John C. Kotz • State University of New York, College at Oneonta
John C. KotzPaul M. TreichelJohn Townsend
http://academic.cengage.com/kotz
Chapter 10Carbon: More Than Just Another Element
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Important – Read Before Using Slides in Class
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ORGANIC CHEMISTRYORGANIC CHEMISTRYORGANIC CHEMISTRYORGANIC CHEMISTRY
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cinnamaldehyde
eugenol
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Types of Organic Types of Organic CompoundsCompounds
• Vast majority of over 20 million known compounds are based on C: organic compounds.organic compounds.
• Generally contain C and H + other elements
• Great variety of compounds
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IsomerismIsomerism• Isomers Isomers have identical composition have identical composition but different structuresbut different structures
• Two forms of isomerismTwo forms of isomerism– Constitutional (or structural)Constitutional (or structural)– StereoisomerismStereoisomerism
• ConstitutionalConstitutional– Same empirical formula but different Same empirical formula but different atom-to-atom connectionsatom-to-atom connections
• StereoisomerismStereoisomerism– Same atom-to-atom connections but Same atom-to-atom connections but different arrangement in space.different arrangement in space.
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Structural IsomersStructural Isomers
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Cis-2-buteneCis-2-butene
Stereoisomers: Stereoisomers: GeometricGeometric
Geometric isomers can occur when there is a C=C double bond.
Trans-2-buteneTrans-2-butene
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• Optical isomersOptical isomers are molecules are molecules with non-superimposable mirror with non-superimposable mirror images.images.
• Such molecules are called Such molecules are called CHIRALCHIRAL• Pairs of chiral molecules are Pairs of chiral molecules are enantiomersenantiomers..
• Chiral molecules in solution can Chiral molecules in solution can rotate the plane of plane rotate the plane of plane polarized light.polarized light.
Stereoisomers: Stereoisomers: OpticalOptical
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Chiral Compounds—Polarized Chiral Compounds—Polarized LightLight
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Stereoisomers Stereoisomers IsomersIsomers
Chirality Chirality generally generally occurs when occurs when a C atom has a C atom has 4 different 4 different groups groups attached.attached.Lactic acid
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Stereoisomers Stereoisomers IsomersIsomers
Lactic acid isomers Lactic acid isomers are are nonsuperimposablenonsuperimposable
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Chirality: Chirality: Handedness in NatureHandedness in Nature
These molecules are non-These molecules are non-superimposable mirror superimposable mirror
images.images.
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Chirality: Chirality: Handedness in NatureHandedness in Nature
These amino acids are non-superimposable These amino acids are non-superimposable mirror images.mirror images.
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Stereoisomers in Stereoisomers in NatureNature
Right- and Right- and left-handed left-handed seashellsseashells The DNA here The DNA here
is right-is right-handedhanded
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The egg cases of The egg cases of the whelk have a the whelk have a right-handed right-handed twist.twist.
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• Compounds of C and HCompounds of C and H• Subgroups: Subgroups: –Alkanes: C-C single bondsAlkanes: C-C single bonds–Alkenes: C=C double bondsAlkenes: C=C double bonds–Alkynes: carbon-carbon Alkynes: carbon-carbon triple bondstriple bonds
–Aromatic: based on benzeneAromatic: based on benzene
HydrocarbonsHydrocarbons
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• Alkanes have the general Alkanes have the general formula Cformula CnnHH2n+22n+2
• CHCH44 = methane = methane
• CC22HH66 = ethane = ethane
• CC33HH88 = propane = propane
• CC44HH10 10 = butane= butane
• CC55HH1212 = pentane = pentane
HydrocarbonsHydrocarbons
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Methane Hydrate, CHMethane Hydrate, CH44(H(H22O)O)xx
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Pentane
2-Methylbutane
2,2-Dimethylpropane
CH3CH2CH2CH2CH3
CH3CHCH2CH3
CH3
H3CCCH3
CH3
CH3
Hydrocarbons Hydrocarbons & Structural & Structural IsomerismIsomerism
CC55HH1212 has 3 has 3 structural structural isomers.isomers.
