHCH22CHCH33

4-bromo-2-chloroheptane4-bromo-2-chloroheptane

1 2 3 4 5

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NomenclatureNomenclature

The name of this compound is:The name of this compound is:ClCl CH CH33

CHCH33CHCH22CHCHCHCH22CHCHCHCH33

4-chloro-2-methylhexane4-chloro-2-methylhexane

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Alcohols: R–OHAlcohols: R–OH The –OH makes alcohol polar enough The –OH makes alcohol polar enough

to to hydrogen bondhydrogen bondinging Thus, they are Thus, they are water solublewater soluble EthanolEthanol is produced by the is produced by the

fermentation of glucosefermentation of glucoseyeastC6H12O6

Glucose2CH3CH2OHEthanol + 2 CO2

CO + 2H2O CH3OH Methanol

• Methanol is produced industrially by hydrogenation of carbon monoxide

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Uses of alcoholsUses of alcohols Methanol is used to synthesize Methanol is used to synthesize

adhesives, fibers, plastics and recently as adhesives, fibers, plastics and recently as motor fuelmotor fuel

It is toxic to human and can leadIt is toxic to human and can lead to to blindness and death blindness and death

Ethanol can be added to gasoline to form Ethanol can be added to gasoline to form gasoholgasohol and used in industry as solvent and used in industry as solvent

Commercial production of ethanol:Commercial production of ethanol: CHCH22=CH=CH22 + H + H22O CHO CH33CHCH22OH OH

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Classes of alcoholsClasses of alcohols

R CH2OH Primary alchol

CHOHR'R

Secondary alcohol

CR'R

R"OH Tertiary alcohol

Alcohols can be classified according to the number of hydrocarbon fragments bonded to number of hydrocarbon fragments bonded to the carbonthe carbon where the –OH group is attached

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Naming AlcoholsNaming Alcohols

In IUPAC name, the In IUPAC name, the -e-e in in alkane alkane name is replaced with name is replaced with -ol-ol..CHCH4 4 methanemethane

CHCH33OH OH methanol methanol (methyl alcohol)(methyl alcohol)

CHCH33CHCH33 ethaneethane

CHCH33CHCH22OH ethanolOH ethanol (ethyl (ethyl alcoholalcohol))

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OH

Phenol(Aromatic alcohol)

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Some Typical AlcoholsSome Typical Alcohols OHOH ““Rubbing alcohol”Rubbing alcohol” CHCH33CHCHCHCH33

2-propanol (isopropyl alcohol)2-propanol (isopropyl alcohol)

Antifreeze Antifreeze HO-CHHO-CH22-CH-CH22-OH-OH1,2-ethanediol1,2-ethanediol (ethylene glycol)(ethylene glycol)

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Naming AlcoholsNaming Alcohols

IUPAC names for longer chains number the IUPAC names for longer chains number the chain from the chain from the end nearest the -OH groupend nearest the -OH group..

CHCH33CHCH22CHCH22OHOH 1-propanol1-propanol

OHOH CHCH33CHCHCHCH33 2-propanol2-propanol

CHCH3 3 OHOH CHCH33CHCHCHCH22CHCH22CHCHCHCH33 5-methyl-2-hexanol5-methyl-2-hexanol

5 2

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Name the following alcohols:Name the following alcohols: OH OH

CHCH33CHCHCHCHCHCH22CHCH33

CHCH33

Example

3-methyl-2-pentanol

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Aldehydes and KetonesAldehydes and Ketones

In an aldehyde, an In an aldehyde, an H atomH atom is attached is attached to a to a carbonyl carbonyl groupgroup

OO carbonyl groupcarbonyl group CHCH33-C--C-HH In a ketone, In a ketone, two carbon groupstwo carbon groups are are

attached to a attached to a carbonylcarbonyl group group OO carbonyl groupcarbonyl group

CHCH33-C--C-CHCH33

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Naming AldehydesNaming Aldehydes IUPAC name: Replace the IUPAC name: Replace the -e-e in the alkane in the alkane

name by name by -al-al Common Add Common Add aldehyde aldehyde to the prefixes to the prefixes form form

