Download presentation
Presentation is loading. Please wait.
Published byGavin Sutton Modified over 9 years ago
1
Philip Dutton University of Windsor, Canada N9B 3P4 Prentice-Hall © 2002 General Chemistry Principles and Modern Applications Petrucci Harwood Herring 8 th Edition Chapter 27: Organic Chemistry
2
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 2 of 75 Contents 27-1Organic Compounds and Structures: An Overview 27-2Alkanes 27-3Alkenes and Alkynes 27-4Aromatic Hydrocarbons 27-5Alcohols, Phenols, and Ethers 27-6Aldehydes and Ketones 27-7Carboxylic Acids and Their Derivatives 27-8Amines 27-9Heterocyclic Compounds
3
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 3 of 75 Contents 27-10Nomenclature of Stereoisomers in Organic Compounds 27-11An Introduction to Substitution Reactions at sp 3 Hybridized Carbon Atoms 27-12Synthesis of Organic Compounds 27-13Polymerization Reactions Focus On Natural and Synthetic Dyes
4
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 4 of 75 27-1 Organic Compounds and Structures: An Overview Hydrocarbons – the simplest organic compounds. Simplest hydrocarbon is methane.
5
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 5 of 75 Ethane
6
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 6 of 75 Skeletal Isomerism Prentice Hall © 2002 General Chemistry: Chapter 27 Slide 5 of
7
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 7 of 75 Simplified Drawings of Organic Structures
8
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 8 of 75 Nomenclature Select the longest continuous carbon chain. –This determines the base name. Consider each branch and name similarly except change the name from –ane to –yl. Number the C atoms so that substituents have the lowest possible number.
9
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 9 of 75 Nomenclature Name each substituent according to its identity and the number of the C atom to which it is attached. –Use di, tri, tetra as appropriate. Separate numbers from one another by commas. List substituents alphabetically by name.
10
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 10 of 75 Table 27.1. Some Common Alkyl Groups
11
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 11 of 75 Positional Isomerism
12
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 12 of 75 Functional Groups
13
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 13 of 75 Functional Groups
14
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 14 of 75 27-2 Alkanes
15
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 15 of 75 Conformations
16
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 16 of 75 Ring Structures
17
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 17 of 75 Ring Strain
18
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 18 of 75 Cyclohexane Conformations
19
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 19 of 75 Preparation of Alkanes CH 2 =CH 2 + H 2 → CH 3 -CH 3 Pt Δ 2 CH 3 CH 2 Br + 2 Na → CH 3 CH 2 CH 2 CH 3 + 2 NaBr pressure Δ
20
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 20 of 75 Reactions of Alkanes Initiation:Cl-Cl → 2 Cl· Propagation:H 3 C-H + Cl· → H 3 C· + HCl H 3 C· + Cl 2 → H 3 C-Cl + Cl· Termination: H 3 C· + Cl· → H 3 C-Cl Cl· + Cl· → Cl-Cl H 3 C· + H 3 C· → H 3 C-CH 3 Δ or h
21
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 21 of 75 Combustion Reactions C 8 H 18 (l) + O 2 (g) → 8 CO 2 (g) + 9 H 2 O(l) 25 2 ΔH° = -5.48 10 3 J
22
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 22 of 75 Table 27.4 Principle Petroleum Fractions
23
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 23 of 75 Octane Number
24
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 24 of 75 27-3 Alkenes and Alkynes
25
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 25 of 75 Geometric Isomerism
26
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 26 of 75 Elimination Reaction
27
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 27 of 75 Addition Reactions Markovnikov rule
28
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 28 of 75 Hydration Reaction Addition is favored in dilute acid and elimination is favored in strong.