CC66HH1414 has 5 has 5
CC77HH1414 has 9 has 9
CC55HH1212 has 3 has 3 structural structural isomers.isomers.
CC66HH1414 has 5 has 5
CC77HH1414 has 9 has 9
Isomers of CIsomers of C55HH1212??Isomers of CIsomers of C55HH1212??
Note names of isomersNote names of isomersNote names of isomersNote names of isomers
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Alkanes are colorless Alkanes are colorless gases, liquids, and solidsgases, liquids, and solids
Generally unreactive (but Generally unreactive (but undergo combustion)undergo combustion)
Not polar (or low polarity) Not polar (or low polarity) and so are not soluble in and so are not soluble in water.water.
Hydrocarbons: Hydrocarbons: AlkanesAlkanes
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All compounds are flexible. All compounds are flexible.
Cyclohexane, CCyclohexane, C66HH1212, has interconverting , has interconverting “chair” and “boat” forms.“chair” and “boat” forms.
Hydrocarbons: Hydrocarbons: CycloalkanesCycloalkanes
Axial H atom
Equatorial H atom
Chair form Boat form
123
56
1
23
44
5 6
H H
H
H
H
H
H
H
H
H
H
H
HH
H
H
H
H
H
H
H
H
H
H
H
H
H
H
HH
H
H
H
H
H
Chair form
1
6
2
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5
H
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Alkenes: Compounds Alkenes: Compounds with C=C Double Bondswith C=C Double Bonds
• How many isomers are possible for How many isomers are possible for a compound with the formula Ca compound with the formula C44HH88??
CH3
CC
H
CH3H
H
CC
H
CH3H3C
H
CC
H3C
CH3H
2-methylpropene(isobutene)
cis-2-butene trans-2-butene
H
CC
H
CH2CH3H
1-butene
1 2
3 4
1
1
1
2
3
2 23 3
4 4
CH3
CC
H
CH3H
H
CC
H
CH3H3C
H
CC
H3C
CH3H
2-methylpropene(isobutene)
cis-2-butene trans-2-butene
H
CC
H
CH2CH3H
1-butene
1 2
3 4
1
1
1
2
3
2 23 3
4 4
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Alkenes—Alkenes—Many Occur NaturallyMany Occur Naturally
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Reactions of Alkenes:Reactions of Alkenes:ADDITION REACTIONSADDITION REACTIONS
• Alkenes are Alkenes are unsaturated unsaturated — more — more bonds can form to the C atomsbonds can form to the C atoms
• Molecules such as BrMolecules such as Br22, H, H22, HCl, , HCl,
HBr, and HHBr, and H22O O addadd to the double bond to the double bond
C CCH
H
H
HC
Br BrH H
HH
+ Br2
1,2-dibromoethane
C CCH
H
H
HC
Br BrH H
HH
+ Br2
1,2-dibromoethane
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An Addition ReactionAn Addition Reaction
• The fat in bacon is partially The fat in bacon is partially unsaturated. The fat adds Brunsaturated. The fat adds Br22 to to the C=C bonds.the C=C bonds.
• Fats can be “hydrogenated” with HFats can be “hydrogenated” with H22..
Fat Fat placed in placed in BrBr22 vapor vapor
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An Addition ReactionAn Addition Reaction
Fat Fat placed in placed in BrBr22 vapor vapor
PLAY MOVIE
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An Addition ReactionAn Addition Reaction• Fats can be “hydrogenated” with HFats can be “hydrogenated” with H22..
Peanut butter has partially Peanut butter has partially hydrogenated vegetable oil.hydrogenated vegetable oil.
Peanut butter has partially Peanut butter has partially hydrogenated vegetable oil.hydrogenated vegetable oil.
