Organic Chemistry I (OCHEM 201) SN1 SN2 E1 E2 Reaction Map Practice Problems
University of California, Berkeley
Organic Chemistry I (OCHEM 201) | Practice Problems

Overview
A decision-map practice sheet for substitution and elimination reactions covering substrate class, nucleophile/base strength, solvent, temperature, and stereochemistry.

Key topics
•substrate ranking for methyl, primary, secondary, tertiary
•strong nucleophile vs strong bulky base decisions
•polar protic vs polar aprotic solvents
•carbocation rearrangements and racemization
•Zaitsev vs Hofmann elimination products

Suggested study tasks
•classify 20 reaction conditions as SN1/SN2/E1/E2
•predict major products for 12 substrates
•explain stereochemical outcomes in 8 prompts
•draw a one-page decision tree
•redo missed questions by condition type

Common pitfalls
•using SN2 on tertiary centers
•ignoring bulky bases
•forgetting rearrangements in carbocation pathways
•mixing solvent effects
•predicting substitution when heat favors elimination