(1C), acet (2C), propion(3), and butry(4C)(1C), acet (2C), propion(3), and butry(4C) OO OO OO

H-H-CC-H-H CHCH33-C-C-H-H CHCH33CHCH22CC-H-H

methanalmethanal ethanal ethanal propanal propanal((formaldehyde) (acetaldehyde) formaldehyde) (acetaldehyde)

(propionaldehyde)(propionaldehyde)

methane ethane propane

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Aldehydes as FlavoringsAldehydes as Flavorings

CHO

CHO

HOOCH3

CH=CH CHO

Benzaldehyde Vanillin Cinnamaldehyde(almonds) (vanilla beans) (cinnamon)

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Naming KetonesNaming Ketones IUPAC name: the IUPAC name: the -e-e in the alkane name is in the alkane name is

replaced with replaced with –one–one and a number to indicate and a number to indicate the position of carbonyl group when needed. the position of carbonyl group when needed.

In the common name, add the word In the common name, add the word ketoneketone after naming the alkyl groups attached to the after naming the alkyl groups attached to the

carbonyl groupcarbonyl group OO OO

CHCH33 -C-CH -C-CH33 CH CH33-C-CH-C-CH22-CH-CH33

2-Propanone2-Propanone 2-Butanone2-Butanone (Dimethyl ketone) (Ethyl methyl ketone)(Dimethyl ketone) (Ethyl methyl ketone)

O

CyclohexanoneAcetone

propanebutane

cyclohexane

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Name the following compoundsName the following compounds

OO

A. CHA. CH33CHCH22CCHCCH33 B.B.2-butanone (ethyl methyl ketone) 2-butanone (ethyl methyl ketone)

CHCH3 3 O O

C. CHC. CH33-C-CH-C-CH22CHCH cyclohexanonecyclohexanone CHCH33

3,3-dimethylbutanal3,3-dimethylbutanal

O

72

Draw the structural formulas for each of the following Draw the structural formulas for each of the following

compoundscompounds

CHCH33 OO A. 3-MethylpentanalA. 3-Methylpentanal CHCH33CHCH22CHCHCHCH22CHCH

Br OBr O

B. 2,3-DibromopropanalB. 2,3-Dibromopropanal Br-CH Br-CH22CHCHCHCH

OO

C. 3-Methyl-2-butanoneC. 3-Methyl-2-butanone CHCH33CHCCHCHCCH33

CHCH33

73

Preparation of aldehydes and Preparation of aldehydes and KetonesKetones

They are produced by oxidation of They are produced by oxidation of alcohols:alcohols:

CHCH33CHCH22OOHHOxidation

CH3CHCH3

OH

Oxidation CH3CCH3O

CH3CO

Hacetaldehyde

acetone

Primary alcohol

Secondary alcohol

ethanal

propanone

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Carboxylic Acids and EstersCarboxylic Acids and Esters

Carboxylic acids contain the carboxyl Carboxylic acids contain the carboxyl group as carbon 1.group as carbon 1.

OO R R

CHCH3 3 —— CC——OHOH CHCH33——COOHCOOH

carboxyl groupcarboxyl groupGeneral formula R—General formula R—COOHCOOH

75

Nomenclature of Carboxylic AcidsNomenclature of Carboxylic AcidsFormulaFormula IUPAC IUPAC Common Common

alkan -alkan -oic acidoic acid prefix prefix – ic acid– ic acid

HHCCOOHOOH methanoic acid methanoic acid form formicic acidacidCCHH33CCOOH OOH ethanoic acid ethanoic acid acet aceticic acidacid

CCHH33CCHH22CCOOHOOH propanoic acid propanoic acid propion propionicic acidacid

CCHH33CCHH22CCHH22CCOOH butanoic acid butyrOOH butanoic acid butyricic acidacid

76

IUPAC nomenclature for IUPAC nomenclature for Carboxylic acidsCarboxylic acids

Identify longest chainIdentify longest chain Number Number carboxyl carbon as 1carboxyl carbon as 1 CHCH33

||CHCH3 3 —— CH—CHCH—CH2 2 —COOH—COOH 3-methylbutanoic acid3-methylbutanoic acid

1234

77

CHCH33

|| CHCH33CHCOOHCHCOOH

2-methylpropanoic acid;2-methylpropanoic acid;