PLAY MOVIE
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Trans Fatty Acids
tend to raise total blood cholesterol
CHCH33(CH(CH22))77CH=CH(CHCH=CH(CH22))77COCO22H H
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Trans Fatty AcidsTrans Fatty AcidsFood Percentages of Trans-Fatty Acids
Butter 3.6
Soft Margarine 5.2
Hard Margarine 12.4
Vegetable Oils, Including Safflower, Sunflower, and Soy
0
Beef burger, Fried or Grilled
0.8
Chocolate Cake with Icing 7.1
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AlkynesAlkynes
• Alkynes have carbon-carbon triple bonds. Alkynes have carbon-carbon triple bonds.
• CC22HH22: common name = acetylene: common name = acetylenesystematic name = ethynesystematic name = ethyne
Preparation:Preparation:
CaCCaC22(s) + H(s) + H22O(liq) --O(liq) --
> >
C C22HH22 (g) + (g) +
Ca(OH)Ca(OH)22(s)(s)∆∆ffHHoo(C(C22HH22, g) = +226.7 , g) = +226.7 kJ/molkJ/mol
Preparation:Preparation:
CaCCaC22(s) + H(s) + H22O(liq) --O(liq) --
> >
C C22HH22 (g) + (g) +
Ca(OH)Ca(OH)22(s)(s)∆∆ffHHoo(C(C22HH22, g) = +226.7 , g) = +226.7 kJ/molkJ/mol
∆∆rrH for CH for C22HH22 + O + O22 = –1300 kJ/mol= –1300 kJ/mol
∆∆rrH for CH for C22HH22 + O + O22 = –1300 kJ/mol= –1300 kJ/mol
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Aromatic CompoundsAromatic Compounds
• Benzene, CBenzene, C66HH66, in , in the top 25 the top 25 chemicals chemicals produced in the produced in the U.S. U.S.
• Starting point Starting point for hundreds of for hundreds of other compounds.other compounds.
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Resonance in BenzeneResonance in Benzene
• CC66HH66 has two resonance structures with has two resonance structures with alternating double bonds. alternating double bonds.
• The π electrons are The π electrons are delocalizeddelocalized over the ring. over the ring.
CC
CC
C
CC
C
CC
C
C
H
H
HH
H H
H
H
HH
H H
CC
CC
C
C
H
H
HH
H H
Resonance structures of benzene, C6H6 Abbreviated representation of resonance structures
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Resonance in BenzeneResonance in Benzene
• CC bond order is _______________CC bond order is _______________• C–C single bond = 154 pm C–C single bond = 154 pm C=C bond = 134 pmC=C bond = 134 pm
• CC bonds in benzene = 139 pmCC bonds in benzene = 139 pm
π electrons delocalizedπ electrons delocalized
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Bonding in BenzeneBonding in Benzene
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Other Aromatic Other Aromatic HydrocarbonsHydrocarbons
TolueneToluene NaphthaleneNaphthalene
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Benzene DerivativesBenzene Derivatives
AnilineAnilineCC66HH55NHNH22
PhenolPhenol
CC66HH55OHOH
TNTTNTtrinitrotoluenetrinitrotoluene
CC66HH44CHCH33(NO(NO22))33
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Naming Benzene Naming Benzene DerivativesDerivatives
1,4-dimethylbenzeneCommon name: Para-xylene
Cl
Ortho to Cl
Meta to Cl
Para to Cl
12
3
4
5
6
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Reactions of AromaticsReactions of Aromatics• SubstitutionsSubstitutions — not additions — are typical.
+ CH3Cl
CH3
+ HClAlCl3
AlClAlCl33 is a catalyst. Catalysts is a catalyst. Catalysts typically used in aromatic typically used in aromatic
substitutions.substitutions.
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Functional GroupsFunctional Groups
See Chemistry Now, Chapter 10See Chemistry Now, Chapter 10See Chemistry Now, Chapter 10See Chemistry Now, Chapter 10
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AlcoholsAlcohols• Characterized by –OH groupCharacterized by –OH group• Name: add –ol to name of Name: add –ol to name of hydrocarbonhydrocarbon
MethanolMethanol
ButanolButanol
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Structures of AlcoholsStructures of Alcohols
CC33HH55OH: how many structural isomers?OH: how many structural isomers?
