Reaction types

  1. Substitution Reactions

    1. Free radical

      2.  

    2. Nucleophilic substitution at alkyl carbon

      1. The Corey-House Reaction

      2. Conversion of alcohols into alkyl halides

      3. Conversion of chloroalkanes and bromoalkanes into iodoalkanes

      4. Conversion of haloalkanes into alcohols

      5. The Williamson synthesis of ethers

      6. Reaction of acetylide ions with haloalkanes

        7. RX + -CºC- ® -CºC-R

      7. Reaction of alkyl halides with cyanide

        8. RX + CN- ® RCN

      8. Reaction of alkyl halides with ammonia and amines

      9. Alkylation

    3. Electrophilic aromatic substitution

      1. Nitration

        2. ArH + HNO3/H2SO4 ® ArNO2

      2. Sulfonation

        3. ArH + H2SO4/SO3 ® ArSO3H

      3. Halogenation

        4. ArH + X2/Fe ® ArX

      4. Friedel-Crafts alkylation

        5. ArH + RX/AlCl3 ® ArR

      5. Azo compound formation

      6. Friedel-Crafts acylation

        7. ArH + RCOCl/AlCl3 ® ArCOR

    4. Nucleophilic substitution at acyl carbon

      1. acid chlorides formation from carboxylic acids

      2. ester formation from acid chlorides

      3. amide formation from acid chlorides

      4. ketone formation from acid chlorides

      5. anhydride formation from acid chlorides

      6. Transesterification

      7. Reaction of esters with Grignard reagents

    5. Nucleophilic aromatic substitution - diazonium salts

      1. The Sandmeyer reaction

      2. The Gattermann reaction

      3. Introduction of F

      4. Introduction of I

      5. Introduction of CN

      6. Introduction of OH

      7. Introduction of H

  2. Addition Reactions

    1. Ionic electrophilic addition reactions

      1. Hydrogenation of alkenes and alkynes

      2. Diels-Alder reaction - a 1,4 concerted (pericyclic) addition

      3. Markovnikov addition of HX to alkenes and alkynes

      4. Addition of halogen to alkenes and alkynes

      5. Hydration of alkenes

      6. Halohydrin formation

      7. Oxymercuration - demercuration of alkenes

      8. Hydroboration of alkenes

      9. Hydroxylation of alkenes

      10. Ozonolysis

      11. Hydration of alkynes - keto-enol tautomerism

      12. 1,2 and 1,4 addition to conjugated dienes

    2. Free radical electrophilic addition to alkenes

      1. Polymerization

      2. Addition of HBr to alkenes in the presence of peroxides

       

    3. Nucleophilic addition to aldehydes and ketones (and carbon dioxide)

      1. Addition of Grignard reagents

        2.  

      2. Addition of cyanide

      3. Addition of ammonia derivatives - imine formation

      4. Addition of alcohols to aldehydes - acetal formation

      5. The Wittig reaction

      6. The Cannizzaro reaction

      7. Reductive amination of aldehydes and ketones

      8. Aldol condensation

      9. Glucosamine formation

      10. Osazone formation

      11. Glucoside formation

  3. Elimination reactions

    1. Dehydrohalogenation of haloalkanes

    2. Dehydration of alcohols

    3. Dehalogenation of vicinal dihalides

    4. Dehydrohalogenation of vicinal dihalides

     

  4. Substitution, elimination, addition

  5. Rearrangements

    1. Carbocation rearrangements

    2. Keto-enol tautomerism

  6. Acid-base reactions

    7. Many of the above reactions include "acid - base" reactions. Here are a few more:

    1. Acidity of hydrogens bonded to sp hybridized carbons.

    2. Acidity of alcohols

      3. ROH + M ® RO- + M+ + 0.5H2

    3. Acidity of carboxylic acids

    4. Acidity of phenols

    5. Basic character of amines

    6. Acidity of a -hydrogens of aldehydes and ketones

    7. Acidity of aminoacids

  7. Oxidations

    1. of primary alcohols and aldehydes

    2. of secondary alcohols

    3. of arenes

    4. Oxidation of aldehydes

    5. Oxidation of methyl ketones via the haloform reaction - enolate formation and acyl substitution

  8. Other reactions

    1. Hydrolysis of nitriles

      2. RCN + H3O+ ® RCO2H

    2. Lithium aluminum hydride reductions

    3. Hell-Volhard-Zelinski reaction - a mixture of acyl substitution and carbanion chemistry

    4. Rosemund reduction of acid chlorides

    5. Lithium aluminum hydride or sodium borohydride reduction of aldehydes and ketones

    6. Clemmensen and Wolff-Kishner reductions of aldehydes and ketones

    7. Hofmann degradation of amides

    8. Reduction of esters

    9. Reduction of the nitro group

Home | Faculté Saint-Jean | University of Alberta | Chemistry Department

This page is maintained by Dr. Ed Blackburn (Ed.Blackburn@UAlberta.CA), course instructor.

Updated August 23, 2002