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    Organic Chem Reactions

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    Teo Jia Ming Nickolas
    The document summarizes common organic chemistry reactions for various functional groups including alkanes, alkenes, alcohols, aromatic compounds, and others. It describes characteristic reactions such as substitution, elimination, oxidation, reduction, hydration, and more. It also outlines methods of synthesizing compounds from precursor functional groups through reactions like hydrogenation, dehydration, halogenation, and Friedel-Crafts alkylation.

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    Organic Chem Reactions

    Uploaded by

    Teo Jia Ming Nickolas
    1K views7 pages
    The document summarizes common organic chemistry reactions for various functional groups including alkanes, alkenes, alcohols, aromatic compounds, and others. It describes characteristic reactions such as substitution, elimination, oxidation, reduction, hydration, and more. It also outlines methods of synthesizing compounds from precursor functional groups through reactions like hydrogenation, dehydration, halogenation, and Friedel-Crafts alkylation.

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    H2 Chemistry Organic Chem Reactions

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    The document summarizes common organic chemistry reactions for various functional groups including alkanes, alkenes, alcohols, aromatic compounds, and others. It describes characteristic reactions such as substitution, elimination, oxidation, reduction, hydration, and more. It also outlines methods of synthesizing compounds from precursor functional groups through reactions like hydrogenation, dehydration, halogenation, and Friedel-Crafts alkylation.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
    1K views7 pages

    Organic Chem Reactions

    Uploaded by

    Teo Jia Ming Nickolas
    The document summarizes common organic chemistry reactions for various functional groups including alkanes, alkenes, alcohols, aromatic compounds, and others. It describes characteristic reactions such as substitution, elimination, oxidation, reduction, hydration, and more. It also outlines methods of synthesizing compounds from precursor functional groups through reactions like hydrogenation, dehydration, halogenation, and Friedel-Crafts alkylation.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as DOCX, PDF, TXT or read online from Scribd
    Download as docx, pdf, or txt
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    The document discusses organic chemistry reactions of various functional groups including alkanes, alkenes, benzene and their derivatives.

    Common reactions of alkanes include combustion, free radical substitution, hydrogenation and decarboxylation.

    Common reactions of alkenes include addition reactions with bromine, hydrogen bromide or hydrogen, hydration, oxidation and hydrogenation.

    Organic Chem Reactions

    1. Alkanes
    a. Reactions Combustion Free-radical substitution o Steps Initiation Propagation Termination o Conditions Cl2(g)/Br2(l), UV light b. Formation Hydrogenation of Alkenes o H2(g) with Nickel catalyst, at ~150oC, ~5atm o H2(g) with Pt or Pd catalyst, at room temperature Decarboxylation of sodium salt of carboxylic acid o Heating with sodalime

    2. Alkenes
    a. Reactions Addition of bromine o Br2(l) / Br2 dissolved in CCl4, room temperature Addition of bromine water o Bromine water at room temperature Addition of HBr o HBr(g)/ HBr dissolved in CCl4, room temperature Direct hydration o Steam, H3PO4 catalyst, 300oC, 65 atm Indirect hydration o Cold concentrated H2SO4, followed by heating in the presence of water Addition of Hydrogen o H2(g) with Nickel catalyst, at ~150oC, ~5atm o H2(g) with Pt or Pd catalyst, at room temperature Oxidation o Partial bond cleavage Cold alkali/ cold, dilute acidified KMnO4 o Total bond cleavage Hot, acidified KMnO4 Combustion b. Formation Dehydration of Alcohols o Excess, concentrated H2SO4, 180oC o Al2O3, 400oC Dehydrohalogenation of halogenoalkane Done by Nickolas Teo Jia Ming, CG 12/11

    Alcoholic KOH, relfux

    3. Benzene
    a. Reactions Nitration o Concentrated HNO3, concentrated H2SO4, reflux at less than 60oC Halogenation o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature Friedel-Crafts Alkylation o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature Friedel-Crafts Acylation o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature

    4. Alkylbenzene
    a. Reactions (side-chain) Halogenation o Cl2(g)/Br2(l), UV light Oxidation o Alkaline/ acidified KMnO4, reflux o Entire side chain is oxidized into CO2H b. Formation Friedel-Crafts Alkylation o Anhydrous AlCl3 / FeCl3/ Fe power, at room temperature

    5. Alcohols
    a. Reactions Esterification o Concentrated H2SO4, reflux Acylation Halogenation (hydrogen halide) o NaCl(s), concentrated H2SO4, reflux o HX, reflux Halogenation (phosphorus halide) o Cold PCl5 o Red P and Br2, reflux o Red P and I2, reflux Halogenation (Sulfur dichloride oxide) o SOCl2, dissolved in pyridine Dehydration o Excess, concentrated H2SO4, 180oC o Al2O3, 400oC Formation of alkyl hydrogensulfate o Concentrated H2SO4, reflux at 80oC Combustion Oxidation o For aldehyde Acidified K2Cr2O7, heat to distill o For carboxylic acid/ ketone Done by Nickolas Teo Jia Ming, CG 12/11

    Acidified K2Cr2O7/ KMnO4 , reflux

    b. Formation Alkaline hydrolysis of halogenoalkane o Aqueous KOH, reflux Direct hydration of alkenes o Steam, H3PO4 catalyst, 300oC, 65 atm Indirect hydration of alkenes o Cold concentrated H2SO4, followed by heating in the presence of water Reduction of carbonyl compounds o H2(g) with Ni catalyst at 140oC o LiAlH4, dissolved in dry ether at room temperature c. Test Tri-iodomethane/ Iodoform test o Alkaline I2(aq), heat o Solid I2, NaOH(aq), heat o NaOI(l), heat