C C C OH
H
H
H
H
H
H
H
1-propanol
C C C H
H
H
OH
H
H
H
H
2-propanol
Naming:Naming: Add -ol to name of 3-C hydrocarbon. Add -ol to name of 3-C hydrocarbon. Indicate position of OH with number.Indicate position of OH with number.
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Alcohol PropertiesAlcohol Properties• Alcohols are a derivative of water Alcohols are a derivative of water • Many alcohols dissolve in waterMany alcohols dissolve in water
Methanol Methanol dissolves in dissolves in water.water.
Methanol Methanol dissolves in dissolves in water.water.
Butanol is NOT Butanol is NOT soluble in water. soluble in water.
Butanol is NOT Butanol is NOT soluble in water. soluble in water.
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““Sterno”Sterno”
• Alcohols burn in Alcohols burn in
air air
• A mixture of A mixture of
ethanol + calcium ethanol + calcium
acetate = STERNOacetate = STERNO
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GLYCOLSGLYCOLSAlcohols with Two OH Alcohols with Two OH
GroupsGroups
EthyleEthylene ne glycolglycol
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Alcohol ReactionsAlcohol ReactionsScreen 11.6Screen 11.6
SubstitutionSubstitution Elimination—Elimination—the reverse the reverse of of additionaddition
PLAY MOVIEPLAY MOVIE
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TYPES OF ALCOHOLSTYPES OF ALCOHOLS
R C OH
H
H
R C OH
R
H
R C OH
R
R
CH3CH2OH, ethanol
rubbing alcohol H3C C OH
CH3
H
Primary
Secondary
Tertiary
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More Alcohol ReactionsMore Alcohol Reactions
Ethanol is a Ethanol is a PRIMARY PRIMARY ALCOHOLALCOHOL. It is . It is oxidized to an oxidized to an ALDEHYDE and then to ALDEHYDE and then to an ACID.an ACID.
C
C
C
H H
H OH
HH
(l)
C
H O
H OH
H
(l)
Ethanol
+ Oxidizing agent
Acetic acid
+ Oxidizing agentC C
H O
H H
H
(l)
Acetaldehyde
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More Alcohol ReactionsMore Alcohol Reactions
SECONDARY ALCOHOLS SECONDARY ALCOHOLS are oxidized are oxidized to KETONES — and reaction stops to KETONES — and reaction stops there. there.
R—C—R'
oxidizing agent
R—C—R'
O
Secondary alcohol KetoneH
(–R and –R' are organic groups. They may be the same or different.)
OH
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Sugars: Related to Sugars: Related to AlcoholsAlcohols
• Sugars are carbohydrates, compounds Sugars are carbohydrates, compounds with the formula Cwith the formula Cxx(H(H22O)O)yy..
What is the difference between What is the difference between and and D-glucose?D-glucose?
What is the difference between What is the difference between and and D-glucose?D-glucose?
O
H
HO
H
HO
HOHH
OH
OHCHO
OHH
HHO
OHH
OHH
CH2OH
O
H
HO
H
HO
OHOHH
H
OH
1
23
4 5
12
3
45
1
2
3
4
5
-D-glucose β-D-glucose
Open chain form
H H
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Sucrose and RiboseSucrose and Ribose
O
CH2OH
CH2OHH
HOOH
H
H
O
H
HO
H
HO
H
OOHH
H
OH
-D-Glucose
Fructose
O
HOH
HHHH
HOOHO
HOH
HHHH
HOOH
DeoxyriboseDeoxyribose, the sugar , the sugar in the DNA in the DNA backbone.backbone.
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AminesAminesAminesAminesAlcohols are derivatives of HAlcohols are derivatives of H22O O (R–OH) and (R–OH) and aminesamines are are derivatives of NHderivatives of NH33..
MethylamineMethylamine DimethylamineDimethylamine TrimethylamineTrimethylamine
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AminesAminesAminesAminesAmines generally have terrible
odors!
