| GENERAL | EXAM I | EXAM II | EXAM III | FINAL EXAM |
The format of the course will be the same as last semester, with a few minor changes:
Quizzes will be on Tuesdays. As last semester you will be allowed to use models, any handouts, and your notes, but not your textbook. There will usually be at least one each week. Again only your best 10 quiz grades will count towards your final grade.
There will on occasion be graded homework assignments. These will typically be assigned on Thursday and be due on the following Tuesday.
We will be a little more formal and structured in the presentation of the learning group problems. We will continue to use these for review before exams, but we will talk more beforehand about how to present the material.
Some suggestions:
Review nomenclature using the Nameit program, 1979 version.
Work more problems
Come and talk to me more.
Update your set of index cards as we encounter each new reaction.
Check out the “Organic Rx Mechanism” program on the Math & Science
menu; it illustrates a variety of mechanisms with which you should be familiar.
Also try the “Organic Chem GRE Drill” program; it’s a multiple-choice
predict the product drill.
Our exam and lecture schedule for the spring semester is as follows (dates, times and places for the exams will be announced):
Chapter 8 Alkenes and Alkynes II: Addition Reactions
Chapter 10 Radical Reactions
Chapter 11 Alcohols and Ethers
Chapter 12 Alcohols from Carbonyl Compounds. Oxidation-Reduction
and Organometallic Compounds
Exam I: Week of February 18
Chapter 13 Conjugated Unsaturated Systems
Chapter 14 Aromatic Compounds
Chapter 15 Reactions of Aromatic Compounds
Exam II: Week of March 25.
Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to
a Carbonyl Group
Chapter 17 Aldehydes and Ketones II. Aldol Reactions
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic
Addition-Elimination at the Acyl Carbon
Exam III: Week of April 22.
Chapter 19 Synthesis and Reactions of ?-Dicarbonyl Compounds: More Chemistry of Enolate Ions
Final Exam: Friday May 10; 1:30 PM.
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SPRING 2002
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Chapter 8 Alkenes and Alkynes II: Addition Reactions
8.1 Introduction: Additions to Alkenes
8.2 Addition of Hydrogen Halides to Alkenes: Markovnikov’s Rule
8.3 Stereochemistry of the Ionic Addition to an Alkene
8.4 Addition of Sulfuric Acid to Alkenes
8.5 Addition of Water to Alkenes: Acid-Catalyzed Hydration
8.6 Addition of Bromine and Chlorine to Alkenes
8.7 Stereochemistry of the Addition of Halogens to Alkenes
8.10 Oxidations of Alkenes: Syn Hydroxylations
8.11 Oxidative Cleavage of Alkenes
8.14 Oxidative Cleavage of Alkynes
(review Ch. 7, sections 11 – 16)
8.15 Synthetic Strategies Revisited
Chapter 10 Radical Reactions
10.1 Introduction
10.2 Homolytic Bond Dissociation Energies
10.3 The Reactions of Alkanes with Halogens
10.4 Chlorination of Methane: Mechanism of Reaction
10.5 Chlorination of Methane: Energy Changes
10.6 Halogenation of Higher Alkanes
10.7 The Geometry of Alkyl Radicals
10.8 Reactions that Generate Tetrahedral Stereocenters
10.9 Radical Addition to Alkenes: The Anti-Markovnikov Addition of
Hydrogen Bromide
10.10 Radical Polymerization of Alkenes: Chain-Growth polymers
10.11 Other Important Radical Reactions
Chapter 11 Alcohols and Ethers
11.1 Structure and Nomenclature
11.2 Physical Properties of Alcohols and Ethers
11.3 Important Alcohols and Ethers
11.4 Synthesis of Alcohols from Alkenes
11.5 Alcohols from Alkenes through Oxymercuration-Demercuration
11.6 Hydroboration: Synthesis of Organoboranes
11.7 Alcohols from Alkenes through Hydroboration-Oxidation
11.8 Reactions of Alcohols
11.9 Alcohols as Acids
11.10 Conversion of Alcohols into Mesylates and Tosylates
11.11 Mesylates and Tosylates in SN2 Reactions
11.12 Conversion of Alcohols into Alkyl Halides
11.13 Alkyl Halides from the Reaction of Alcohols with Hydrogen Halides
11.14 Alkyl Halides from the Reaction of Alcohols with PBr3 or SOCl2
11.15 Synthesis of Ethers
11.16 Reactions of Ethers
11.17 Epoxides
11.18 Reactions of Epoxides
11.19 Anti Hydroxylation of Alkenes via Epoxides
11.21 Summary of Reactions of Alkenes, Alcohols, and Ethers
Chapter 12 Alcohols from Carbonyl Compounds. Oxidation-Reduction and Organometallic Compounds
12.1 Introduction
12.2 Oxidation-Reduction Reactions in Organic Chemistry