29
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 29 of 75 Reduction of C=C
30
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 30 of 75 27-4 Aromatic Hydrocarbons
31
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 31 of 75 Characteristics of Aromatic Hydrocarbons Planar (flat) cyclic molecules. Conjugated п systems (4n + 2)
32
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 32 of 75 Naming Aromatic Hydrocarbons
33
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 33 of 75 Aromatic Substitution Reactions
34
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 34 of 75 Aromatic Subsitution Reactions
35
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 35 of 75 27-5 Alcohols, Phenols, and Ethers
36
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 36 of 75 Preparation and Use of Alcohols CO(g) + 2 H 2 (g) → CH 3 OH(g) 350 ° C 200 atm ZnO, Cr 2 O 3
37
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 37 of 75 Preparation and Use of Alcohols Methanol. –21 st amongst industrial chemicals. Ethanol. –fermentation or by hydration of ethylene. Ehylene glycol. –High boiling point, soluble in water. Glycerin.
38
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 38 of 75 Ethers
39
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 39 of 75 Aldehydes and Ketones
40
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 40 of 75 Preparation and Use Oxidation of alcohols. Extract from natural sources Acetone is extensively used as a solvent.
41
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 41 of 75 Addition Reactions of the Carbonyl Group
42
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 42 of 75 27-7 Carboxylic Acids and Their Derivatives
43
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 43 of 75 Oxidation of Alcohols CH 3 CH 2 OH + KMnO 4 → CH 3 CO 2 - K + → CH 3 CO 2 H OH - H+H+
44
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 44 of 75 Aromatic Acids
45
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 45 of 75 Acetyl Group
46
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 46 of 75 Esters
47
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 47 of 75 Amides
48
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 48 of 75 Resonance in Amides
49
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 49 of 75 Reduction Reactions
50
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 50 of 75 Amines
51
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 51 of 75 Preparation of Amines 2 NH 3 + CH 3 Br → CH 3 NH 3 + Br - + NH 3 → CH 3 NH 2 + NH 4 Br
52
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 52 of 75 Basicity of Amines
53
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 53 of 75 Ammonium Salts
54
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 54 of 75 27-9 Heterocyclic Compounds
55
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 55 of 75 27-10 Nomenclature of Stereoisomers in Organic Compounds
56
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 56 of 75 Chirality
57
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 57 of 75 The R,S System of Nomenclature Substituent of higher atomic number takes precedence over one of lower atomic number:
58
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 58 of 75 The R,S System of Nomenclature If two substituents attached to the stereocenter have the same priority, proceed along the chains to the first point of difference:
59
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 59 of 75 The R,S System of Nomenclature Double and triple bonds count as if they were single and the atoms are duplicated or triplicated at the other end of the double or triple bond:
60
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 60 of 75 The E,Z System of Nomenclature
61
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 61 of 75 The E,Z System of Nomenclature
62
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 62 of 75 27-11 An Introduction to Substitution Reactions at sp 3 Hybridized Carbon
63
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 63 of 75 S N 2 Mechanism Rate = k[OH - ][CH 3 Cl]
64
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 64 of 75 Inversion of Configuration
65
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 65 of 75 S N 1 Mechanism
66
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 66 of 75 S N 1 Mechanism Rate = k [(CH 3 ) 3 CCl]
67
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 67 of 75 Racemic Products From S N 1 Reactions
68
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 68 of 75 27-12 Synthesis of Organic Compounds
69
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 69 of 75 27-13 Polymerization Reactions
70
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 70 of 75 Table 27.5 Some Polymers Produced by Chain-Reaction Polymerization
71
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 71 of 75 Condensation Polymerization
72
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 72 of 75 Table 27.6 Some Polymers Produced by Step Reaction Polymerization
73
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 73 of 75 Stereospecific Polymers
74
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 74 of 75 Focus On Natural and Synthetic Dyes
75
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 75 of 75 Focus On Natural and Synthetic Dyes
76
Prentice-Hall © 2002General Chemistry: Chapter 27Slide 76 of 75 Chapter 27 Questions Develop problem solving skills and base your strategy not on solutions to specific problems but on understanding. Choose a variety of problems from the text as examples. Practice good techniques and get coaching from people who have been here before.
Similar presentations
© 2025 SlidePlayer.com. Inc.
All rights reserved.