Section 13: Mass Spectrometry
Instructor's Notes for Section 13
Mass Spectrometry, Mass Spectrometry (Mass Spec) Principles, A Normal Mass Spectrum
Importance of Determining the Molar Masses in Molecular Formula, Isotope Ratios, the M+1 and the M+2 Peaks
Analyze the atom isotopes given
Nitrogen Rule, Making the Molecular Ion (M+)
Four Types of Fragmentations 1) Loss of Water 2) Direct Hit on a σ Bond
Example of Direct Hit on a σ Bond (For Alkanes), Example of Direct Hit on a σ Bond (Benzylic Cleavage)
Four Types of Fragmentations cont. - 3) α-Cleavage
Alpha cleavage (with Aldehydes, Ketones and Carboxylic acids)
Mass Spec Fragmentation Examples
Predicting Fragmentation Patterns
Four Types of Fragmentations cont. – 4) McLafferty Rearrangment
Infrared Spectroscopy, Interaction of Electromagnetic Radiation(hν) with Molecules, Spectroscopy Theory, The Electromagnetic Spectrum,
IR Table
IR Spectrum Regions
Hydrogen Region (3550-2700 cm-1), Triple Bond Region (2300-2100 cm-1), Double Bond Region (1850-1350 cm-1), Specific Carbonyl Positions for Different Functional Groups, Fingerprint Region (1300-500 cm-1)
Interpreting IR Spectra by Functional Groups Part 1
Interpreting IR Spectra by Functional Groups Part 2
Interpreting IR Spectra by Functional Groups Part 3
Ultraviolet-Visible Spectroscopy, Definitions, Examples UV Spectrum, Lambert-Beer Law, Types of Electronic Transitions (from s, p, and NB orbitals)
Energy Diagram Examples, Probable Absorptions
Visible Region Colors, Determining Structure in the UV-Visible Spectroscopy Region
Practice Homework for Section 13
Practice Homework for Section 13 (Key)
Quiz for Section 13
Quiz for Section 13 (Key)
Section 17: Reactions of the Alpha-Carbon
Instructor's Notes for Section 17
Keto-Enol Tautomerism - Acidic and Basic Conditions
Reactivity of Enols: Alpha-Substitution Reactions, General Mechanism of Addition to Enols, Alpha Halogenation of Aldehydes and Ketones
Elimination Reactions of alpha-Bromoketones, Worked Example
Alpha Bromination of Carboxylic Acids - Hell–Volhard–Zelinskii reaction, Worked Example
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation – Part 1
Acidity of Alpha Hydrogen Atoms: Enolate Ion Formation – Part 2
Table - Acidity Constants for Some Organic Compounds
Alkylation of Enolate Ions, Constraints on Enolate Alkylation
Thermodynamic vs Kinetic Enolates
Malonic Ester Synthesis, Formation of Enolate and Alkylation, Dialkylation
Hydrolysis and Decarboxylation, Decarboxylation of beta-Ketoacids
Overall Conversion
Worked Example
Acetoacetic Ester Synthesis, Acetoacetic Ester (Ethyl Acetoacetate), Generalization: beta-Keto Esters
Direct Alkylation of Ketones, Esters, and Nitriles – Part 1
Direct Alkylation of Ketones, Esters, and Nitriles – Part 2
Alkylating and Acylating via an Enamine Intermediate
Aldol Reaction, Aldol Condensation
Characteristics of the Aldol Condensation
Ester Condensations, Dieckmann Condensation
Mixed Ester Condensations, Dianion Nucleophiles
Conjugate Additions of Enolates - aka Michael Reaction
Michael + Aldol = Robinson Annulation
Practice Homework for Section 17
Practice Homework for Section 17 (Key)
Quiz for Section 17
Quiz for Section 17 (Key)
Section 18: Reactions of Benzene and Substituted Benzenes
Instructor's Notes for Section 18
Electrophilic Aromatic Substitution
Hammond Postulate, Electrophilic Aromatic Substitution: Nitration
Effect of Substituents
Effect of Substituents: EDG by Resonance, Effect of Substituents: EWG (Deactivation), Effect of Substituents: Halides (ortho-, para- Deactivating)
Table 1. Effect of Substituents on Electrophilic Aromatic Substitution, Steric Factors: ortho- vs para-, Multiple Substituents Effects
Nitration, Nitration Examples, Protecting Group Chemistry
Halogenation, Highly Activated Aromatic Rings
Sulfonation, Mechanism, and Desulfonation: Sulfonation is Reversible
Friedel-Crafts Alkylation, Friedel-Crafts Alkylation Mechanism, Other Carbocation Forming Sources, Examples of Friedel-Crafts Alkylation
Friedel-Crafts Acylation, Mechanism, Examples of Friedel-Crafts Acylation
Nucleophilic Aromatic Substitution: Diazonium Ions
Additional Useful Reactions, Reduction Examples
More Useful Reactions
Summary of Reactions Known Up to this Point
Nucleophilic Aromatic Substitution: Addition-Elimination, Nucleophilic Aromatic Substitution: Addition-Elimination Examples
Nucleophilic Aromatic Substitution: Elimination - Addition, Nucleophilic Aromatic Substitution: Elimination – Addition Examples
EAS Total Synthesis Problems – Part 1
EAS Total Synthesis Problems – Part 2
For Activated Phenols and Anilines Use Protection Chemistry, EAS Total Synthesis Problems
Practice Homework for Section 18
Practice Homework for Section 18 (Key)
Quiz for Section 18
Quiz for Section 18 (Key)

Hydrogen Region (3550-2700 cm-1), Triple Bond Region (2300-2100 cm-1), Double Bond Region (1850-1350 cm-1), Specific Carbonyl Positions for Different Functional Groups, Fingerprint Region (1300-500 cm-1)

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