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ORGANIC CHEMISTRY
Campbell and Reece Chapter 4
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Organic Chemistry
study of carbon compounds (most also have hydrogen)
range from small molecules (methane has 4 atoms) to very large one (proteins can have thousands of atoms)
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Major Elements of Life
Carbon Hydrogen Oxygen Nitrogen Sulfur Phosphorus
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Carbon is very Versatile
because C can form 4 covalent bonds these 6 elements can form an almost limitless # organic molecules
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VITALISM
Some credit Hippocrates Simply stated: there is a
life force outside physical & chemical laws
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Jons Jakob Berzelius
Swedish chemist in early 1800’s
“Organic compounds come from living things” (only )
so inorganic compounds found only in nonliving things
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Fredrich WÖhler German chemist 1828: synthesized urea in
lab (normally made in kidney)
Did not convince Vitalists because he 1 reactant he used came from animal blood
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Urea
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Hermann Kolbe
Student of Wohler Synthesized urea using
only inorganic reactants….. Crushed Vitalism…..sorry
Yoda
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Origin of Life on Earth
Stanley Miller, 1953 Designed experiment
trying to re-create conditions on early Earth
Hypothesized : abiotic synthesis of organic compounds possible
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Miller’s Experiment
Closed system Flask of water (early seas)
heated Water vapor rose to another
higher chamber containing “atmosphere”
Sparks added (lightening) “rain” formed, cooled material
collected analyzed
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Miller’s Experiment
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Miller’s Conclusion
Complex organic compounds could form spontaneously under conditions thought to exist on early Earth
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Miller’s Results
2008: re-analyzed some samples from Miller’s experiments in the 1950’s
Additional organic compounds identified
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Organic Chemistry
Definition changed to: Study of Carbon
Compounds (regardless of origin)
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Bonding with Carbon
C has 4 valence e- Bonds possible:
4 single covalent bonds 2 single & 1 double covalent
bond 2 double covalent bonds 1 single & 1 triple covalent
bond
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Bonding with Carbon
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Carbon Skeletons
Carbon chains form the backbone of most organic molecules
These skeletons can be Straight
Branched
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Carbon Skeleton Variation
In rings:
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Carbon Skeleton Variation
1 important source of molecular complexity & diversity that characterizes living organisms
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Hydrocarbons
C & H Major components of petroleum
products (fossil fuels) When organism dies all water
soluble compounds wash away as it decays.
Fats stay behind hydrocarbons Burn fossil fuels because they
release a large amount of energy
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Fossil Fuels
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Isomers Cpds with same # and types
of atoms but they are arranged differently
Different structures behave differently
3 types:1. Structural Isomers2. Cis/trans Isomers3. enantiomers
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Structural Isomers
Differ in covalent arrangements of their atoms
Molecular formula same, structure different
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Structural Isomers
# possibilities for different arrangements of atoms increases dramatically as carbon skeleton increases in size
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Cis-trans Isomers
aka geometric isomers Carbons have covalent
bonds with same atoms but these atoms differ in their spatial relationship
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Cis-trans Isomers
In cis groups are on same side of Carbon
In trans groups are across from each other
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Cis-trans Isomers The difference in cis-trans
can dramatically affect the biological behavior of the molecule
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Enantiomers
Isomers that are mirror images of each other
Differ in shape due to having asymmetric carbon
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Enantiomers
Usually only 1 is biologically active
Other 1 may have much milder effect
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Functional Groups
Portion of molecule that participates in chemical reactions in a characteristic way
7 common, & very important functional groups in organic chemistry
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HYDROXYL-OH
Make alcohols Properties:1. Polar2. Can for H-Bonds with
water (help cpd dissolve in water)
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CARBONYL-C=O
Makes:1. Ketones: if in middle of
molecule2. Aldehyde: if at end of
molecule Properties:1. can be isomers2. ketoses/aldoses
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CARBOXYL-COOH
Makes: organic acids Properties:1. Can donate H+ COO-2. Mostly found in cells in
ionized form (charge of -1) & called a carboxylate ion
3. In amino acids
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CARBOXYL
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AMINO-NH2
Makes: Amines Properties:1. Acts as a base (can take H+)2. Found in cells in ionized
form with +1 charge3. in amino acids
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AMINE
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SULFHYDRYL-SH
Makes: thiols Properties:1. 2 –SH can react forming
disulfide bridges These bridges make
hair curly
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PHOSPHATE-PO4
Structure: 2 O have (-) charge
Makes: Organic phosphates
Properties: Makes molecule polar (-1)
charge when in middle, (-2) when on end
Can react with water energy
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PHOSPHATE
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METHYL-CH3
Makes: Methylated compounds
Properties: When attached to DNA, affects
expression of genes Attachment to Testosterone
changes biological effect compared to Estrogen (without methyl group)
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METHYL
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ADENOSINE TRIPHOSPHATE
ATP Made of adenosine + 3 phosphate groups
When 3 phosphates in series, easy to remove 3rd group with water
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Hydrolysis of ATP