1. PHR 301: MEDICINAL CHEMISTRY 1 Lecture 2

2. Medicinal Chemistry and Organic Chemistry Medicinal Chemistry “Medicinal Chemistry is a discipline with a traditional focus on organic synthetic chemistry with the broad goals of drug discovery and optimization.” https://sop.washington.edu/department-of-medicinal-chemistry/ Organic Chemistry Study of carbon compounds Not a body of knowledge or facts to be memorized Relatively few general principles

3. Why Study Organic Chemistry? Organic chemistry is fun Want to be the coolest nerd in college? The go-to guy/gal for everyone’s everyday chemistry questions A little bit of organic chemistry goes a long way Should you fry your paratha with butter, margarine, or olive oil to stay healthy? Much of biochemistry (chemistry of life) involves organic chemistry Carbon (18.5%), oxygen (65%), hydrogen (9.5%), and nitrogen (3%) make up more than 96% of your body mass They are also the buddies carbon likes to hang out with Tremendous predictive power Without breaking your back, could teach you intellectual discipline and analytical tools that you can apply to other disciplines A wide range of applications

4. Food for Thought Where did the carbon atom come from? Why was carbon chosen over silicon as the building block of life?

5. Organic Chemistry Review: Key Concepts BB: Chapter 2, CG: Chapter 1 Periodic Table: http://www.ptable.com Octet Rule Electronegative and electropositive elements Chemical bonds: Ionic Co-valent Non-polar Polar Nucleophilic and electrophilic atoms Double and triple bonds Lewis structures Activation energy and catalysis (CG Chapter 4) Enzymes are the finest catalysts ever! Acid-Base Reactions (CG Chapter 4) Oxidation and Reduction (CG Chapter 2) IUPAC nomenclature (CG Chapter 2)

7. Organic Chemistry Review: Key Concepts BB: Chapter 2, CG: Chapter 1 Periodic Table: http://www.ptable.com Octet Rule Electronegative and electropositive elements Chemical bonds: Ionic Co-valent Non-polar Polar Nucleophilic and electrophilic atoms Double and triple bonds Lewis structures Activation energy and catalysis (CG Chapter 4) Enzymes are the finest catalysts ever! Oxidation and Reduction (CG Chapter 2) IUPAC nomenclature (CG Chapter 2)

8. Let’s fill in the blanks: semester-long group activity

9. Major Functional Groups (Organic Chemistry. Carey. 9 th Edition) ExampleCharacteristic Reaction TypeExample and Use Hydrocarbons AlkanesFree-radical substitution AlkenesElectrophilic addition to double bond Unsymmetrical alkenesElectrophilic addition to double bond, free-radical addition AlkynesElectrophilic addition to triple bond DienesElectrophilic addition to double bonds (1,2 and 1,4 addition) ArenesElectrophilic aromatic substitution Hydrocarbon derivatives Alkyl halidesNucleophilic substitution, elimination Alenyl halidesElectrophilic addition to double bond, elimination Aryl halidesElectrophilic/nucleophilic aromatic substitution Oxygen-containing organic compounds AlcoholsDehydration, conversion to alkyl halides, esterification PhenolsElectrophilic aromatic substitution EthersCleavage by hydrogen halides EpoxidesNucleophilic ring opening AldehydesNucleophilic addition to carbonyl group KetonesNucleophilic addition to carbonyl group

10. Major Functional Groups (Organic Chemistry. Carey. 9 th Edition) ExampleCharacteristic Reaction TypeExample and Use Carboxylic acids and derivatives Carboxylic acidsIonization of carboxyl; esterification Acyl halidesNucleophilic acyl substitution Acid anhydridesNucleophilic acyl substitution EstersNucleophilic acyl substitution AmidesNucleophilic acyl substitution Nitrogen-containing organic compounds AminesNitrogen acts as a nucleophile NitrilesNucleophilic addition to carbon-nitrogen triple bond Nitro compoundsReduction of nitro group to amine Sulphur-containing organic compounds ThiolsOxidation to a sulfenic, sulfinic, or sulfonic acid or to a disulfide SulfidesAlkylation to a sulfonium salt, oxidation to a sulfoxide or sulfone