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    Prep and Properties of Alkane Alkene and Alkyne

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    SEBASTIEN ANDREI BUENAFE
    The document summarizes methods for preparing alkanes, alkenes, and alkynes including: 1. Soda-lime process, Wurtz synthesis, and Grignard reaction for preparing alkanes. 2. Dehydration of alcohols, dehydrohalogenation of alkyl halides, and dehalogenation of alkyl dihalides for preparing alkenes. 3. Laboratory preparation of acetylene, dehydrohalogenation of alkyl dihalides, and dehalogenation of alkyl tetrahalides for preparing alkynes. It also outlines properties such as combustion, Baeyer's test for unsaturation, substitution reactions, and addition reactions

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    Prep and Properties of Alkane Alkene and Alkyne

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    SEBASTIEN ANDREI BUENAFE
    49 views38 pages
    The document summarizes methods for preparing alkanes, alkenes, and alkynes including: 1. Soda-lime process, Wurtz synthesis, and Grignard reaction for preparing alkanes. 2. Dehydration of alcohols, dehydrohalogenation of alkyl halides, and dehalogenation of alkyl dihalides for preparing alkenes. 3. Laboratory preparation of acetylene, dehydrohalogenation of alkyl dihalides, and dehalogenation of alkyl tetrahalides for preparing alkynes. It also outlines properties such as combustion, Baeyer's test for unsaturation, substitution reactions, and addition reactions

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    Prep-and-Properties-of-Alkane-alkene-and-alkyne

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    The document summarizes methods for preparing alkanes, alkenes, and alkynes including: 1. Soda-lime process, Wurtz synthesis, and Grignard reaction for preparing alkanes. 2. Dehydration of alcohols, dehydrohalogenation of alkyl halides, and dehalogenation of alkyl dihalides for preparing alkenes. 3. Laboratory preparation of acetylene, dehydrohalogenation of alkyl dihalides, and dehalogenation of alkyl tetrahalides for preparing alkynes. It also outlines properties such as combustion, Baeyer's test for unsaturation, substitution reactions, and addition reactions

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    © All Rights Reserved
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    Download as pdf or txt
    49 views38 pages

    Prep and Properties of Alkane Alkene and Alkyne

    Uploaded by

    SEBASTIEN ANDREI BUENAFE
    The document summarizes methods for preparing alkanes, alkenes, and alkynes including: 1. Soda-lime process, Wurtz synthesis, and Grignard reaction for preparing alkanes. 2. Dehydration of alcohols, dehydrohalogenation of alkyl halides, and dehalogenation of alkyl dihalides for preparing alkenes. 3. Laboratory preparation of acetylene, dehydrohalogenation of alkyl dihalides, and dehalogenation of alkyl tetrahalides for preparing alkynes. It also outlines properties such as combustion, Baeyer's test for unsaturation, substitution reactions, and addition reactions

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    of 38

    Preparation of Alkanes

    1. Soda-Lime Process
    CaO
    R-COONa Na0H Na2CO3 R-H

    CaO
    CH3CH2COONa Na0H Na2CO3 CH3CH3
    Alkane
    Ethane
    2. Wurtz Synthesis
    Dry

    2 R-Cl 2 Na ether
    2 NaCl R- R
    Alkane
    R-Cl Na Dry
    ether
    R-Cl Na 2 NaCl R- R

    Dry
    ether
    2 CH3CH2-Cl 2 Na 2 NaCl CH3CH2-CH2CH3
    Butane
    Dry
    ether
    2 CH3CH2-Cl 2 Na 2 NaCl CH3CH2-CH2CH3
    Butane

    CH3CH2-Cl Na Dry
    ether
    CH3CH2-Cl Na 2 NaCl CH3CH2- CH2CH3

    Dry
    ether
    2 CH3CH2-Cl
    CH2CH3 2 Na 2 NaCl CH3CH2-CH2CH3
    3. Grignard Reaction
    Dry