CadaverineCadaverine
PyridinePyridine
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AminesAminesAminesAminesAmines, like NHAmines, like NH33, are bases, are bases
2 C6H5NH2(aq) + H2SO4(aq) 2 C6H5NH3+(aq) + SO4
2-(aq)
Aniline Anilinium ion
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AminesAminesAminesAmines
Many natural Many natural products products and drugs and drugs (such as (such as nicotine nicotine and and cocaine) cocaine) are bases.are bases.
NicotineNicotineHH++
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Compounds with Compounds with Carbonyl GroupCarbonyl Group
AldehydeAldehydeAldehydeAldehyde Carboxylic acidCarboxylic acidCarboxylic acidCarboxylic acid KetoneKetoneKetoneKetone
C
O
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Structures of Structures of AldehydesAldehydes
CinnamaldehydeCinnamaldehyde Odors from aldehydes Odors from aldehydes and ketonesand ketones
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Carboxylic AcidsCarboxylic AcidsBenzoic Benzoic acidacid
Carboxylic acid Carboxylic acid group with group with acidic Hacidic H++
All are All are WEAKWEAK acids acids
Acetic acidAcetic acid
Acids are Acids are found in many found in many natural natural substances: substances: bread, fruits, bread, fruits, milk, winemilk, wine
Acids are Acids are found in many found in many natural natural substances: substances: bread, fruits, bread, fruits, milk, winemilk, wine
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Carboxylic Carboxylic AcidsAcids
C
OC
O O
H
O
CH3
Aspirin, acetylsalicylic acidAspirin, acetylsalicylic acid
Formic acid, Formic acid, HCOHCO22H, gives H, gives the sting to the sting to
ants.ants.
Formic acid, Formic acid, HCOHCO22H, gives H, gives the sting to the sting to
ants.ants.
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Acids + Alcohols --> Acids + Alcohols --> ESTERSESTERS
Esters have generally pleasant odorsEsters have generally pleasant odors
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Acids + Alcohols --> Acids + Alcohols --> ESTERSESTERS
One of the important reactions in nature!One of the important reactions in nature!
H+
O O
CH3COH + CH3CH2OH CH 3COCH2CH3 + H 2O
Acetic acid Ethanol Ethyl acetate
O
RC—O—HH+
O
+ R'—O—H RC—O—R' + H2O
Carboxylic acid Alcohol Ester
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Acids + Alcohols --> Acids + Alcohols --> ESTERSESTERS
Acetic acid
OC CH2CH2CHCH3
O
H3C
CH3
3-methylbutanol
3-methylbutylacetate
Many fruits such as Many fruits such as bananas and bananas and strawberries strawberries contain esters.contain esters.
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GlycerolGlycerolAlcohol with 3 OH GroupsAlcohol with 3 OH Groups
Combine this with long chain acids Combine this with long chain acids ff ??? ???Fatty acids Fatty acids ff fats and oils fats and oils
Combine this with long chain acids Combine this with long chain acids ff ??? ???Fatty acids Fatty acids ff fats and oils fats and oils
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Fats and OilsFats and Oils
R = organic R = organic group with group with NONO C=C bondsC=C bondsCC1212 = Lauric = Lauric acidacidCC1616 = Palmitic = Palmitic acidacidCC1818 = Stearic = Stearic acid acid
R = organic R = organic group with group with NONO C=C bondsC=C bondsCC1212 = Lauric = Lauric acidacidCC1616 = Palmitic = Palmitic acidacidCC1818 = Stearic = Stearic acid acid
O
O
O
H2C
HC
H2C
CRO
CRO
CR
O
R = organic R = organic group group WITHWITH C=C C=C
bondsbondsCC1818 = oleic = oleic
acidacid
R = organic R = organic group group WITHWITH C=C C=C
bondsbondsCC1818 = oleic = oleic
acidacid
What is the What is the functional functional
groupgroup in a fat in a fat or oil?or oil?
