Beruflich Dokumente
Kultur Dokumente
Ch. 1
Hydrocarbons!
Molecular Name Molecular Name
Formula Formula
CH4 methane C6H14 hexane
C2H6 ethane C7H16 heptane
C3H8 propane C8H18 octane
C4H10 butane C9H20 nonane
C5H12 pentane C10H22 decane
Properties of Alkanes:
# of Physical
Carbons State
1-4 gas
5-17 liquid
18 solid
Halogenated Hydrocarbons
o CF3CCl2H (Halothane)
1,1,1-trifluoro-2-bromo-2chloro ethane
1
non-flammable
toxic
Cycloalkanes
Cyclopropane 49
Cyclobutane
90
Cyclopentane
108
Cyclohexane
109
Alkenes:
Formula: CnH2n
Has at least one carbon-carbon double bond
Naming
o Choose the longest carbon chain which contains the double
bond
o Number from the end closest to the double bond
Cis-Trans Isomerism
o Physical properties (BP, density, etc.) of cis and trans
isomers differ
Physical properties similar to alkanes
o Density < 1g/mole
o Insoluble in H2O
Chemical properties
o Addition
Hydrogen
Halogens
Hydrogen Halide
o HBr, HCl, etc.
2
o Combustion
Alkynes
Formula: CnH2n-2
Has at least one carbon-carbon triple bond
Naming
o Choose the longest carbon chain which contains the triple
bond
o Number from the end closest to the triple bond
Physical properties similar to alkanes and alkenes
Chemical properties similar to alkenes
Aromatics
Benzene
3
Benzene is also pictured as because it has a resonance
structure.
Aromatic Compounds
Toluene (methylbenzene)
Chlorobenzene
1,4-dichlorobenzene (para-dichlorobenzene)
1-chloro-2-methylbenzene
(ortho-chlorotoluene or 2-chlorotoluene)
4
Physical properties similar to other hydrocarbons
o Liquid (6 carbon atoms)
Chemical properties
o Substitution
Halogens
Nitric Acid
Nitrobenzen
e
2,4,6-trinitrotoluene (TNT)
2,4,6-trinitro-methylbenzene?
Petroleum
Straight chain n-alkanes
Some branched near the ends
13-15 Carbons
Octane Number of a gasoline: %
isooctane in an isooctane-heptane
mixture that gives the same 15-17 Carbons
performance of the gasoline
5
2,2-dimethylbutane (CH3)3CCH2CH3 94
2,2,4- 100
trimethylpentane
isooctane
benzene 101
toluene 112
Catalytic Converter
Finely divided metal (Pd or Pt)
Pd
2CO + O2 2CO2
Pd
CnH2n+2 CO2 + H2O
Unburned
6
CH3CHCH3 2-propanol isopropanol
OH isopropyl alcohol
(rubbing)
HOCH2CH2OH 1,2-ethanediol ethylene glycol
1,2-dihydroxy ethane
HOCH2CHCH2OH 1,2,3-propanetriol glycerol
OH 1,2,3- glycerine
trihydroxypropane
hydroxybenzene phenol
Alcohol Oxidization
Oxidization agent
o KMnO4
o K2Cr2O7
Primary alcohols oxidize to aldehydes
Secondary alcohols oxidize to ketones
Tertiary alcohols do not oxidize
Phenols
Phenols are easily oxidized to give a mixture of products
Phenol is a weak acid
o Ka 10-10
Ethers
Formed when two alcohols react
o ROH + HOR R O R + H2O
7
Physical Properties
o Boiling Point
o Solubility
5 Carbons are water soluble
Chemical Properties
o Ethers oxidize to form peroxides
methoxybenzene
2-butyl-4- butylated
methoxybenzene hydroxyanisole
Physical Properties
o BP
o Solubility
Chemical Properties
o Oxidation (aldehydes only) to a carboxylic acid
o Aldehydes reduce to a primary alcohol
o Ketones reduce to a secondary alcohol
