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06/23/17
Chapter 9, Organic Chemistry, Hill
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http://faculty.uscupstate.edu/rsobczak
Carbon
catenation
tetravalent
isomers
alkanes
hydrocarbons
structural formula
condensed
ball-and-stick
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Chapter 9, Organic Chemistry, Hill
spacefilling
saturated
unfunctionalized
Homologous Series
Homologs
Linear or straight chain
Branched
-ane
Structural isomers
Functional
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Chapter 9, Organic Chemistry, Hill
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positional
Stereoisomers
Geometric – cis & trans
Enantiomers
Chiral carbon
Isomers
Structural
Positional
Stereoisomers
Functional
Enantiomers
Diastereomers
Geometric
Nonpolar
Intramolecular
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Intermolecular
Emollients
Fuels
Paraffin
laxatives & medical lubricants
Cyclo
Cyclopropane
Unsaturated
Alkenes
Alkynes
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Chapter 9, Organic Chemistry, Hill
degree of unsaturation
Lewis dot structure
Intra & intermolecular
Ethylene
Polyunsaturated
Stereoisomers
Geometric
cis, trans
Enantiomers
Acetylene
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Chapter 9, Organic Chemistry, Hill
Propyne
Aromatic
Benzene
Toluene
benzene
H3C
toluene
Cinnamaldehyde
Methyl salicylate
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Chapter 9, Organic Chemistry, Hill
CH
CH
O
CH
cinnamaldehyde
CH3O
O
OH
Methyl salicylate
TNT
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Chapter 9, Organic Chemistry, Hill
CH3
O2N
NO2
NO2
2,4,6-trinitrotoluene
Naphthalene
Anthracene
Phenanthrene
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naphthalene
anthracene
phenanthrene
Heterocyclic
Pyrimidine
Purine
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Chapter 9, Organic Chemistry, Hill
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N
N
pyrimidine
NH
N
N
N
purine
BHA, BHT
Vanillin
Intra & intermolecular
Halogenated Hydrocarbons R-X
CH3Cl, CH2Cl2, CHCl3, CCl4
DDT, TCDD & 2,4-D
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Chapter 9, Organic Chemistry, Hill
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PCBs polychlorobiphenyl
biphenyl
Vinyl chloride, PVC
H2C
CH Cl
vinyl chloride
Intra & intermolecular
Chlorofluorocarbons CFCs
Freons
CFC-11 CCl3F
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Chapter 9, Organic Chemistry, Hill
CFC-12 CCl2F2
CFC-22 CHClF2
Perfluorocarbons
Teflon
Functional Group
Alkyl group
Alcohol R-OH
–anol
Methanol
H3C
OH
methanol
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50%  HCHO
Ethanol
OH
H3C
CH2
ethanol
distillation
Proof
16 H+ + 2Cr2O7-2(yellow-orange) + 3EtOH  3CH3COOH + 4Cr3+(green) +11H2O
Denatured
Fetal alcohol syndrome
isopropyl alcohol
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Chapter 9, Organic Chemistry, Hill
H3C
CH3
CH
OH
isopropyl alcohol
Ethylene glycol
OH
CH2
HO
CH2
ethylene glycol
Propylene glycol
Glycerol – humectant
OH
HO
CH
CH2
OH
CH2
glycerol
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Chapter 9, Organic Chemistry, Hill
Menthol
OH
menthol
Cholesterol
Vitamin A, D2
Phenols ArOH
HO
phenol
Hexylresorcinol
Hydroquinone
o-cresol