    R-X Mg
    ether
    R-Mg-X H-OH Mg(OH)X R-H

    Dry

    CH3CH2-Cl Mg
    ether
    CH3CH2-MgCl H-OH Mg(OH)Cl

    CH3CH23-H
    Preparation of Alkanes
    • 1. Soda-lime process
    • 2. Wǘrtz Synthesis
    • 3. Grignard Reaction
    Preparation of Alkene
    1. Dehydration of Alcohol (Intramolecular Dehydration)

    H H H2SO4, heat
    H C C H H2O CH2=CH2
    H OH

    H2SO4, heat
    CH3CH2CH2OH H2O CH3CH = CH2
    H2SO4, heat
    CH3CHCH3 CH3CH=CH2 CH
    H2O2=CHCH3
    OH
    H2SO4, heat
    2 CH3CHCH2CH3 CH2=CHCH2CH3
    OH Minor Product
    CH3CH=CHCH3
    Major Product

    2 H2O
    2-Ethyl-3-methyl-1-butene

    OH CH2=C CH2CH3
    H2SO4, heat
    3 CH3C CH2CH3 CHCH3
    CHCH3 CH3 CH3 C=CHCH3
    CH3 CHCH3
    CH3
    3,4-dimethyl-2-pentene

    CH3 C CH2CH3
    Major Product C CH3 3 H2O
    CH3 2,3-dimethyl-2-pentene
    2. Dehydrohalogenation of alkyl halide

    H H KOH,
    ethanol

    H C C H HCl CH2=CH2
    H Cl
    KOH,
    ethanol
    CH3CH2CH2Cl HCl CH3CH = CH2
    KOH,
    ethanol
    CH3CHCH3 CH3CH=CH2 CHHCl
    2=CHCH3
    Cl
    KOH,
    ethanol
    2 CH3CHCH2CH3 CH2=CHCH2CH3
    Cl Minor Product
    CH3CH=CHCH3
    Major Product

    2 HCl
    2-Ethyl-3methyl-1-butene

    Cl KOH,
    CH2=C CH2CH3
    3 CH3C CH2CH3 ethanol
    CHCH3
    CHCH3 CH3 CH3 C=CHCH3
    CH3 CHCH3
    CH3
    3,4-dimethyl-2-pentene

    CH3 C CH2CH3
    C CH3 3 HCl
    CH3 2,3-dimethyl-2-pentene
    3. Dehalogenation of Alkyl dihalide

    H H
    H C C H Mg MgCl2 CH2=CH2
    Cl Cl

    CH3CHCH2Cl Mg MgCl2 CH3CH = CH2


    Cl
    CH3CH ̶ CHCH3 Mg MgCl2 CH3CH=CHCH3
    Cl Cl
    Preparation of Alkene
    • 1. Dehydration of Alcohol
    • 2. Dehydrohalogenation of alkyl halide
    • 3. Dehalogenation of Alkyl Dihalide
    Preparation of Alkyne
    1. Lab. Prep. of Acetylene

    CaC2 H2O Ca(OH)2 HC CH


    2. Dehydrohalogenation of alkyl dihalide
    K-OH
    H H ethanol
    H C C H 2 K-OH 2KCl 2H2O CH CH
    Cl Cl
    K-OH
    ethanol
    CH3CHCH2Cl 2 K-OH 2KCl 2H2O CH3C CH
    Cl
    3. Dehalogenation of alkyl tetrahalide

    Cl Cl
    H C C H 2 Mg 2MgCl2 CH CH
    Cl Cl

    Cl Cl
    CH3C C H 2 Mg 2MgCl2 CH3C CH
    Cl Cl
    Preparation of Alkynes
    • 1. Lab preparation of acetylene
    • 2. Dehydrohalogenation of Alkyl Dihalide
    • 3. Dehalogenation of Alkyl Tetrahalide
    Properties of Alkanes, Alkenes, and Alkynes
    1. Combustion
    Akane O2 CO2 H2O
    Akene O2 CO2 H2O