    6. Phenol
    a. Reactions Esterification o Acid chloride and NaOH(aq) Halogenation o Br2 dissolved in CCl4 o Chlorine/ Bromine water at room temperature Nitration o Dilute HNO3, room temperature b. Test Neutral Iron(III) chloride solution at room temperature o Violet coloration Bromine water at room temperature o Decolourisation and white precipitate

    7. Aliphatic carbonyl compounds


    a. Reactions Oxidation of aldehydes o Acidified K2Cr2O7/ KMnO4 , heat o Alkaline KMnO4 , heat o Tollens Reagent, heat Ammoniacal silver(I) nitrate o Fehlings Solution, heat Alkaline copper(II) tartrate Reduction o H2(g) with Ni catalyst at 140oC o LiAlH4, dissolved in dry ether at room temperature Addition of HCN o Slightly alkaline HCN (aq) at 10-20oC Done by Nickolas Teo Jia Ming, CG 12/11

    o HCN (aq), small amount of KCN, 10-20oC Condensation reaction with Bradys Reagent o Bradys Reagent, room temperature. b. Test Tri-iodomethane test o Alkaline I2(aq), heat o Solid I2, NaOH(aq), heat o NaOI(l), heat c. Formation Oxidation of alcohols o Acidified K2Cr2O7/ KMnO4 , heat (to distill for aldehyde)

    8. Aromatic carbonyl compounds


    a. Reactions Oxidation of aldehydes o Acidified KMnO4 , heat o Alkaline KMnO4 , heat o Tollens Reagent, heat Ammoniacal silver(I) nitrate o NOT Fehlings solution Reduction o LiAlH4, dissolved in dry ether at room temperature Condensation reaction with Bradys Reagent o Bradys Reagent, room temperature. Electrophilic substitution of benzene ring o Fuming HNO, concentrated H2SO4, reflux at 40oC o Cl2 , anhydrous FeCl3, at room temperature b. Test Tri-iodomethane test o Alkaline I2(aq), heat o Solid I2, NaOH(aq), heat o NaOI(l), heat c. Formation For benzaldehyde o Excess Cl2 gas and UV light, followed by reflux with NaOH (aq) For phenylethanone o CH3COCl with anhydrous AlCl3 catalyst, 40oC

    9. Carboxylic acid
    a. Reactions Metal, metal carbonate, alkali o Room temperature Formation of acyl chloride by a halogen atom o PCl5(s), cold o PCl3(l), cold o SOCl2, dissolved in pyridine Esterification Done by Nickolas Teo Jia Ming, CG 12/11

    o Concentrated H2SO4, reflux Reductions o LiAlH4, dry ether, room temperature b. Formation Oxidation of primary alcohol o Acidified K2Cr2O7/ KMnO4 , reflux Oxidation of aldehydes o Acidified K2Cr2O7/ KMnO4 , reflux Oxidation of methyl benzene o Acidified KMnO4 , heat o Alkaline KMnO4 , heat Acid hydrolysis of nitriles o Dilute HCl, reflux Alkali hydrolysis of nitriles o Dilute NaOH, reflux, followed by acidify

    10.Carboxylic acid derivatives


    a. Reactions Hydrolysis o Ester Dilute H2SO4, reflux o Acyl chloride Water, room temperature o Amide Dilute HCl, reflux React with alcohol/ phenol o Acyl chloride Room temperature Reaction with NH3 o Ester Concentrated alcoholic NH3 o Acyl chloride Room temperature Reduction o Ester LiAlH4, dissolved in dry ether at room temperature o Acyl chloride LiAlH4, dissolved in dry ether at room temperature o Amide LiAlH4, dissolved in dry ether at room temperature b. Formation Acyl chloride o Formation of acyl chloride by a halogen atom Ester o Esterification Done by Nickolas Teo Jia Ming, CG 12/11

    Amide o Acyl chloride, NH3/ RNH2/ R2NH, cold

    11. Amine
    a. Reactions Alkylation of amine o RX dissolved in ethanol in a sealed tube; Heat Acylation of amine o Acyl chloride; Cold b. Formation Reduction of nitriles o LiAlH4, dry ether, room temperature o H2(g) with Ni catalyst at 140oC o Na and ethanol Reduction of amides o LiAlH4, dry ether, room temperature o H2(g) with Ni catalyst at 140oC o Na and ethanol

    12. Phenylamine
    a. Reactions Alkylation of amine o RX dissolved in ethanol in a sealed tube; Heat Acylation of amine o Acyl chloride; Cold Halogenation o Br2 dissolved in CCl4 o Chlorine/ Bromine water at room temperature b. Formation Reduction of nitrobenzene o Sn, concentrated HCl, reflux followed by addition of NaOH (aq)

    13. Halogenoalkane
    a. Reactions Nucleophilic substitution o Alkaline hydrolysis NaOH (aq); Reflux KOH (aq); Reflux o Formation of Nitrile Alcoholic KCN; Reflux o Formation of ether Na in excess alcohol; Reflux o Formation of ester Silver(I) salt of carboxylic acid in alcohol; Reflux o Formation of amine Excess concentrated NH3 in alcohol; Reflux Elimination o Dehalogenation of halogenoalkane Done by Nickolas Teo Jia Ming, CG 12/11

    Alcoholic KOH; Reflux Alcoholic CH3O-Na+; Reflux

    b. Formation Free radical substitution of alkane Halogenation of alcohols Addition of halogen to alkene

    Done by Nickolas Teo Jia Ming, CG 12/11

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