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BHA, BHT
Ethers R-O-R’
Diethyl ether
CH3 CH2 O CH2 CH3
diethyl ether
Peroxides
methyl propyl ether
methoxyflurane –
Penthrane CHCl2F2OCH3
MTBE methyl t-butyl ether
CH3
CH3 O C CH3
CH3
methyl t-butyl ether
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Ethylene oxide
O
ethylene oxide
Aldehydes R-CHO, -anal
Ketones R-C(=O)-R, -anone
Formaldehyde/methanal
O
H2 C
formaldehyde
Acetaldehyde/ethanal
O
CH3 CH
acetaldehyde
Benzaldehyde
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CH CH
O
CH C
CH
CH CH
benzaldehyde
Vanillin
CHO
C
HC
CH
HC
C
C
O
CH3
OH
Acetone, propanone
O
CH3 C CH3
Progesterone – Steroid
Organic Acids –anoic acid
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Chapter 9, Organic Chemistry, Hill
RCOOH or RCO2H
Formic or methanoic acid
O
HC
OH
Acetic or ethanoic acid
O
CH3 C OH
acetic acid
propionic acid
O
CH3 CH2 C OH
propionic acid
butyric acid
O
CH3 CH2 CH2 C OH
butyric acid
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Chapter 9, Organic Chemistry, Hill
octanoic acid
O
CH3 (CH2 )6 C OH
octanoic acid
decanoic acid
O
CH3 (CH2 )8 C OH
decanoic acid
benzoic acid
CH CH
O
HO
C
C
CH
CH CH
benzoic acid
lactic acid
OH O
CH3 CH C OH
fatty acid
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Chapter 9, Organic Chemistry, Hill
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stearic CH3(CH2)16CO2H
palmitic (16)
oleic (18/1)
linolenic (18/3)
citric acid
OH
O
HO
C O
O
C CH2 C CH2 C OH
OH
citric acid
oxalic acid
O O
HO
C C OH
oxalic acid
acrylic acid
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Chapter 9, Organic Chemistry, Hill
O
H2 C
CH C OH
acrylic acid
Esters RCOOR’ –ate
Ethyl acetate
O
CH3 C O CH2 CH3
Condensation
Esterification
Isoamylacetate
O
CH3 C O CH2 CH2 CH CH3
isoamyl acetate
CH3
Ethyl hexanoate
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O
CH3 CH2 CH2 CH2 CH2 C O CH2 CH3
ethyl hexanoate
Salicylates
Antipyretic
Analgesic
Anti-inflammatory
acetylsalicylic acid
OH
C
CH
HC
C
HC
C
CH
O
O
O
C
CH3
Methyl salicylate
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OCH3
C
CH
HC
C
HC
C
O
O
CH
H
Triglycerides
O
H2C
O
CH3 (CH2)14 C O
CH
H2C
O C
(CH2)7 CH CH
(CH2)7 CH3
O
O C
(CH2)16 CH3
cis
Amines
Primary, secondary, tertiary
H2 N
CH3
methylamine
CH3 NH CH3
dimethylamine
CH3
CH3 N CH3
Trimethylamine
Aniline
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Chapter 9, Organic Chemistry, Hill
CH CH
H2 N
C
CH
CH CH
aniline
Putrescine
H2N
CH2 CH2 CH2 CH2 NH2
Cadaverine
H2N
CH2 CH2 CH2 CH2 CH2 NH2
Alkaloids
Nicotine
N
HC
CH
HC
C
CH
CH
CH2
N
H3 C
nicotine
CH2
CH2
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Chapter 9, Organic Chemistry, Hill
Caffeine
O
CH3
C
H3 C
N
C
C
C
N
CH
O
N
N
CH3
caffeine
Cocaine
Purines & pyrimidines
Amphetamine
Mescaline
Adrenaline
Vitamins
P-aminoazobenzene
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PABA
Amino acids
H2N-CH2-COOH
Amides RC(=O)NH2
Primary, secondary, tertiary
O
CH3 C NH2
acetamide
O
CH3 C NH CH3
N-methylacetamide
O CH3
CH3 C N CH3
N,N-dimethylacetamide
Nylon, silk, wool, proteins
LSD
Heterocyclic Compounds
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Problems 9.1, 9.2, 9.3, 9.4, 9.5,
9.6, 8, 12, 16, 18, 20, 22, 24, 26,
28, 30, 32, 36, 38, 40, 44, 46, 50,
54, 56, 58, 60, 62, 64, 66, 73, 74