    Akyne O2 CO2 H2O


    2. Baeyers Test for Unsaturation
    Alkane KMnO4 No rxn
    H2O
    Alkene KMnO4 Diol KOH MnO2
    Brown
    ppt.
    H2O
    CH2=CH2 KMnO4 CH2 ̶ CH2 KOH MnO2
    OH OH Brown
    ppt.
    H2O
    Alkyne KMnO4 Carboxylic
    Acid KOH MnO2
    Brown
    ppt.
    H2O
    CH CH KMnO4 2 CO2 KOH MnO2
    CO2 CO2

    H2O
    CH3C CH KMnO4 CO2 CH3COOH KOH MnO2

    COOH CO2
    CH3C C ̶ CH3 KMnO4 2CH3COOH KOH MnO2

    COOH COOH

    CH3C C ̶ CH2CH3 KMnO4 CH3COOH CH3CH2COOH

    COOH COOH
    KOH MnO2
    3. Substitution Reaction (Alkane only)
    •A. Halogenation
    •B. Sulfonation
    •C. Nitration
    Halogenation
    H H
    UV
    H C H Cl ̶ Cl H C Cl HCl
    H H
    UV
    CH4 Cl2 CH3Cl HCl
    UV
    CH4 2Cl2 CH2Cl2 2 HCl
    UV
    CH4 3Cl2 CHCl3 3 HCl
    UV
    CH4 4Cl2 CCl4 4 HCl
    UV
    CH3CH3 Cl2 CH3CH2Cl HCl
    B. Sulfonation H2SO4
    H H
    H C H HOSO3H H C SO3H H2O
    H H

    CH4 H2SO4 CH3SO3H H2O


    methanesulfonic acid

    CH3CH3 H2SO4 CH3CH2SO3H H2O


    Ethanesulfonic acid
    Nitration HNO3
    H H
    H C H HONO2 H C NO2 H2O
    H H

    CH4 HNO3 CH3NO2 H2O


    Nitromethane

    CH3CH3 HNO3 CH3CH2NO2 H2O


    Nitroethane
    4. Addition Rxn (Alkenes and Alkynes)
    •A. Hydrogenation
    •B. Halogenation
    •C. Hydrohalogenation
    A. Hydrogenation
    Pt,Pd,
    Ni
    CH2=CH2 H2 CH3CH3
    Pt,Pd,
    Ni
    CH3CH=CH2 H2 CH3CH2CH3
    Pt,Pd,
    Ni
    CH CH 2H2 CH3CH3
    Pt,Pd,
    Ni
    CH3C C ̶ CH3 2H2 CH3CH2CH2CH3
    Poisoned
    Pd
    CH3C C ̶ CH3 H2 CH3CH=CHCH3
    A. Halogenation
    CH2=CH2 Cl2 CH2 ̶ CH2 CH2ClCH2Cl
    Cl Cl

    CH3CH=CH2 Cl2 CH3CH ̶ CH2 Vicinal Dihalide

    Cl Cl
    CH3CH=CHCH3 Cl2 CH3CH ̶ CHCH3
    Cl Cl
    Cl Cl
    CH CH 2Cl2 CH ̶ CH
    Cl Cl

    Cl Cl
    CH3C C ̶ CH3 2Cl2 CH3C ̶ CCH3
    Cl Cl
    C. Hydrohalogenation
    CH2=CH2 H ̶ Cl CH3 ̶ CH2Cl CH2ClCH3

    Markovnikov’s rule
    CH3CH=CH2 H ̶ Cl CH3CH ̶ CH3
    Cl
    CH3CH=CHCH3 H ̶ Cl CH3CH2 ̶ CHCH3
    Cl
    Cl
    CH CH 2H ̶ Cl CH3 ̶ CH Geminal Dihalide

    Cl

    Cl
    CH3C C ̶ H 2H ̶ Cl CH3C ̶ CH3
    Cl
    5. Hydration of Alkene
    CH2=CH2 H ̶ OH CH3 ̶ CH2OH CH2(OH)CH3

    CH3CH=CH2 H ̶ OH CH3CH ̶ CH3


    OH
    CH3CH=CHCH3 H ̶ OH CH3CH2 ̶ CHCH3
    OH
    END
    for the Preparation and
    Properties of Alkanes, Alkenes,
    and Alkynes

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