General Chemistry I 1 BONDING IN ORGANIC MOLECULES 7.1 Petroleum Refining and the Hydrocarbons 7.2 The Alkanes 7.3 The Alkenes and Alkynes 7.4 Aromatic Hydrocarbons 7.5 Fullerenes 7.6 Functional Groups and Organic Reactions 7.7 Pesticides and Pharmaceuticals 7 CHAPTER General Chemistry I
7. BONDING IN ORGANIC MOLECULES. CHAPTER. 7.1 Petroleum Refining and the Hydrocarbons 7.2 The Alkanes 7.3 The Alkenes and Alkynes 7.4 Aromatic Hydrocarbons 7.5 Fullerenes 7.6 Functional Groups and Organic Reactions 7.7 Pesticides and Pharmaceuticals. - PowerPoint PPT Presentation
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General Chemistry I 1
BONDING INORGANIC MOLECULES
7.1 Petroleum Refining and the Hydrocarbons
7.2 The Alkanes
7.3 The Alkenes and Alkynes
7.4 Aromatic Hydrocarbons
7.5 Fullerenes
7.6 Functional Groups and Organic Reactions
7.7 Pesticides and Pharmaceuticals
7CHAPTER
General Chemistry I
General Chemistry I 2
307
Organic Chemistry:the study of the compoundsof carbon
7.1 PETROLEUM REFINING AND
THE HYDROCARBONS
Hydrocarbons:compounds of carbon andhydrogen
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7.2 THE ALKANES309
Normal alkanes, n-alkanes
~ straight-chain (linear) alkanes, CnH2n+2
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Fig. 7.1. Bonding in alkanes involves sp3 hybridized orbitals.
Fig. 7.2. Rotation about C–C bond variable conformations
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‘staggered’ conformer ‘eclipsed’ conformer
(sp3-sp3)(sp3-s)(sp3-s)
Conformers (conformations) are isomers that can be interconverted via bond rotations. They are stereoisomers.
- angle strain energy reducing the stability of small rings (< C5) CCC bond angle smaller than the sp3 tetrahedral angle of 109.5o
angle strainedunstrained
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Fig. 7.7. Conformations of cyclohexane. (a) Chair. (b) Boat.
Cyclohexane, C6H12
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C
CC
C
CC
H2C
H2CCH2
CH2
CH2
H2C
or or
H HH
H
H H
HH
HHH
H
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Branched-Chain Alkanes and Isomerism
Fig. 7.8. Two isomeric hydrocarbons with the molecular formula C4H10.(a) Butane. (b) 2-Methylpropane (branched chain isomer).
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-Branched chain hydrocarbons contain only C-C and C-H single bonds, but not in a straight chain. They are constitutional(structural) isomers of normal alkanes. Isomers are different structures with the same molecular formula.
Constitutional isomers have different atomic connectivities: they can be interconverted only by bond-breaking and bond-making processes.
Morphine ~ natural product from “opium poppy” Codeine ~ also cough suppressant and analgesic Heroin ~ 3,6-diacetylmorphine
2~3 times powerful than morphine and more addictive
Morphine Codeine Heroin
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General Chemistry I 46
A Little Joke on Nomenclature
A research chemist walked into a pharmacy and asks, “Do you have (5,6)-7,8-didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol?”The pharmacist scratched her head and said, “Do you mean codeine?”“That’s it!”, said the chemist, “I can never remember that word!”
General Chemistry I 47
Antibacterial Agents (Antibiotics) Sulfanilamide
Bacteria mistake sulfanilamide for p-aminobenzoic acid
→ Interferes with bacteria’s synthesis of folic acid, Penicillin ~ natural product formed by certain molds
~ Total synthesis by John C. Sheehan (1957)
~ Fermentation (more economic)
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“Steroid nucleus” 3 six-atom rings and 1 five-atom ring
Cholesterol ~ synthesized in the liver from acetate units
via the ‘mevalonate pathway’. It is the biological precursor
to most other steroids
Cortisone ~ secreted from adrenal glands
~ controls metabolism of sugars, fats, and proteins