OrgoChem I

Alkenes

Addition reactions and how reagents map to outcomes

Summary

Learn reagent to product patterns and stereochemistry of addition. Full reference is on the external link.

What you need to know:

This topic covers alkenes. Focus on mastering the key concepts in the "Must know checklist" below. Follow the study steps systematically, and use practice problems to reinforce your understanding. The external reference provides comprehensive coverage of all concepts.

Video Tutorial

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Alkene Reactions Made Simple - Mechanisms, Markovnikov's Rule, Lots of Practice

Click to watch on YouTube →

Must know checklist

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MarkovnikovH adds to less substituted C, X adds to more substituted C (HX, acid-catalyzed hydration); anti-Markovnikov: opposite (hydroboration-oxidation)
Alkene Reactions Made Simple - Mechanisms, Markovnikov's Rule, Lots of Practice→
Key reactionsHX (Markovnikov), X2 (anti addition), halohydrin (X2/H2O), hydration (H+/H2O), oxymercuration (Markovnikov, no rearrangement), hydroboration (anti-Markovnikov, syn addition)
Markovnikov's Rule vs Anti-Markovnikov in Alkene Addition Reactions→
Stereochemistrysyn addition (H2/Pd, hydroboration) = both add from same face; anti addition (X2, halohydrin) = add from opposite faces
Syn vs Anti Addition Stereochemistry in Alkene Reactions→
Carbocation rearrangementshydride shift (H-) or methyl shift (CH3-) to form more stable carbocation (3° > 2° > 1°)
Carbocation Rearrangements - Hydride and Methyl Shifts Explained→
Ozonolysiscleaves C=C to carbonyls; terminal alkene → aldehyde + HCHO; internal alkene → two carbonyls; identify original alkene from products
Ozonolysis - Oxidative Cleavage of Alkenes→

Common mistakes

Assuming Markovnikov always applies

Forgetting syn vs anti addition outcomes

Not checking rearrangements in carbocation pathways