o Aldehydes react with alcohols to form the unstable
hemiacetal
8
The hemiketal then becomes a ketal
ethanal acetaldehyde
propanal propionaldehyde
2-hydroxybutanal -
hydroxybutyraldehyd
e
benzaldehyde
4-hydroxy-3- vanillin
methoxybenzaldehyde
propanone acetone
2-butanone methylethylketone
(MEK)
acetophenone
benzophenone
9
butyrophenone
Carboxylic Acids
General Formula:
Physical Properties
o Solubility
<5 Carbons are water soluble
o Boiling Point
Unusually high due to hydrogen bonding
Chemical Properties
o Weak Acids
Neutralize to form a salt and water
Naming salts
Name the cation, and then write the name of
the anion with the ending oate
benzoic acid
4-aminobenzoic acid
10
octadecanoic acid stearic acid
Esters
General Formula:
ethyl heptanoate
11
Amines
General Formula:
Physical Properties
o Boiling Point
Primary and secondary have high BPs but not tertiary
o Solubility
<5 carbons are water soluble
Chemical Properties
o Ionization
NH3 + H2O NH4+ + OH-
RNH2 + H2O RNH3+ + OH-
R2NH + H2O R2NH2+ + OH-
R3N + H2O R3NH+ + OH-
o Neutralization
NH3 + HCl RNH2 HCl
RNH3 + HCl RNH2 HCl
R2NH + HCl RNH2 HCl
Molecular Formula IUPAC Common Name
methyl amine
dimethyl amine
1,6-hexanediamine 1,6-diaminohexane
aminobenzine aniline
1-amino-2-
phenylethene
1-phenyl-2- amphetamine
aminopropene
12
methamphetamine
1-phenyl-2- P2P
hydroxypropane
Amides
General Formula:
o Neutral
ethanamide acetamide
Thiols (Mercaptans)
General Formula: R-S-H
13
Nitriles (Cyanides)
General Formula:
Addition Polymers
Made by adding monomer units (usually containing C=C)
directly together
Pressure (1000-3000
o n CH2=CH2 Heat (100-250C)
atm)
Polyethylene
o Polypropylene
o Polystyrene
polyphenylethene
Not reactive
o Polyhalogenated Alkenes
Vinyl Chloride
Poly-tetrafluoroethene (Teflon)
Poly-1,1-dichloroethene (Saran)
14
Polyethylene terephthalate (Dacron)
Polypropylene
Polystyrene
Hot Dog
15
Acrylics
o Acrylic acid Polyacrylic acid
o Polyisoprene
Isoprene
Poly-trans-isoprene (brittle)
Vulcanization
Vulcanized natural rubber is used for tires
16
Condensation Polymers
Monomer units (usually containing different functional groups)
combine to lose a small molecule (HCl, H2O)
Polyesters
o Alcohol + carboxylic acid ester + H2O
o Diol + dicarboxylic acid polyester + H2O
Ethylene glycol + terephthalic acid
polyethylene
terephthalate
Polyamide
o Primary amine + Carboxylic acid amide + H2O
o Diamine + diacid polyamide (nylon) + H2O
o Nylon A, B
A is the number of carbons in the diamine
B is the number of carbons in the diacid
Polymers in general
Molecular weight
o M = n mo
17
n is the degree of polymerization
mo is the molar mass of the repeated unit
o Weight must be at least 10,000 before the polymer
becomes useful
n M Physical State
1 1(28) = 28 gas
2 2(28) = liquid
4 4(28) = liquid
100 100(28) = 2800 solid
200 200(28) = 5600 solid
10,000 resin (plastic) / useful
polymer
Temperature Transitions
o Glass transition temperature, Tg , comes before the melting
point, Tm
o polymer (s) polymer (s) polymer (l)
Brittle Tg flexible Tm
liquified
Isomerism
Structural isomers
