Organic Chemistry 1 (Chem 12A)

Organic Chemistry I covers the structure and reactions of acids and bases, hydrocarbons (alkanes, alkenes, alkynes), alkyl halides, and alcohols. Nomenclature of organic compounds, stereochemistry, and reaction mechanisms will be discussed.

Course Content, Objectives, Lecture Slides, Lecture Videos, Quiz Practice Problems, Practice Problem Solutions

pKa table (more extensive than pKa table in textbook)

Quiz Practice Problems – doing these practice problems and spreading them out over time are really good for active retrieval of information to improve your long term retention. Important: Try answering the questions first before you look at the solutions.

Objective 1: Represent organic molecules with chemical formulas, expanded formulas, Lewis structures, skeletal structures. Determine shape (VSEPR), bond polarity, and molecule polarity. Identify functional groups.

Objective 2: Compare 2 or more compounds and determine whether the compounds are structural isomers, the same compound, or different compounds. Calculate formal charge and determine most likely structure.

Objective 3: Draw resonance structures, use curved arrows, determine extent of delocalization. Identify major/minor contributor.

Objective 4: Intro to Reactivity 1: identify acids and bases using Lewis definition. Use curved arrows to show how base reacts with acid. Relate strength to pKa. Determine direction of equilibrium. Use pKa table to estimate pKa of acid based on structure.

Objective 5: Name alkanes chains and rings – parent and branches.

Objective 6: Draw conformational isomers of chains (staggered, eclipsed) and rings (chair – axial/equatorial, boat, cis/trans)using skeletal structures, Newman projections, wedge-dash, sawhorse. Identify most stable conformer.

Objective 7: Stereochemistry – identify chirality centers, determine configuration (R/S), identify enantiomers, diastereomers, and meso compounds.

Objective 8: Intro to Reactivity 2: identify polar bonds (δ + and δ-), nucleophiles (Lewis base, electron pair donor), electrophiles (Lewis acid, electron pair acceptor). Use curved arrows to predict product. Identify common bond breaking and making processes.

Objective 9: Apply reactivity principles to Substitution reactions: identify structural features (alpha C, LG), use curved arrows to predict product, compare SN1 vs. SN2 mechanisms.

Objective 10: Apply reactivity principles to Elimination reactions: identify structural features (alpha C, H on beta C, LG), use curved arrows to predict product, compare E1 vs. E2 mechanisms.

Objective 11: Apply reactivity principles to Substitution and Elimination reactions. Compare size and strength of nucleophile to predict major product.

Objective 12: Apply reactivity principles to Electrophilic Addition reactions 1: alkenes – identify structural features (pi bond) and electrophiles, use curved arrows to predict product.

Objective 13: Apply reactivity principles to Electrophilic Addition reactions 2: alkynes – identify structural features (pi bond) and electrophiles, use curved arrows to predict product.

Objective 14: Apply reactivity principles to radical reactions: identify radical reaction conditions, describe mechanism, use curved arrows for common radical steps to predict products.

Objective 15: Develop synthesis strategies for organic synthesis.

Objective 16: Apply organic chemistry lab skills, which include the proper use and operation of organic lab chemicals, equipment, instruments, lab techniques, and safety procedures, and critical thinking skills to experiments.

Student Learning Outcomes

By the end of the course, you should be able to apply the course objectives to:

(i) Given the name of an organic compound, relate the physical properties, chemical properties, and uses to the compound’s major functional groups and structure.

(ii) Given reactants, predict products and propose mechanisms for organic reactions.

(iii) Given an organic compound, design a synthesis.

(iv) Given IR, NMR, and mass spectra, deduce the formula and structure of organic compounds.

(v) Demonstrate proficiency in basic laboratory skills used in organic chemistry.