Ch21_complete_081511 - Chapter 21: Organic and Biochemical...

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Chapter 21: Organic and Biochemical Molecules 21.1 Alkanes: Saturated Hydrocarbons 21.2 Alkenes and Alkynes 21.3 Aromatic Hydrocarbons 21.4 Hydrocarbon Derivatives 21.5 Polymers 21.6 Natural Polymers
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Organic Chemistry Study of compounds with C–C and/or C–H bonds . Hence excludes NaCN, CO, CS 2 , CCl 4 , etc. Basic Principles 1. C forms 4 covalent bonds: single bonds to C, H, N, O, S, and Cl; double bonds to C, N, O, and S; triple bonds to C and N. – With all bonds single, C is sp 3 (tetrahedral) examples: CH 2 Cl 2 , C 2 H 6 – With a double bond, C is sp 2 (trigonal planar) examples: H 2 C=O, F 2 C=CF 2 – With a triple bond, C is sp (linear) example: CH 3 C N
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2. C–H and C–C single bonds are unreactive. C–(N, O, S, Cl) single bonds are somewhat reactive. Double and triple bonds are the most reactive. Reactivity comes from some combination of polarity and bond weakness: • C–H and C–C bonds are nonpolar and strong. • C–N, C–O, and C–Cl bonds are polar and strong. • C–S bonds are nonpolar and weak. • Double and triple bonds vary in polarity and have a weak part [ bond(s)]. Organic Chemistry
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3. Compounds are classified by their functional groups (example >C=O, carbonyl group). A given functional group reacts similarly in all molecules. – Symbol R means any hydrocarbon (C n H 2n+1 ) chain attached to a functional group. Example: RCH=O represents CH 3 CH=O, C 2 H 5 CH=O, C 3 H 7 CH=O, … Organic Chemistry
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Carbon Skeleton Drawings Carbon skeleton drawings are a quick, simple way to draw organic compounds Hydrogens are not drawn, but implied Carbons are not labeled, but occur at the bend in the line Examples: – ethane – pentane – acetic acid – benzene – cholesterol
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Alkanes Recall the sp 3 hybridized carbon sp 3 carbon is tetrahedral Carbon always makes four bonds Alkanes are chains of carbon-carbon single bonds – all sp 3 ; “saturated” Low number of carbons (1-4) tend to be gases
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Ways of depicting formulas and models of an alkane Carbon skeleton
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Numerical Roots for Carbon Chains and Branches Number of C atoms Roots 1 2 3 4 5 6 8 7 9 10 meth- eth- prop- but- hex- pent- hept- oct- non- dec- Alkane names: Prefix (below) plus “-ane”
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Structural isomers – same atoms, different connectivity C n H 2n+2
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Figure 21.2: Lewis and Molecular Structure of Ethane C 2 H 6 CH 3 CH 3
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Figure 21.3: Structures of Propane and Butane C 3 H 8 CH 3 CH 2 CH 3 C 4 H 10 CH 3 CH 2 CH 2 CH 3
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Figure 21.4: Normal Butane and Isobutane C 4 H 10 CH 3 CH 2 CH 2 CH 3 C 4 H 10 CH 3 CH(CH 3 ) 2 “iso” – branch at end of chain (2 CH 3 groups) Isomers of butane
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Isomers of pentane “iso” – branch at end of chain (2 CH 3 groups) “neo” – 2 branches at end of chain (3 CH 3 groups)
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1 4 2 3
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This note was uploaded on 01/19/2012 for the course CHEM 162 taught by Professor N. during the Summer '08 term at University of Washington.

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Ch21_complete_081511 - Chapter 21: Organic and Biochemical...

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