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Organic Chemistry - Reaction Mechanisms - Addition, Elimination, Substitution, & Rearrangement

Organic Chemistry Reactions Study Guide

1. Reaction Types

  • Addition Reactions: Involves the addition of atoms or groups to a double or triple bond.

    • Example: Hydrogenation of alkenes.

  • Elimination Reactions: Atoms or groups are removed, often forming a double or triple bond.

    • Example: Dehydration of alcohols.

  • Substitution Reactions: An atom or group in a molecule is replaced by another atom or group.

    • Example: Halogenation of alkanes.

  • Redox Reactions: Involves the transfer of electrons, leading to changes in oxidation states.

    • Example: Oxidation of alcohols to ketones or aldehydes.

2. Key Reagents and Conditions

  • Nucleophiles: Chemicals that donate an electron pair, participate in nucleophilic substitution and addition reactions.

  • Electrophiles: Chemicals that accept electrons; often involved in addition reactions.

  • Catalysts: Substances that increase the rate of reaction without being consumed.

3. Mechanisms

  • Markovnikov's Rule: In addition reactions, the more stable carbocation forms preferentially, leading to the more substituted product.

  • Anti-Markovnikov Addition: Occurs with the presence of certain reagents such as peroxides in the addition of HBr to alkenes, leading to less substituted products.

  • SN1 and SN2 Mechanisms:

    • SN1: Two-step reaction, involves formation of a carbocation.

    • SN2: One-step mechanism, involves direct interaction of nucleophile and electrophile.

4. Common Reaction Examples

  • Esterification: Formation of esters from carboxylic acids and alcohols.

  • Grignard Reactions: Reactions involving Grignard reagents to form alcohols.

  • Aldol Condensation: Forms β-hydroxy aldehydes or ketones via nucleophilic addition of aldehyde with alpha-hydrogen.

5. Practice Problems

  • Predict the products of given reaction mechanisms.

  • Identify reaction types from reaction schemes.

  • Memorize key reagents for each reaction type.

6. Tips for Studying

  • Use flashcards for key terms and reagents.

  • Practice with reaction mechanisms to understand the steps involved.

  • Solve past exam questions to familiarize with common organic reactions.