What is the What is the functional functional
groupgroup in a fat in a fat or oil?or oil?
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Fats and OilsFats and OilsO
O
O
H2C
HC
H2C
CRO
CRO
CR
O
Fats with C=C bonds are Fats with C=C bonds are usually LIQUDSusually LIQUDS
Fats with C=C bonds are Fats with C=C bonds are usually LIQUDSusually LIQUDS
Oleic acid: a Oleic acid: a monounsaturatmonounsaturated fatty acid ed fatty acid
Oleic acid: a Oleic acid: a monounsaturatmonounsaturated fatty acid ed fatty acid
C=C bondC=C bondC=C bondC=C bond
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Fats and OilsFats and Oils
Fats with saturated acids (no Fats with saturated acids (no C=C bonds) are SOLIDS.C=C bonds) are SOLIDS.
Fats with saturated acids (no Fats with saturated acids (no C=C bonds) are SOLIDS.C=C bonds) are SOLIDS.
O
O
O
H2C
HC
H2C
CRO
CRO
CR
O
Saturated fats Saturated fats are more common are more common in animals. in animals.
Saturated fats Saturated fats are more common are more common in animals. in animals.
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Fats and Polar BearsFats and Polar Bears•Bears gorge on Bears gorge on blubber in the blubber in the winter.winter.
•During the summer During the summer bears rely on bears rely on stored fat for stored fat for energy.energy.
•Burn 1-1.5 kg of Burn 1-1.5 kg of fat per day.fat per day.
•Water for Water for metabolism comes metabolism comes from fat burning.from fat burning.
•Bears gorge on Bears gorge on blubber in the blubber in the winter.winter.
•During the summer During the summer bears rely on bears rely on stored fat for stored fat for energy.energy.
•Burn 1-1.5 kg of Burn 1-1.5 kg of fat per day.fat per day.
•Water for Water for metabolism comes metabolism comes from fat burning.from fat burning.
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Trans Fatty AcidsTrans Fatty Acids•Oleic acid is a mono–Oleic acid is a mono–unsaturated unsaturated cis-cis-fatty acidfatty acid
•Trans fatty acids have Trans fatty acids have deleterious health effects. deleterious health effects.
•Trans fatty acids raise Trans fatty acids raise plasma LDL cholesterol and plasma LDL cholesterol and lower HDL levels.lower HDL levels.
C=C bondC=C bondC=C bondC=C bond
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Fats and Oils: Fats and Oils: SaponificationSaponification
OCH2
CH
CH2
O—HO—H
O—H
Glycerol
+ 3 RC—O- Na +
Sodium stearate, a soap
OO CR
OO CR
CH2
CH
CH2
OO CR
Glyceryl stearate, a fat + NaOH
R = —(CH2)16CH3
+ 3 NaOH
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Acids + Amines --> Acids + Amines --> AMIDESAMIDES
N-methylacetamideN-methylacetamide
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Acids + Amines --> Acids + Amines --> AMIDESAMIDESC
C
C
C
C
C
H
H
N
H
O
HCC
O
H
HH
H
H
Amide link
AcetaminophenAcetaminophenTylenol, Datril, Momentum, ...Tylenol, Datril, Momentum, ...AcetaminophenAcetaminophenTylenol, Datril, Momentum, ...Tylenol, Datril, Momentum, ...
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Alpha-Amino AcidsAlpha-Amino Acids
H
CH3C CO2
NH3
Chiral -carbon
Alanine
C
H
H2N C
O
OH
RAcidAmine
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Peptides and ProteinsPeptides and Proteins
H3NO–
O
HHOCH2H3NO–
O
CH3H
NO–
O
CH3H
H
H3N
O
HHOCH2
peptide bondSerineAlanine
+
Adding more peptide links ---> PROTEINAdding more peptide links ---> PROTEIN
– H2O
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PolymersPolymersPolymersPolymers
• Giant molecules made by Giant molecules made by joining many small molecules joining many small molecules called called monomersmonomers
• Average production is 150 kg Average production is 150 kg per person annually in the per person annually in the U.S.U.S.
