We’ll begin OCHEM II with spectroscopy and we will introduce concepts of mass spec. We will learn how to interpret mass spec fragments and how to predict fragmentation of molecules. You will also learn how to interpret infrared and UV-vis spectroscopy.

• 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) Alpha Cleavage
• Alpha cleavage (with Aldehydes, Ketones and Carboxylic acids)
• Mass Spec Fragmentation Examples
• Predicting Fragmentation Patterns
• Four Types of Fragmentations cont. – 4) McLafferty Rearrangement
• Infrared Spectroscopy, Interaction of Electromagnetic Radiation (hv) 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

Our next stop leads to interpreting NMR spectroscopy.  This section will teach you how to analyze ¹H NMR and ¹³C NMR, and how to elucidate unknown molecules and predict with exact precision the chemical structure.

• Nuclear Magnetic Resonance (NMR)
• The Chemical Shift, The Chemical Shift, – Downfield Absorptions, – Inductive Effects, – pi Electron Effects
• Chemically Equivalent H, Table with NMR Shifts
• Assigning NMR Splittings – A Story of Balconies
• Calculating Chemical Shifts – Part 1
• Calculating Chemical Shifts – Part 2
• Integration, Spin Coupling, 
• Predicting Double Bond Proton Signals
• Aromatic Coupling
• Interpreting ¹H NMR Spectra, Example 1
• Interpreting ¹H NMR Spectra, Example 2
• ¹³C (Carbon-13) NMR, ¹³C NMR Examples
• DEPT ¹³C NMR – Distortional Enhancement by Polarization Transfer
• Solving NMR Spectra – Example 1
• Solving NMR Spectra – Example 2
• Solving NMR Spectra – Example 3
• Solving NMR Spectra – Example 4

This section is the beginning of a series of synthesis and reactions of carbonyl containing compounds. You will become an expert at naming carboxylic acids and its derivatives.  Here, you will learn synthesis and reactions, hydrolysis and reductions of the carbonyl group.

• Naming Carboxylic Acids and Esters
• Naming Carboxylic Acids, Aldehydes, Ketones, and Carbonyl Group Containing Molecules: When Attached to a Ring
• Advanced Nomenclature, Multiple Functional Groups
• Carboxylic Acid Derivatives, Benzoic Acid Derivatives
• Practice:  Multiple Functional Groups Part 1
• Practice:  Multiple Functional Groups Part 2
• Substitution at Carbonyl Groups (C=O), Factors for Substitution Rate and Product Equilibrium, and Reactivity of Carbonyl Compounds
• Preparation of Acyl Chlorides, and Reactions of Acyl Chlorides
• Preparation of Anhydrides, Anhydride Synthesis
• Preparation of Esters (3 ways)
• Preparation of Carboxylic Acids
• Saponification
• Amide Hydrolysis, Nitrile Hydrolysis
• Nitrile Hydrolysis and Saponification
• Complete the Following Syntheses, Preparation of Amides
• Reactions of LiAlH₄ (with esters, anhydrides and acyl chlorides)
• Reactions of LiAlH₄ (c. acids, aldehyde, ketones, nitriles & amides)
• Reactions of NaBH₄
• Reactions of LiAlH₄, NaBH₄ and H₂/Ni (Recap)

In this section, you will continue learning about the reactivity of the carbonyl group via aldehydes and ketones. As you progress through, you will master the use of different reagents needed for the syntheses and reactions of aldehydes and ketones, plus important name reactions that changed the course of organic chemistry and its applications to biological systems.

• Aldehydes and Ketones
• Preparation of Aldehydes and Ketones
• LiAlH(Ot-Bu)₃ and DIBAL Reactions vs LiAlH₄ and NaBH₄, Catalytic Hydrogenation of Aldehydes and Ketones
• Mechanisms of Attack – Basic, Mechanisms of Attack – Acidic, Addition of H₂O (hydrate formation), Equilibrium
• HCN Addition (Basic mechanism), Cyanide Reduction or Hydrolysis
• Reactions of Carbonyl Compounds with Grignard Reagents
• Wittig Reaction, Wittig Mechanism
• Wittig Reactions, Retrosynthetic Analysis
• Nitrogen Nucleophiles, Synthesis of Imines
• Synthesis of Enamines
• Imine Reductions
• Addition of Alcohols
• Acetal/Ketal Protection Chemistry
• Conjugate Additions

This section contains one of the most fascinating discoveries that changed the synthesis of drugs in the pharmaceutical industry forever. For the first time in the history of mankind, organic chemists were able to control the outcome of reactions involving the alpha-carbon: the carbon atom next to a carbonyl group. Here, you will be amazed at how scientists were able to slow down the rapid movement of molecules to generate a kinetic controlled enolate vs a thermodynamic enolate and come up with a totally different but predictable and desired product. You will learn of important name reactions, novel prize laureates, reaction mechanisms, and total synthesis! 

• 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 

This section will dazzle you when you learn the concepts of electrophilic aromatic substitution and nucleophilic aromatic substitution. You will discover about electron donating and electron withdrawing groups and how you can use that knowledge to carry out total synthesis and retrosynthetic analysis of aromatic compounds. You will master which reagents you will need to propose reactions and you will learn many more mechanisms and name reactions that belong to these types of syntheses.

• 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

Moving along, you will be exposed to synthesis of amines and heterocyclic compounds. You will be able to name advanced compounds containing nitrogen, oxygen, and sulfur atoms attached. By the end of the chapter, you will be able to understand the reactivity of several important heterocycles and the reactions that they can produce.  

• Amines and Heterocyclic Compounds, Oxygen and Sulfur-Containing Saturated Heterocycles
• pKa Values, Amines are Nucleophiles
• The Resonance Contributors of Pyrrole, Electrophilic Aromatic Substitution Reactions
• Why Substitution at the 2-Position? Relative Reactivities
• Substitution Occurs at the 3-Position, Nucleophilic Substitution Occurs at the 2- and 4-Positions
• Nucleophilic Aromatic Substitution Reactions, Forming Diazonium Ions
• Reactions of the Side Chain

This section is the beginning of biomolecules. You will be able to master concepts, reactions, and naming of natural carbohydrates in the form of monosaccharides, disaccharides, and polysaccharides. This section will help you get started at understanding biochemistry and preparing you for it! 

• Carbohydrates, Stereochemistry
• Fischer Projection Protocols, Structures – From 3D to Fischer Projections
• Natural Carbohydrates
• Memorizing aldose sugars with 3-6 carbons
• Important Aldoses 3-5 carbons, Important Aldoses 6 carbons
• Acetal and Ketal Formation
• Acetal Formation Mechanism
• Haworth Projections
• From Fischer Projections to Chair Conformation
• Anomeric Excess
• Reactions of Monosaccharides – Part 1
• Reactions of Monosaccharides – Part 2
• Disaccharides, More Disaccharides
• Polysaccharides, Glycogen

With this section you will fulfill anything you need to know about undergraduate organic chemistry. Here you will learn about the blueprint of life, the synthesis, and reactions of amino acids. You will find out that they are the simplest monomeric unit capable of producing peptides. This knowledge will give you a springboard into biochemical syntheses.

• Amino Acids ‘R” Groups, Common Amino Acids
• Stereochemistry, Zwitterions, and Properties
• Table of pKa Values of Amino Acids, and Isoelectric Point (pI)
• Amino Acids – Synthesis
• Amino Acids – Reactions