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Topics
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Topic
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Subtopics
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Objectives
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1
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Structure and Bonding
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- The Periodic Table
- Bonding
- Lewis Structures
- Isomers
- Exceptions to the Octet Rule
- Resonance
- Determining Molecular Shape
- Drawing Organic Structures
- Hybridization
- Ethane, Ethylene, and Acetylene
- Bond Length and Bond Strength
- Electronegativity and Bond Polarity
- Polarity of Molecules
- Oxybenzone–A Representative Organic Molecule
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- Drawing a valid Lewis structure; example: CH3CHO
- Calculating formal charge
- Predicting geometry from a valid Lewis structure
- Identifying isomers and resonance structures
- Using curved arrows
- Predicting hybridization from a valid Lewis structure
- Determining if a molecule has a net dipole from a valid Lewis structure; example: CH3OH
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2
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Introduction to Organic Molecules and Functional Groups
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- Functional Groups
- An Overview of Functional Groups
- Intermolecular Forces
- Physical Properties
- Application: Vitamins
- Application of Solubility: Soap
- Application: The Cell Membrane
- Functional Groups and Reactivity
- Biomolecules
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- Predicting boiling points
- Determining sites of hydrogen bonding between two identical molecules
- Determining sites of hydrogen bonding between an organic molecule and H2O
- Drawing curved arrows to show the reaction between a nucleophile and an electrophile
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3
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Alkanes
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- Alkanes—An Introduction
- Cycloalkanes
- An Introduction to Nomenclature
- Naming Alkanes
- Naming Cycloalkanes
- Natural Occurrence of Alkanes
- Properties of Alkanes
- Conformations of Acyclic Alkanes—Ethane
- Conformations of Butane
- An Introduction to Cycloalkanes
- Cyclohexane
- Substituted Cycloalkanes
- Oxidation of Alkanes
- Lipids—Part 1
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- Naming an alkane using the IUPAC system
- Naming a cycloalkane using the IUPAC system
- Determining the highest and lowest energy conformations using Newman projections
- Drawing two conformations for a disubstituted cyclohexane
- Determining whether a compound is oxidized or reduced
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4
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Stereochemistry
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- Starch and Cellulose
- The Two Major Classes of Isomers
- Looking Glass Chemistry—Chiral and Achiral Molecules
- Stereogenic Centers
- Stereogenic Centers in Cyclic Compounds
- Labeling Stereogenic Centers with R or S
- Diastereomers
- Meso Compounds
- R and S Assignments in Compounds with Two or More Stereogenic Centers
- Disubstituted Cycloalkanes
- Isomers—A Summary
- Physical Properties of Stereoisomers
- Chemical Properties of Enantiomers
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- Locating stereogenic centers
- Labeling stereogenic centers with R or S
- Assigning R or S when the lowest-priority group is not oriented toward the back
- Finding and drawing all stereoisomers for a compound with two stereogenic centers
- Determining if two non identical compounds are constitutional isomers, enantiomers, or diastereomers
- Calculations involving enantiomeric excess
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5
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Understanding Organic Reactions
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- Writing Equations for Organic Reactions
- Kinds of Organic Reactions
- Bond Breaking and Bond Making
- Bond Dissociation Energy
- Thermodynamics
- Enthalpy and Entropy
- Energy Diagrams
- Energy Diagram for a Two-Step Reaction Mechanism
- Kinetics
- Catalysts
- Enzymes
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- Using full-headed curved arrows to show the movement of electron pairs
- Using half-headed curved arrows to show the movement of single electrons
- Calculating ΔHo of a reaction
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6
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Alkyl Halides and Nucleophilic Substitution
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- Introduction to Alkyl Halides
- Nomenclature
- Properties of Alkyl Halides
- Interesting Alkyl Halides
- The Polar Carbon–Halogen Bond
- General Features of Nucleophilic Substitution
- The Leaving Group
- The Nucleophile
- The Mechanisms for Nucleophilic Substitution
- The SN2 Mechanism
- The SN1 Mechanism
- Carbocation Stability
- The Hammond Postulate
- When Is the Mechanism SN1 or SN2?
- Biological Nucleophilic Substitution
- Vinyl Halides and Aryl Halides
- Organic Synthesis
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- Comparing the nucleophile and leaving group to determine if products are favored
- Drawing the product(s) of an Sn2 reaction
- Drawing the product(s) of an Sn1 reaction
- Deciding if a reaction proceeds by Sn1 or Sn2
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7
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Alkyl Halides and Elimination Reactions
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- Alkyl Halides and Elimination Reactions
- General Features of Elimination
- Alkenes—The Products of Elimination Reactions
- The Mechanisms of Elimination
- The E2 Mechanism
- The Zaitsev Rule
- Stereochemistry of the E2 Reaction
- The E1 Mechanism
- SN1 and E1 Reactions
- When Is the Mechanism E1 or E2?