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Polymer Polymer ClassificationsClassifications
• ThermoplasticsThermoplastics (polyethylene) (polyethylene) soften and flow when heatedsoften and flow when heated
• ThermosettingThermosetting plastics — soft plastics — soft initially but set to solid initially but set to solid when heated. Cannot be when heated. Cannot be resoftened.resoftened.
• Other classification: Other classification: plastics, fibers, elastomers, plastics, fibers, elastomers, coatings, adhesivescoatings, adhesives
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Polymer PreparationPolymer Preparation
• AdditionAddition polymers — polymers — directly adding monomer directly adding monomer units togetherunits together
• CondensationCondensation polymers — polymers — combining monomer units combining monomer units and splitting out a small and splitting out a small water (water)water (water)
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Polyethylene: Addition Polyethylene: Addition PolymerPolymer
H2C CH2 C C
H
H
H
H
n
n
EthyleneEthylene PolyethylenePolyethylene
A polymer with a molar A polymer with a molar mass of 1emass of 1e66 has about has about 360,000 units.360,000 units.
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Mechanism of Addition Mechanism of Addition PolymerizationPolymerization
PLAY MOVIE
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Types of PolyethyleneTypes of Polyethylene
Linear, high density Linear, high density PE (HDPE)PE (HDPE)
Branched, low Branched, low density PE, LDPEdensity PE, LDPE
Cross-linked PE, Cross-linked PE, CLPECLPE
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Types of PolyethyleneTypes of Polyethylene
CH2CH
OH
CH2CH
OCCH3
CH2CH
n n n
polyvinyl alcohol polyvinyl acetate polystyrene
Polymers based on Substituted Ethylenes, CH2=CHX
O
Table 10.12: others are PVC, Table 10.12: others are PVC, acrylonitrile, polypropylene, polymethyl acrylonitrile, polypropylene, polymethyl
methacrylatemethacrylate
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PolystyrenePolystyrene
• Polystyrene is nonpolar material and Polystyrene is nonpolar material and dissolves in organic solvents.dissolves in organic solvents.
• PS foam is mostly air, and when it PS foam is mostly air, and when it dissolves it collapses to a much smaller dissolves it collapses to a much smaller volume.volume.
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Slime!Slime!
Slime is Slime is polyvinylalpolyvinylalcohol cohol cross-cross-linked with linked with boric acidboric acid
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Bubble Bubble Gum!Gum!A A
copolymercopolymer
Bubble Bubble Gum!Gum!A A
copolymercopolymer
Styrene + butadieneStyrene + butadiene
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Condensation PolymersCondensation Polymers
HOC
O
COH
O
CO
COCH2CH2OO
+ n HOCH2CH2OH
terephthalic acid ethylene glycol
+ H2O
Polyethylene terephthalate (PET), a polyester
n
n
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Polyesters, PETPolyesters, PET
Jackets made from Jackets made from recycled PET soda recycled PET soda bottlesbottles
Soda bottles, Soda bottles, mylar film.mylar film.
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Polyesters: MechanismPolyesters: Mechanism
PLAY MOVIE
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Polyamides: NylonPolyamides: Nylon
PLAY MOVIE
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Polyamides: NylonPolyamides: Nylon
•Each monomer has 6 C atoms in its chain.Each monomer has 6 C atoms in its chain.•A polyamide link forms on elimination of HClA polyamide link forms on elimination of HCl•Result = nylon 66Result = nylon 66•Proteins are Proteins are polyamidespolyamides
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Polymer Recycling Polymer Recycling SymbolsSymbols
LDPE = LDPE = Low density PE = 0.910-0.925 g/cmLow density PE = 0.910-0.925 g/cm33
HDPE = HDPE = High density PE = 0.941-0.965High density PE = 0.941-0.965PP = PP = Polypropylene = 0.90Polypropylene = 0.90V = V = PVC (Vinyl chloride) = 1.30-1.58PVC (Vinyl chloride) = 1.30-1.58