Chem 164/261 - Lecture Outline & Assignment #4
Readings:
Organic Chemistry, L Wade, UA Custom Edition, 2013, Volume 1 (Chem 164/261)
• Functional Group List - Inside Front Cover (also Handout)
• Chapter 8 – Structure and Synthesis of Alkenes
• Chapter 9 – Reactions of Alkenes
• Chapter 10 - Alkynes
Problems:
Do Not turn in, answers available in "Student Solutions Manual for Organic Chemistry" for LG Wade
(do all “solved problems” in chapters listed below)
• Chapter 8: 8.1 to 8.11; 8.13 to 8.25; 8.31 to 8.33; 8.40; 8.53; 8.54
• Chapter 9: 9.1 to 9.4; 9.6; 9.10; 9.11; 9.13; 9.15; 9.17 to 9.19; 9.23; 9.24; 9.29; 9.34; 9.37; 9.40; 9.47; 9.49; 9.63
• Chapter 10: 10.1; 10.5; 10.7; 10.12; 10.20; 10.21; 10.23; 10.26 to 10.29; 10.32
Lecture Outline 4:
Alkenes and Alkynes – Addition and Elimination Reactions
I. Structure and Nomenclature
A. Alkenes with one double bond
1. Nomenclature
2. Orbital Hybridization
3. Stereoisomerism - cis, trans, and Z, E.
4. Cycloalkenes
B. Polyenes
C. Alkynes
1. Nomenclature
2. Structure and Orbital Hybridization
II. Physical Properties and Sources
A. Physical Properties - solubility, density, BP, MP
B. Occurrence of Alkenes and Alkynes
C. Terpenes and Isoprene Units
III. Reactions of Multiple Bonds between Carbons
A. General Characteristics - Addition Reactions, electrophiles and nucleophiles
1. Arrow Conventions for Mechanisms
B. Addition Reactions of Alkenes - Stereospecificity
1. Hydrogenation
2. Halogenation
3. Halohydrin Formation
4. Hydrogen Halide Addition – Markovnikov’s Rule
5. Water Addition - Alcohol synthesis
6. Alcohol Addition - Ether synthesis
7. Mercuration - Demercuration
8. Hydroboration - Oxidation
9. Hydroboration and Treatment with Acid
C. Oxidation of Alkenes
1. Ozonolysis
2. Osmium Tetroxide and Potassium Permanganate
3. Epoxidation
D. Addition Reactions of Alkynes
1. Hydrogenation
2. Halogenation
3. Hydrogen Halide Addition
4. Hydration - aldehyde and ketone synthesis - tautomers
a) Markovnikov Addition of Water
b) Hydroboration - Oxidation
E. Oxidation of Alkynes
1. Ozonolysis
2. Potassium Permanganate
IV. Synthesis of Alkenes and Alkynes - Eliminations
A. Elimination Reactions
1. El Mechanism - Saytzeff Rule, Leaving Groups
2. E2 Mechanism - Stereochemistry
B. Synthesis of Alkenes and Alkynes
1. Dehydrohalogenation
2. Dehalogenation of vic - dihalides
3. Dehydration of alcohols
C. Hydrogenation - Dehydrogenation
D. Replacement of Acetylenic Hydrogen
1. Acidity of Alkynes
2. Alkylation - Substitution Reactions
3. Coupling of Acetylenes
V. Polymerization and Radical Reactions of Alkenes
A. Radical Additions
1. Hydrogen Halide Addition
2. Addition of Alkyl Radicals
B. Polymers and Polymerization
1. Polyethylene and General Mechanism
2. Other types of Polymers - Nomenclature and Properties
