General Chemistry Principles and Modern Applications 8ed

1. Philip Dutton
University of Windsor, Canada
N9B 3P4
Prentice-Hall © 2002
General Chemistry
Principles and Modern Applications
Petrucci • Harwood • Herring
8th
Edition
Chapter 27: Organic Chemistry

2. Prentice-Hall General Chemistry: Chapter 27Slide 2 of 75
Contents
27-1 Organic Compounds and Structures: An Overview
27-2 Alkanes
27-3 Alkenes and Alkynes
27-4 Aromatic Hydrocarbons
27-5 Alcohols, Phenols, and Ethers
27-6 Aldehydes and Ketones
27-7 Carboxylic Acids and Their Derivatives
27-8 Amines
27-9 Heterocyclic Compounds

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Contents
27-10 Nomenclature of Stereoisomers in Organic Compounds
27-11 An Introduction to Substitution Reactions at
sp3
Hybridized Carbon Atoms
27-12 Synthesis of Organic Compounds
27-13 Polymerization Reactions
Focus On Natural and Synthetic Dyes

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27-1 Organic Compounds and Structures:
An Overview
• Hydrocarbons – the simplest organic compounds.
• Simplest hydrocarbon is methane.

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Ethane

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Skeletal Isomerism
Prentice Hall © 2002 General Chemistry: Chapter 27 Slide 5 of

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Simplified Drawings of Organic Structures

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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.

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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.

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Table 27.1. Some Common Alkyl Groups

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Positional Isomerism

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FunctionalGroups

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27-2 Alkanes

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Conformations

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Ring Structures

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Ring Strain

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Cyclohexane Conformations

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Preparation of Alkanes
CH2=CH2 + H2 → CH3-CH3
Pt
Δ
2 CH3CH2Br + 2 Na → CH3CH2CH2CH3 + 2 NaBr
pressure
Δ

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Reactions of Alkanes
Initiation: Cl-Cl → 2 Cl·
Propagation: H3C-H + Cl· → H3C· + HCl
H3C· + Cl2 → H3C-Cl + Cl·
Termination:
H3C· + Cl·→ H3C-Cl
Cl· + Cl· → Cl-Cl
H3C· + H3C·→ H3C-CH3
Δ or hν

20. Prentice-Hall General Chemistry: Chapter 27Slide 20 of 75
Combustion Reactions
C8H18(l) + O2(g) → 8 CO2(g) + 9 H2O(l)
25
2
ΔH° = -5.48103
J

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Table 27.4 Principle Petroleum Fractions

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Octane Number

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27-3 Alkenes and Alkynes

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Geometric Isomerism

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Elimination Reaction

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Addition Reactions
Markovnikov rule

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Hydration Reaction
Addition is favored in dilute acid and elimination is favored in strong.

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Reduction of C=C

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27-4 Aromatic Hydrocarbons

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Characteristics of Aromatic Hydrocarbons
• Planar (flat) cyclic molecules.
• Conjugated п systems (4n + 2)

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Naming Aromatic Hydrocarbons

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Aromatic Substitution Reactions

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Aromatic Subsitution Reactions

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27-5 Alcohols, Phenols, and Ethers

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Preparation and Use of Alcohols
CO(g) + 2 H2(g) → CH3OH(g)
350 °
C
200 atm
ZnO, Cr2O3

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Preparation and Use of Alcohols
• Methanol.
– 21st
amongst industrial chemicals.
• Ethanol.
– fermentation or by hydration of ethylene.
• Ehylene glycol.
– High boiling point, soluble in water.
• Glycerin.

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Ethers

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Aldehydes and Ketones

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Preparation and Use
• Oxidation of alcohols.
• Extract from natural
sources
• Acetone is extensively
used as a solvent.

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Addition Reactions of the Carbonyl Group

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27-7 Carboxylic Acids and Their
Derivatives

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Oxidation of Alcohols
CH3CH2OH + KMnO4 → CH3CO2
-
K+
→ CH3CO2HOH-
H+

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Aromatic Acids

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Acetyl Group

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Esters

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Amides

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Resonance in Amides

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Reduction Reactions

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Amines

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Preparation of Amines
2 NH3 + CH3Br → CH3NH3
+
Br-
+ NH3 → CH3NH2 + NH4Br

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Basicity of Amines

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Ammonium Salts

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27-9 Heterocyclic Compounds

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27-10 Nomenclature of Stereoisomers in
Organic Compounds

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Chirality

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The R,S System of Nomenclature
Substituent of higher atomic number takes
precedence over one of lower atomic number:

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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:

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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:

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The E,Z System of Nomenclature

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The E,Z System of Nomenclature

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27-11 An Introduction to Substitution
Reactions at sp3
Hybridized Carbon

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SN2 Mechanism
Rate = k[OH-
][CH3Cl]

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Inversion of Configuration

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SN1 Mechanism

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SN1 Mechanism
Rate = k [(CH3)3CCl]

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Racemic Products From SN1 Reactions

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27-12 Synthesis of Organic Compounds

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27-13 Polymerization Reactions

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Table 27.5 Some Polymers Produced by
Chain-Reaction Polymerization

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Condensation Polymerization

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Table 27.6 Some Polymers Produced by
Step Reaction Polymerization

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Stereospecific Polymers

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Focus On Natural and Synthetic Dyes

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Focus On Natural and Synthetic Dyes

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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.