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Organic Chemistry II - Summary of Preparations - Page 1

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Organic Chemistry II - Summary of Preparations

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Organic Chemistry II - Summary of Preparations - Page 1 preview imageStudy GuideOrganic Chemistry II–Summary of Preparations1.Preparations: Aryl Halides1.Halogenation of Benzene•What happens?Benzene undergoes halogenation in the presence of a halogen (X₂) and a Lewis acid catalyst(such as AlCl₃). This leads to the substitution of a hydrogen atom on the benzene ring with ahalogen atom.•What’s used?A halogen (X₂) such as chlorine (Cl₂) or bromine (Br₂), and an AlCl₃catalyst.•Reaction:
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Organic Chemistry II - Summary of Preparations - Page 2 preview imageStudy Guide2.Sandmeyer Reaction•What happens?In the Sandmeyer reaction, an amino group (-NH₂) on a benzene ring is converted to a halogen(usually bromine or chlorine) by first diazotizing the amine group with sodium nitrite (NaNO₂)and hydrochloric acid (HCl), followed by treatment with a copper halide (CuX).•What’s used?Sodium nitrite (NaNO₂), hydrochloric acid (HCl), copper(I) halide (CuX), and the appropriatehalogen.•Reaction:(with CuBr as the catalyst for bromine substitution)2.Preparations: Ethers1.Sulfuric Acid Process•What happens?The sulfuric acid process involves the dehydration of alcohols to form ethers. Alcohol undergoesan acid-catalyzed elimination reaction with sulfuric acid (H₂SO₄), resulting in the formation ofan ether and water.
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Organic Chemistry II - Summary of Preparations - Page 3 preview imageStudy Guide•What’s used?Alcohol (R-OH) and concentrated sulfuric acid (H₂SO₄).•Reaction:2.Williamson Synthesis•What happens?The Williamson synthesis is an important method for forming ethers through an SN2 reaction. Itinvolves the reaction of an alkoxide ion (RO⁻) with a primary alkyl halide (RX), leading to theformation of an ether.•What’s used?An alkoxide ion (RO⁻), an alkyl halide (RX), and heat (Δ).•Reaction:3.Preparations: Alcohols1.Williamson Synthesis
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Organic Chemistry II - Summary of Preparations - Page 4 preview imageStudy Guide•What happens?The Williamson synthesis is used to prepare alcohols via the reaction of an alkoxide ion (RO⁻)with a primary alkyl halide (RX) in a nucleophilic substitution reaction. This leads to theformation of an ether, which can be converted into an alcohol if water is added.•What’s used?Alkoxide ion (RO⁻), alkyl halide (RX), and water (H₂O).•Reaction:2.Hydroboration-Oxidation•What happens?In the hydroboration-oxidation reaction, an alkene reacts with borane (BH₃) to form atrialkylborane intermediate, which is then oxidized using hydrogen peroxide (H₂O₂) to form analcohol.•What’s used?Borane (BH₃), hydrogen peroxide (H₂O₂).•Reaction:
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Organic Chemistry II - Summary of Preparations - Page 5 preview imageStudy Guide3.Reduction of Aldehydes and Ketones•What happens?Aldehydes and ketones can be reduced to alcohols using lithium aluminum hydride (LiAlH₄) as areducing agent.•What’s used?Lithium aluminum hydride (LiAlH₄) and water (H₂O).•Reaction:4.Reduction of Carboxylic Acids
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Organic Chemistry II - Summary of Preparations - Page 6 preview imageStudy Guide•What happens?Carboxylic acids can be reduced to alcohols using lithium aluminum hydride (LiAlH₄).•What’s used?Lithium aluminum hydride (LiAlH₄) and water (H₂O).•Reaction:5.Reduction of Esters•What happens?Esters can be reduced to alcohols using lithium aluminum hydride (LiAlH₄), producing a primaryalcohol and an alcohol derived from the ester group.•What’s used?Lithium aluminum hydride (LiAlH₄) and water (H₂O).•Reaction:
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Organic Chemistry II - Summary of Preparations - Page 7 preview imageStudy Guide6.Grignard Reagent with Aldehydes and Ketones•What happens?Grignard reagents (RMgBr) react with aldehydes or ketones to form alcohols through nucleophilicaddition. The intermediate product is then treated with acid to form the alcohol.•What’s used?Grignard reagent (RMgBr), acid (H⁺).•Reaction (Aldehyde):Key Takeaway•Williamson Synthesis:Alcohols can be synthesized by nucleophilic substitution between analkoxide and an alkyl halide.•Hydroboration-Oxidation:Alkenes undergo hydroboration followed by oxidation to formalcohols.•Reduction of Aldehydes, Ketones, Carboxylic Acids, and Esters:LiAlH₄reduces carbonylcompounds to alcohols.•Grignard Reagent:Grignard reagents add to aldehydes and ketones, forming alcohols uponacid work-up.
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Organic Chemistry II - Summary of Preparations - Page 8 preview imageStudy Guide4.Preparations: Aldehydes1.Oxidation of Primary Alcohols•What happens?Primary alcohols can be oxidized to aldehydes using an oxidizing agent like pyridiniumchlorochromate (PCC). The reaction occurs in the presence of a solvent like dichloromethane(CH₂Cl₂).•What’s used?Pyridinium chlorochromate (C₆H₅N⁺HCrO₃Cl⁻) and dichloromethane (CH₂Cl₂).•Reaction:2.Reduction of Acyl Halides•What happens?Acyl halides (R-CO-Cl) are reduced to aldehydes using lithium tri-tert-butoxyaluminum hydride(LATB-H) at low temperatures.•What’s used?Lithium tri-tert-butoxyaluminum hydride (LATB-H) and water (H₂O).
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Organic Chemistry II - Summary of Preparations - Page 9 preview imageStudy Guide•Reaction:3.Reduction of Esters•What happens?Esters can be reduced to aldehydes using diisobutylaluminum hydride (DIBAL-H) at lowtemperatures followed by hydrolysis.•What’s used?Diisobutylaluminum hydride (DIBAL-H) and water (H₂O).•Reaction:4.Reduction of Nitriles•What happens?Nitriles (R-C≡N) can be reduced to aldehydes using diisobutylaluminum hydride (DIBAL-H)followed by hydrolysis.•What’s used?Diisobutylaluminum hydride (DIBAL-H) and water (H₂O).
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Document Details

University
Texas A&M University
Course
Organic Chemistry II
Subject
Chemistry

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