CH204 - Test 1 Rxns

HX addition to Alkenes

1) resonance stabilized

2) more substituted

Hydration: Addition of H₂O → OH/H

1) resonance

2) more substituted carbon

Alcohol Addition → OR/H

1. resonance stabilization

2. more substituted carbon

Intramolecular Reactions

Electrophilic Addition via Three-Membered Rings

• this is stereospecific

Cyclopropanation

Cyclopropanation: Dichlorocarbene

• stereospecific

Simmons-Smith Reaction

Epoxide synthesis: peracids

• also goes for the more substituted carbons

Good Nucleophile Epoxide Opening

• adds to the less substituted side

• invert stereochemistry

Hydrides and Organometallics as Nucleophiles

Hydride Addition

Opening of Epoxide w/ Grignard Reagents

involves nucleophilic attack by Grignard reagent, leading to ring opening and formation of an alcohol.

Opening of Epoxide w/ Lithium Reagents

Acid Catalyzed Ring Opening

Addition of X₂ to Alkenes

Addition of X/OH

Addition of X/OR

Oxymercuration/Reduction: Addition of OH/H