78

Reaction of carboxylic acid with alcoholReaction of carboxylic acid with alcohol

CH3CO

OH + H OCH2CH3

CH3CO

OCH2CH3 + H2O

Ester

Carboxylic acid Alcohol

Esterification

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EstersEstersIn ester, theIn ester, the HH in the in the carboxyl groupcarboxyl group is is

replacedreplaced with an with an alkyl groupalkyl group

OO

CHCH3 3 —— C—OC—O —CH—CH33 CHCH33——COOCOO ——CHCH33

ester groupester group

•Esters give fruity odors

80

Naming Esters

• The parent alcohol is named first with a –yl ending

• Change the –oic ending of the parent acid to –ate

acid alcohol O methylCH3 — C—O —CH3

Ethanoate methyl ethanoate (IUPAC)(acetate) methyl acetate (common)

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AminesAmines Organic compounds of nitrogen N; Organic compounds of nitrogen N;

derivatives of ammoniaderivatives of ammonia Classified as primary, secondary, tertiaryClassified as primary, secondary, tertiary

CHCH33 CHCH33

CHCH33——NNHH2 2 CHCH33——NNHH CH CH33——N N — CH— CH33

Primary Primary Secondary Secondary TertiaryTertiary one N-C two N-C three N-Cone N-C two N-C three N-Cbondbond bonds bonds bonds bonds

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Naming AminesNaming Amines

IUPAC aminoalkane IUPAC aminoalkane Common alkylamine Common alkylamineCHCH33CHCH22NNHH2 2

aminoethaneaminoethane (ethylamine)(ethylamine)

NNHH22

||CHCH33CHCHCHCH33

2-aminopropane Aniline2-aminopropane Aniline(isopropylamine)(isopropylamine)

NH2

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22.5 Polymers22.5 PolymersPoly= many; mers=partsPoly= many; mers=parts

Polymers are large, usually Polymers are large, usually chainlike molecules that are built chainlike molecules that are built from small molecules called from small molecules called monomers joined by covalent bondsmonomers joined by covalent bondsMonomerMonomer PolymerPolymerEthyleneEthylene PolyethylenePolyethyleneVinyl chlorideVinyl chloride Polyvinyl Polyvinyl chloridechlorideTetrafluoroethyleneTetrafluoroethyleneTeflonTeflon

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Some common synthetic polymers, their Some common synthetic polymers, their monomers and applicationsmonomers and applications

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Types of PolymerizationTypes of Polymerization

Addition PolymerizationAddition Polymerization:: monomers monomers “add together” to form the polymer, “add together” to form the polymer, with no other products. with no other products. ( Polyethylene and Teflon)( Polyethylene and Teflon)

Condensation PolymerizationCondensation Polymerization:: A A small molecule, such as water, is small molecule, such as water, is formed for each extension of the formed for each extension of the polymer chain. (Nylon)polymer chain. (Nylon)

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Addition PolymerizationAddition Polymerization

OH

C CHH

HH

COH

H CH

H

H

C CHH

HH

COH

H CH

H

H

COH

H CH

H

HC CH H

H H

The polymerization processIs initiated by a free radical

A species with an unpaired electron such as hydroxyl free radical

Free radical attacks and breakThe bond of ethylene moleculeTo form a new free radical

• Repetition of the process thousands of times creates a long chain polymer• The process is terminated when two radicals react to form a bond; thus there will be no free radical is available for further repetitions.

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Condensation PolymerizationCondensation PolymerizationFormation of NylonFormation of Nylon

NH

H(CH2)6 N

H

H CO

O (CH2)4H CO

O HHexamethylendiamine Adipic acid

NH

H(CH2)6 N

HC (CH2)4 C

O

O H

O+ H2O

• Small molecule such as H2O is formed from each extension of the polymer chain• both ends are free to react

Dimer

Diamine Dicarboxylic acid

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NH

(CH2)6 NH

( C (CH2)4 COO

)n

Nylon