12.3 Alcohols by Reduction of Carbonyl Compounds
12.4 Oxidation of Alcohols
12.5 Organometallic Compounds
12.6 Preparation of Organolithium and Organomagnesium Compounds
12.7 Reactions of Organolithium and Organomagnesium Compounds
12.8 Alcohols from Grignard Reagents
12.10 Protecting Groups
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Chapter 13 Conjugated Unsaturated Systems
13.1 Introduction
13.2 Allylic Substitution and the Allyl radical
13.3 The Stability of the Allyl radical
13.4 The Allyl Cation
13.5 Summary of Rules for Resonance
13.6 Alkadienes and Polyunsaturated Hydrocarbons
13.7 1,3-Butadiene: Electron Delocalization
13.8 The Stability of Conjugated Dienes
13.9 Ultraviolet-Visible Spectroscopy
13.10 Electrophilic Attack on Conjugated Dienes: 1,4-Addition
13.11 The Diels-Alder Reaction: A 1,4-Cycloaddition Reaction of Dienes
Chapter 14 Aromatic Compounds
14.1 Introduction
14.2 Nomenclature of Benzene Derivatives
14.3 Reactions of Benzene
14.4 The Kekule Structure for Benzene
14.5 The Stability of Benzene
14.6 Modern Theories of the Structure of Benzene
14.7 Huckel’s Rule: The (4n+2) ? Electron Rule
14.8 Other Aromatic Compounds
14.9 Heterocyclic Aromatic Compounds
14.11 Spectroscopy of Aromatic Compounds
Chapter 15 Reactions of Aromatic Compounds
15.1 Electrophilic Aromatic Substitution Reactions
15.2 A General Mechanism for Electrophilic Aromatic Substitution :
Arenium Ions
15.3 Halogenation of Benzene
15.4 Nitration of Benzene
15,5 Sulfonation of Benzene
15.6 Friedel-Crafts Alkylation
15.7 Friedel-Crafts Acylation
15.8 Limitations of Friedel-Crafts Reactions
15.9 Synthetic Applications of Friedel-Crafts Acylations: The Clemmensen
Reduction
15.10 Effect of Substituents on Reactivity and Orientation
15.11 Theory of Substituent Effects on Electrophilic Aromatic Substitution
20.3 Basicity of Amines: Amine Salts
21.5 Reactions of Phenols as Acids
21.8 Reactions of the Benzene Ring of Phenols
15.12 Reactions of the Side Chain of Alkylbenzenes
15.13 Alkenylbenzenes
15.14 Synthetic Applications
20.5B Preparation of Aromatic Amines through Reduction of Nitro Compounds
20.7 Reactions of Amines with Nitrous Acid
20.8 Replacement Reactions of Arenediazonium Salts
15.15 Allylic and Benzylic Halides in Nucleophilic Substitution Reactions
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Chapter 16 Aldehydes and Ketones I. Nucleophilic Addition to a Carbonyl Group
16.1 Introduction
16.2 Nomenclature of Aldehydes and Ketones
16.3 Physical Properties
16.4 Synthesis of Aldehydes
16.5 Synthesis of Ketones
16.6 Nucleophilic Addition to the Carbon-Oxygen Double Bond
16.7 The Addition of Alcohols: Hemiacetals and Acetals
16.8 The Addition of Derivatives of Ammonia
20.5C Preparation of Primary, Secondary, or Tertiary Amines through
Reductive Amination
16.9 The Addition of Hydrogen Cyanide
16.10 The Addition of Ylides: The Wittig Reaction
16.14 Spectroscopic Properties of Aldehydes and Ketones
Chapter 17 Aldehydes and Ketones II. Aldol Reactions
17.1 The Acidity of ? Hydrogens of Carbonyl Compounds: Enolate Anions
17.2 Keto and Enol Tautomers
17.3 Reactions via Enols and Enolate Anions
17.4 The Aldol Reaction: The Addition of Enolate Anions to Aldehydes
and Ketones
17.5 Crossed Aldol Reactions
17.6 Cyclizations via Aldol Condensations
17.7 Lithium Enolates
17.9 Additions to ???-Unsaturated Aldehydes and Ketones
Chapter 18 Carboxylic Acids and Their Derivatives. Nucleophilic Addition-Elimination at the Acyl Carbon
18.1 Introduction
18.2 Nomenclature and Physical Properties
18.3 Preparation of Carboxylic Acids
18.4 Nucleophilic Addition-Elimination at the Acyl Carbon
18.5 Acyl Chlorides
18.6 Carboxylic Acid Anhydrides
18.7 Esters
18.8 Amides
18.11 Decarboxylation of Carboxylic Acids
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Chapter 19 Synthesis and Reactions of ?-Dicarbonyl Compounds: More Chemistry of Enolate Ions
19.1 Introduction
19.2 The Claisen Condensation: The Synthesis of ?-Keto Esters
19.3 The Acetoacetic Ester Synthesis: Synthesis of Methyl Ketones (Substituted
Acetones)
19.4 The Malonic Ester Synthesis: Synthesis of Substituted Acetic Acids
18.11 Decarboxylation of Carboxylic Acids
19.5 Further Reactions of Active Hydrogen Compounds
19.6 Direct Alkylation of Esters and Nitriles
19.8 The Knoevenagel Condensation
17.9 Additions to a,b-Unsaturated Aldehydes and Ketones
19.9 Michael Additions