- E2 Reactions and Alkyne Synthesis
- When Is the Reaction SN1, SN2, E1, or E2?
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- Comparing the stability o f alkenes
- Drawing all products and predicting the major product of an elimination reaction
- Drawing the product of an E2 reaction of a halo-cyclohexane when loss of HX must be anti periplanar
- Deciding if a β elimination reaction proceeds by an E1 or E2 mechanism
- Deciding if a reaction proceeds by SN1, SN2, E1, or E2
- Drawing the product(s) of a reaction with a 1° alkyl halide
- Drawing the product(s) of a reaction with a 2° alkyl halide
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8
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Alkenes and Addition Reactions
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- Calculating Degrees of Unsaturation
- Nomenclature
- Properties of Alkenes
- Interesting Alkenes
- Lipids—Part 2
- Preparation of Alkenes
- Introduction to Addition Reactions
- Hydrohalogenation—Electrophilic Addition of HX
- Markovnikov’s Rule
- Stereochemistry of Electrophilic Addition of HX
- Hydration—Electrophilic Addition of Water
- Halogenation—Addition of Halogen
- Stereochemistry of Halogenation
- Halohydrin Formation
- Hydroboration–Oxidation
- Keeping Track of Reactions
- Alkenes in Organic Synthesis
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- Calculating degrees of unsaturation
- Assigning E,Z in naming an alkene
- Drawing the products of an addition reaction
- Comparing the products of hydration of an alkene
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9
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Alkynes and Synthesis
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- Nomenclature
- Properties of Alkynes
- Interesting Alkynes
- Preparation of Alkynes
- Introduction to Alkyne Reactions
- Addition of Hydrogen Halides
- Addition of Halogen
- Addition of Water
- Hydroboration–Oxidation
- Reaction of Acetylide Anions
- Synthesis
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- Converting an alkene to an alkyne
- Drawing the product of an addition reaction
- Converting an enol to a keto tautomer in acid
- Converting a keto tautomer to an enol in acid
- Comparing the products of hydration of an alkyne
- Comparing reactions of acetylide anions
- Devising a synthesis
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10
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Spectroscopy
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- Mass Spectrometry and the Molecular Ion
- Alkyl Halides and the M + 2 Peak
- Fragmentation
- Fragmentation Patterns of Some Common Functional Groups
- Other Types of Mass Spectrometry
- Electromagnetic Radiation
- The General Features of Infrared Spectroscopy
- IR Absorptions
- Infrared Spectra of Common Functional Groups
- IR and Structure Determination
- An Introduction to NMR Spectroscopy
- 1H NMR: Number of Signals
- 1H NMR: Position of Signals
- The Chemical Shifts of Protons on sp2 and sp Hybridized Carbons
- 1H NMR: Intensity of Signals
- 1H NMR: Spin–Spin Splitting
- Spin–Spin Splitting in Alkenes
- Using 1H NMR to Identify an Unknown
- 13C NMR Spectroscopy
- Magnetic Resonance Imaging (MRI)
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- Proposing possible molecular formulas for a compound that contains C, H, and perhaps O with a given molecular ion (A.1)
- Determining the molecular ions for a compound with Cl or Br (A.2); example: bromocyclohexane (C6H11Br)
- Proposing possible structures for fragmentation by α cleavage
- Using the functional groups to distinguish two compounds by IR spectroscopy
- Using IR absorptions to distinguish between two compounds
- Using MS and IR to determine possible structures of a compound that contains C,H, and O
- Calculating the chemical shift of an absorption that occurs at 1000 Hz downfield from TMS using a 400 MHz NMR spectrometer
- Determining the different types of protons in a compound; example: 1,4-dichlorobutane
- Determining equivalency in a cycloalkane
- Determining which protons absorb further downfield; two factors
- Determining the 1H NMR integration ratio for a compound
- Determining the splitting pattern for a molecule using the n+1 rule
- Determining the number of peaks present in the 1H NMR signal of an alkene using the (n+1)(m+1) rules
- Determining splitting patterns when an absorbing proton has nonequivalent protons on two adjacent carbs
- Using a molecular formula and 1H NMR data to determine a structure
- Determining the different types of C atoms in a compound
- Determining which C atom absorbs further downfield
- Using a molecular formula, IR, 1H NMR, and 13C NMR for structure determination
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11
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Final Exam
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