o Same molecular formula, but different connectivity
1-propanol 2-propanol
methoxyethane
Geometric isomers
o Same molecular formula, same connectivity, but different
arrangements in space
18
o Cis-trans isomerism
Optical Isomerism
o Achiral can superimpose mirror images
o Chiral cannot superimpose mirror images
Asymmetric C carbon bonded to 4 different atoms
or groups of atoms
o Fischer projections
Chiral carbon goes in the middle
When the heavier group is on the left, its the L-
enantiomer
When the heavier group is on the right, its the D-
enantiomer
Glyceraldehyde
L-glyceraldehyde D-glyceraldehyde
(-) (+)
Carbohydrates
Monosaccharides
o Cn(H2O)n
o Aldoses hydroxy aldehydes
v
H H H H
C=O C=O C=O C=O
19
CHOH CHOH CHOH CHOH
CH2OH CHOH CHOH CHOH
CH2OH CHOH CHOH
CH2OH CHOH
CH2OH
o Aldotetroses
o Aldopentoses
D- D- D- D- L- L- L- L-
ribose
Cyclic Sugars
o D-aldohexose (straight chain) cyclic hemiacetal
20
-D-aldohexose -D-aldohexose
-D-glucose -D-glucose
#1 is the anomeric carbon
o Reactions
Oxidation
Aldoses and Ketoses oxidize to carboxylic acids
Any sugar (except sucrose) can be oxidized
Formation of Ethers
2 sugars disaccharide
21
Contains no C-C double bonds
Saturated fatty
acid
Contains C-C double bonds Unsaturated fatty
acid
Oleic acid
3 types of soaps
o anionic
o cationic
o nonionic (in green cleaners)
o Soaps/Detergents
Carboxylates
Bar soap
22
Ex. Sodium Stearate
Not always soluble in water
Sulfonates
Shampoo soap
Ex. Sodium Sulfonate
Soluble in water
o Steroids
Testosterone
One ketone group
Anabolic
Androstenedione
Two ketone groups
Nonanabolic
1-methyl-3-oxoandrost-1-en-17-ylacetate
Ester group
Anabolic
Testing for testosterone
The normal ratio for testosterone (T) to
epitestosterone (E) is about 1T:1E. A ratio of
>6T:1E is illegal in sporting competitions.
Proteins
Polyamide polymers built from amino acids
23
Amino Acid
Pentapeptides
o Five amino acids joined by peptide bonds
o Structure and activity are related
Certain structural features occupy certain receptor
sites
Morphene Codeine
similar structural features - both are used as painkillers
24
Polypeptides
o ex. Insulin (51 amino acids)
o ex. Human Growth Hormone (HGH) (191 amino acids)
o Structure - Proteins
1. Primary
Sequence of amino acids
2. Secondary
H-bonding between peptides
helix (most common)
pleated sheet
3. Tertiary
Interaction between side (R) groups
4. Quaternary
Aggregation > 1 protein molecule
ex. 4 hemoglobin molecules
o Hydrolysis of peptides
1. HCl
HCl
-ala-gly-asn-glu-ala- 2 ala + gly + glu +
asp
Most amino acids remain intact with HCl
HCl attacks amide linkage:
o Gln Glu
o Asn Asp
2. Enzyme
Selecive
enzyme
-ala-gly-asn-glu-ala- ala-gly + asn-glu-
ala
Nucleic Acids
Genetic material
-D-ribose -D-2-deoxyribose
(RNA) (DNA)
25
Adenine Cytosine Guanine Thymine Uracil
(DNA only) (RNA only)
Phosphate linkage
Base pairs
o Adenine pairs with Thymine
DNA RNA
Sugar: -D-2-deoxyribose -D-ribose
N Bases: AGCT AGCU
26
Backbone: Phosphate linkage
Secondary Structure: Double-helix Usually single-
stranded
Replication
27
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