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Hydrohalogenation Hydrohalogenation (with Rearrangement) Halogenation Hydrobromination with Peroxide Hydration Hydration (with Rearrangement) Bromination in H 2 O Oxymercuration- Demercuration Hydroboration- Oxidation Syn-Dihydroxylation Syn-Dihydroxylation Anti-Dihydroxylation Addition of an Alcohol Bromination in Alcohol
Alkoxymercuration- Demercuration Epoxidation Catalytic Hydrogenation Pt can also be used Ozonolysis (Reducing Conditions) Ozonolysis (Oxidizing Conditions)/Oxidative Cleavage
Catalytic Hydrogenation (Catalytic Reduction) Reduction to Cis-Alkene Reduction to Trans-Alkene Hydrohalogenation with HBr (Terminal Alkyne) Hydrohalogenation with HBr (Internal Alkyne) Halogenation with Br 2 Hydration of an Internal Alkyne Hydration of a Terminal Alkyne (Markovnikov) Hydration of a Terminal Alkyne (Anti-Markovnikov)
Diene Addition to a Dienophile (Alkene) Diene Addition to a Dienophile (Alkyne) Diene Addition to a cis Dienophile Diene Addition to a trans Dienophile Diene Addition to a substituted Dienophile
Addition of a Grignard Reagent to an Aldehyde 2 ˚Alcohol Addition of a Grignard Reagent to a Ketone 3 ˚Alcohol Addition of a Grignard Reagent to an Ester 3 ˚Alcohol
Addition of a Grignard Reagent to an Acyl Chloride 3 ˚Alcohol Addition of a Grignard Reagent to CO 2 Carboxylic Acid Addition of a Grignard Reagent to an Epoxide (adds to the less subs. side) Addition of a Grignard Reagent to a Carboxylic Acid Carboxylate Addition of a Grignard Reagent to an Amide Deprotonated Amide Addition of a Grignard Reagent to a Nitrile Ketone
Friedel-Crafts Alkylation (Rearrangement Possible) Friedel-Crafts Acylation (No Rearrangement Possible) Bromination
Side-Chain Oxidation of Benzene to form Benzoic Acid Wolff-Kishner Reduction Clemmensen Reduction **can also use H 2 /Pd, C can also use H 2 /Pd, C or Sn/HCl Acetylation of Aniline using Acetic Anhydride
Reduction of an Aldehyde to a 1 ˚Alcohol Reduction of a Ketone to a 2 ˚Alcohol Reduction of a Carboxylic Acid to a 1 ˚Alcohol Reduction of an Ester to a 1 ˚Alcohol Reduction of an Ester to an Aldehyde
Chromic Acid Oxidation of a 1 o^ Alcohol to a Carboxylic Acid Chromic Acid Oxidation of a 2 o^ Alcohol to a Ketone Chromic Acid Oxidation of an Aldehyde to a Carboxylic Acid PCC or DMP Oxidation of a 1 o^ Alcohol to an Aldehyde PCC or DMP Oxidation of a 2 o^ Alcohol to a Ketone Oxidative Cleavage of a 1 , 2 Diol Swern Oxidation
Williamson Ether Synthesis via SN 2 Acid-catalyzed Cleavage of Ethers when one side is 2 ˚/ 3 ˚ (Nucleophile attacks more substituted side via SN 1 )
Acid-catalyzed Cleavage of Ethers when neither side is 2 ˚/ 3 ˚ (Nucleophile attacks less substituted side via SN 2 ) Acid-catalyzed Ring Opening of Epoxides (Nucleophile attacks more substituted side) Base-catalyzed Ring Opening of Epoxides (Nucleophile attacks less substituted side)
Nucleophilic Addition to an Aldehyde or Ketone Addition of water to an Aldehyde or Ketone forming a Hydrate Base-catalyzed addition of an Alcohol to an Aldehyde or Ketone forming a Hemi-acetal/Hemi-ketal Acid-catalyzed addition of an Alcohol to an Aldehyde or Ketone forming a Acetal/Ketal (Protecting Group, reversed by H 3 O+) Acid-catalyzed addition of Ethylene Glycol to an Aldehyde or Ketone forming a Acetal/Ketal (Protecting Group, reversed by H 3 O+) Addition of a 1 ˚ Amine to an Aldehyde or Ketone forming an Imine (Reversed by H 3 O+)
Self Aldol Condensation and Enone Formation Mixed Aldol Condensation and Enone Formation Self Claisen Condensation Mixed Claisen Condensation
Dieckmann Cyclization (Intramolecular Claisen Condensation) Acetoacetic Ester Synthesis Malonic Ester Synthesis Alpha Halogenation In Basic Conditions Alpha Halogenation in Acidic Conditions Haloform Reaction *A methyl group is required for this reaction
Halogenation What’s added: 2 Br atoms Stereoselectivity : Anti Intermediate: Bromonium ion Rearrangement: Not possible Mechanism: Hydrobromination with Peroxide What’s added: H⋅ and Br⋅ Regioselectivity: Anti-Markovnikov Intermediate: Radical Rearrangement: Not possible Mechanism:
Hydration What’s added: H+^ and OH- Regioselectivity: Markovnikov Intermediate: Carbocation Rearrangement: Possible (methyl and hydride shifts) Mechanism: Bromination in H 2 O What’s added: Br+^ and OH- Regioselectivity: Markovnikov Stereoselectivity : Anti Intermediate: Bromonium ion Rearrangement: Not possible Mechanism: Oxymercuration-Demercuration What’s added: H+^ and OH- Regioselectivity: Markovnikov Stereoselectivity : Anti Intermediate: Mercurinium ion bridge Rearrangement: Not possible
Anti-Dihydroxylation What’s added: 2 OH groups Stereoselectivity : Anti Rearrangement: Not possible In acidic conditions, the H 2 O attacks the more highly-substituted C: In basic conditions, H 2 O attacks the less highly-substituted C: Addition of an Alcohol What’s added: H+^ and OR- Regioselectivity: Markovnikov Intermediate: Carbocation Rearrangement: Possible Mechanism:
Bromination in Alcohol What’s added: Br+^ and OR- Regioselectivity: Markovnikov Stereoselectivity : Anti Intermediate: Bromonium ion Rearrangement: Not possible Mechanism: Alkoxymercuration-Demercuration What’s added: H+^ and OCH 3 - Regioselectivity: Markovnikov Stereoselectivity : Anti Intermediate: Mercurinium ion Rearrangement: Not possible Epoxidation What’s added: O Stereoselectivity : Syn Rearrangement: Not possible Know that a commonly-used peroxy acid is m - CPBA:
