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  • Chapter

    • Alkene Reactions

      • 1.  HX Addition*

        • a.  Addition of HX

        • b.  Addition of HX with peroxide

      • 2.  Hydration*

        • a.  Acid catalyzed

        • b.  Oxymercuration-demercuration in water

        • b.  Oxymercuration-demercuration in alcohol

        • c.  Hydroboration-oxidation

      • 3.  Hydrogenation

        • a.  Metal Catalyzed

      • 4.  Halogenation    cis alkene gives racemic, trans alkene gives meso*

        • a.  Addition of X2

        • b.  Addition of X and OH

      • 5.  Synthesis of Alkenes

        • a.  Elimination*

          • i.  E1        First order, reaction only depends on concentration of R-X
                         rearrangement common
                         often weak base
                         ionizing solvent to promote the X- to leave
                         3° and 2° are best

          • ii. E2        Second order
                         coplanar transition state required,
                         alkane orientation is often anti
                         cycloalkanes must have the H and the X trans-diaxial
                         strong base required
                         1° and 2° are best

      • 6.  Dehalogenation of vicinal dibromides

      • 7.  Dehydration of alcohols

  • Chapter

    • Alcohol Synthesis

      • I. From Alkanes

        • 1. Hydration REVIEW*

          • a. Acid catalyzed

          • b. Oxymercuration-demurcuration

          • c. Hydrobromination-oxidation

        • 2. Hydroxylation: forms vicinal diols (glycols)*

          • a. Syn hydroxylation

          • b. Anti hydroxylation

      • II. From alkyl halides: Nucleophilic Substitution

        • 1. Nucleophilic Substitution*

          • a. Sn1

          • b. Sn2

      • III. From carbonyl compounds: Nucleophilic Addition to the carbonyl group

        • 1. Addition of a Grignard or organolithium reagent*

          • a. Addition to formaldehyde gives 1° alcohol

          • b. Addition to an aldehyde gives 2° alcohol

          • c. Addition to a ketone gives 3° alcohol

          • d. Addition to an acid halide or and ester gives 3° alcohol

          • e. Addition to ethylene oxide gives a primary alcohol and 2 carbon atoms added

        • 2.  Reduction of carbonyl compounds*

          • a.  Catalytic hydrogenation of aldehydes and ketones

          • b.  Use of hydride reagents*

            • 1.  Reduction of and aldehyde gives 1° alcohol

            • 2.  Reduction of a ketone gives 2° alcohol

            • 3.  Reduction of an acid or ester gives 1° alcohol

  • Chapter 11

    • Reactions of Alcohols

      • 1. Oxidation-reduction reactions*

        • a.  Oxidation of secondary alcohols to ketones

        • b.  Oxidation of primary alcohols to carboxylic acids

        • c.  Oxidation of primary alcohols to aldehydes

        • d.  Reduction of alcohols to alkanes

      • 2.  Cleavage of alcohol hydroxyl group*

        • a.  Conversion of alcholols to alkyl halides

        • b.  Dehydration of alchols to form alkenes

        • c.  Industrial dehydration of alcohols to form ethers

        • d.  Unimolecular dehydration

      • 3.  Cleavage of the hydroxyl proton*

        • a.  Tosylation

        • b.  Acylation to form esters

        • c.  Deprotonation to form an alkoxide

        • d.  Williamson ether synthesis

      • 4.  Diols*

        • a.  Pinacol rearrangement

        • b.  Periodic acid cleavage of glycols

  • Chapter 14

    • Synthesis of Ethers

      • 1.  The Williamson ether synthesis

      • 2.  Addition of an alcohol across a double bond: alkoxymercuration-demercuration

      • 3.  Bimolecular dehydration of alcohols: industrial synthesis

    • Reactions of Ethers

      • 1.  Cleavage by HBr and HI

      • 2.  Autoxidation

    • Epoxide Syntheses

      • 1.  Peroxyacid epoxidation

      • 2.  Base-promoted cylclization of halohydrins

    • Reactions of Epoxides

      • 1.  Acid-catalyzed opening*

        • a.  In water

        • b.  In alcohols

        • c.  Using haydrohalic acids

      • 2.  Base-catalyzed opening*

        • a.  With alkoxides

        • b.  With organometallics

  • Chapter 15

    • Conjugated Systems

      • 1.  1,2- and 1,4-addition to a conjugated diene

      • 2.  The Diels-Alder Reaction*

        • a.  Concerted Mechanism

        • b.  Endo Rule

        • c.  1,4 Addition

        • d.  1,2 Addition

        • e.  [4+2] Addition

        • f.   [2+2] Addition

  • Chapter 17

    • Reactions of Aromatic Compounds

      • 1.  Electrophilic aromatic substitution*

        • a.  Halogenation

        • b.  Nitration

        • c.  Sulfonation

        • d.  Friedel-Crafts alkylation

        • e.  Friedel-Crafts acylation

        • f.  Gatterman-Koch synthesis

        • g.  Substituent effects

      • 2.  Nucleophilic aromatic substitution

      • 3.  Addition Reactions*

        • a.  Chlorination

        • b.  Catalytic hydrogenation

        • c.  Birch Reduction

      • 4.  Side-chain reactions*

        • a.  The Clemmensen reduction (converts acylbenzenes to alkylbenzenes)

        • b.  Permanganate oxidation

        • c.  Side-chain halogenation

        • d.  Nucleophilic substitution at the benzylic position

      • 5.  Oxidation of phenols to quinones

  • Chapter 18

    • Synthesis of Ketones and Aldehydes

      • 1.  Oxidation of Alcohols*

        • a.  Oxidation of 2° alcohols to ketones

        • b.  Oxidation of 1° alcohols to aldehydes

      • 2.  Ozonolysis of Alkenes

      • 3.  Friedel-Crafts acylation

      • 4.  Gatterman-Koch synthesis

      • 5.  Hydration of Alkynes*

        • a.  Catalyzed by acid and mercuric salts (Markovnikov)

        • b.  Hydroboration-oxidation (anti-Markovnikov)

      • 6.  Alkylation of 1,3-dithianes

      • 7.  Synthesis of ketones using organolithium reagents with carboxylic acids

      • 8.  Synthesis of ketones from nitriles

      • 9.  Aldehyde synthesis by reduction of acid chlorides

      • 10.  Ketone synthesis from acid chlorides

    • Reactions of Ketones and Aldehydes

      • 1.  Addition of organometallic reagents

      • 2.  Reduction

      • 3.  The Wittig reaction

      • 4.  Hydration

      • 5.  Formation of cyanohydrins

      • 6.  Formation of imines (condensation)

      • 7.  Formation of oximes and hydrazones (condensation)

      • 8.  Formation of acetals

      • 9.  Oxidation of aldehydes

      • 10.  Deoxygenation reactions*

        • a.  Clemmensen reduction

        • b.  Wolff-Kishner reduction

    • General Notes

      • 1.  Nucleophilic Addition

      • 2.  Acid-catalyzed

      • 3.  Reactivity

  • Chapter 19

    • Reactions of Amines

      • 1.  Reaction as a proton base

      • 2.  Alkylation

      • 3.  Acylation to form amides

      • 4.  Reaction with sulfonyl chlorides to give sulfonamides

      • 5.  Diazotization*

        • a.  Reactions of diazonium salts*

          • i.  Hydrolysis

          • ii.  The Sandermeyer reaction

          • iii.  Replacement by flouride or iodide

          • iv.  Reduction to hydrogen

          • v.  Diazo coupling

    • Synthesis of Amines

      • 1.  Reductive amination ADDS 1 R Group*

        • a.  Primary amines

        • b.  Secondary amines

        • c.  Tertiary amines

      • 2.  Acylation-reduction of amines ADDS 1 Alkyl group

      • 3.  Alkylation of ammonia

      • 4.  Reduction of azides ADDS NH3

      • 5.  Reduction of nitriles ADDS CH2NH2

      • 6.  Reduction of nitro compounds

      • Example of multistep synthesis

      • Summary of Diazotization

  • Chapter 20

    • Synthesis of Carboxylic Acids

      • 1.  Oxidation of primary alcohols and aldehydes

      • 2.  Oxidation cleavage of alkenes and alkynes

      • 3.  Oxidation of alkylbenzenes

      • 4.  Carboxylation of Grignard reagents ADDS 1 R group

      • 5.  Formation and hydrolysis of nitriles ADDS 1 C

    • Reactions of Carboxylic Acids

      • General Types of Reactions

      • 1.  Salt formation

      • 2.  Conversion to acid chlorides

      • 3.  Conversion to esters, Fischer esterification


      • 4.  Conversion to amides

      • 5.  Conversion to anhydrides

      • 6.  Reduction to primary alcohols

      • 7.  Reduction to aldehydes

      • 8.  Alkylation to form ketones

  • Chapter 22

    • Enolate Additions and condensations

      • 1.  a Halogenation*

        • a.  The iodoform (or haloform) reaction

        • b.  The Hell-Volhard-Zelinsky ) HVZ reaction

      • 2.  Alkylation of lithium enolates

      • 3.  Alkylation of enamines

      • 4.  The aldol condensation and subsequent dehydration

      • 5.  The Claisen ester condensation, cyclizations are the Dieckmann condensation

      • 6.  The malonic ester synthesis

      • 7.  The acetoacetic ester synthesis

      • 8.  The Michael addition (conjugate addition)*

        • a.  The Robinson annulation