CH04 Instructor Notes

CH04 Instructor Notes - Chapter 4 Alcohols and Alkyl...

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Ch221 Gorman Lecture Notes, Chapter 4 p. 1 of 12 Chapter 4 Alcohols and Alkyl Halides 0. What’s a functional Group? Show some alcohols and alkyl halides I. CHEMICAL REACTIONS YIELDING ALCOHOLS AND ALKYL HALIDES R OH + H X R X + H Alcohol hydrogen halide alkyl halide R H + X 2 R X + H X Alkane Halogen hydrogen h Substitutions one functional group replaces another Mechanism how a chemical reaction occurs (atom and electron motion) II. IUPAC NOMENCLATURE OF ALKYL HALIDES A. Radicofunctional Nomenclature The molecule is named as a halide B. Substitutive Nomenclature The molecules is named with a halide as a substituent F Cl Br Radicofunctional: 1-ethyl-2-methylbutyl fluoride 4,4-dimethyl cyclohexyl chloride 1-ethylpropyl bromide Substitutive: 3-fluoro-4-methyl hexane 1-chloro-4,4-dimethyl cyclohexane 3-bromo pentane IIa. IUPAC NOMENCLATURE OF ALCOHOLS A. Radicofunctional Nomenclature the molecule is named as an alcohol B. Substitutive Nomenclature 1. Name longest chain that bears -OH. 2. Remove -e, add -ol. 3. Hydroxyl groups take precedent over alkyl groups and halogens. Q1
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Ch221 Gorman Lecture Notes, Chapter 4 p. 2 of 12 OH OH Radicofunctional trans-2-methylcyclopentyl alcohol 1-ethylpropyl alcohol Substituitive trans-2-methylcyclopentanol 3-pentanol III. CLASSES OF ALCOHOLS AND ALKYL HALIDES OH I Tertiary (3°) Secondary (1°) Primary ( VERY IMPORTANT FOR REACTIVITY Hybridization of the Carbon? The Oxygen? IV. PHYSICAL PROPERTIES Alcohols and alkyl halides have higher BPs than alkanes of similar MW Propane Fluoroethane Ethanol MW = 44 g/mol MW = 44 g/mol MW = 44 g/mol BP = -42 °C BP = -32 ° C BP = 78 °C = 0 D = 1.9 D = 1.7 D F F + - - + O H H O H O H-bonding = 2-12 V. ACIDS AND BASES A. Bronsted and Lowry: Acid is an H+ donor; a Base is an H+ acceptor H A B: - BH A: - Base Acid Conjugate Acid Conjuga Base = ―a little bit of‖ Dipole-dipole forces Figure 4.4 Q2 Q3 NoQ
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Ch221 Gorman Lecture Notes, Chapter 4 p. 3 of 12 H A O:+ A: - Acid Oxonium ion or Hydronium Ion Conjuga Base H :O: H H H H B. Acid Strength 1. Equilibrium expressions HA + H 2 O H 3 O + A - K 3 2 HO A K HA HO [H 2 O] may be treated as a constant and incorporated into a new K called K a Acid Dissociation Constant 3 2 a K K HO HA 2. The pKa unit pK a = -log K a ; K a = 1.8 x 10 -16 ; pK a = 15.7 3. Some general rules to remember: a) Ka increases for strong acids, pK a
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CH04 Instructor Notes - Chapter 4 Alcohols and Alkyl...

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