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    Organic Chemistry: Outline

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    Shaker Mahmood
    The document outlines the key topics in Organic Chemistry Lecture 3: 1. It discusses the physical properties, preparation methods, and chemical reactions of alkanes. Alkanes are nonpolar, have low boiling points, and are generally inert except for halogenation and combustion reactions. 2. Preparation of alkanes is described through hydrogenation of alkenes, reduction of alkyl halides, and coupling of alkyl halides. 3. Chemical reactions of alkanes include substitution reactions like halogenation, combustion, isomerization, reactions with steam, and pyrolysis at high temperatures.

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    Organic Chemistry: Outline

    Uploaded by

    Shaker Mahmood
    73 views12 pages
    The document outlines the key topics in Organic Chemistry Lecture 3: 1. It discusses the physical properties, preparation methods, and chemical reactions of alkanes. Alkanes are nonpolar, have low boiling points, and are generally inert except for halogenation and combustion reactions. 2. Preparation of alkanes is described through hydrogenation of alkenes, reduction of alkyl halides, and coupling of alkyl halides. 3. Chemical reactions of alkanes include substitution reactions like halogenation, combustion, isomerization, reactions with steam, and pyrolysis at high temperatures.

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    The document outlines the key topics in Organic Chemistry Lecture 3: 1. It discusses the physical properties, preparation methods, and chemical reactions of alkanes. Alkanes are nonpolar, have low boiling points, and are generally inert except for halogenation and combustion reactions. 2. Preparation of alkanes is described through hydrogenation of alkenes, reduction of alkyl halides, and coupling of alkyl halides. 3. Chemical reactions of alkanes include substitution reactions like halogenation, combustion, isomerization, reactions with steam, and pyrolysis at high temperatures.

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    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    73 views12 pages

    Organic Chemistry: Outline

    Uploaded by

    Shaker Mahmood
    The document outlines the key topics in Organic Chemistry Lecture 3: 1. It discusses the physical properties, preparation methods, and chemical reactions of alkanes. Alkanes are nonpolar, have low boiling points, and are generally inert except for halogenation and combustion reactions. 2. Preparation of alkanes is described through hydrogenation of alkenes, reduction of alkyl halides, and coupling of alkyl halides. 3. Chemical reactions of alkanes include substitution reactions like halogenation, combustion, isomerization, reactions with steam, and pyrolysis at high temperatures.

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    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    of 12

    Organic chemistry

    lecture 3
    Email: [email protected]

    Outline
    • Physical properties of alkanes
    • Preparation of alkane
    • Chemical reaction ( properties) of alkane
    Physical properties of alkanes
    • Alkanes are almost non-polar molecules because of the covalent
    nature of C-C and C-H bonds and due to very little difference of
    electronegativity between carbon and hydrogen atoms.
    • They possess weak van der Waals forces.
    • Due to the weak forces, the first four members, C1 to C4 are
    gases, C5 to C17 are liquids and those containing 18 carbon
    atoms or more are solids at 298 K.
    • Odorless or mild odor, colorless, tasteless, nontoxic
    • Flammable, otherwise not very reactive
    • Alkanes have low bp’s and mp’s compared to more polar compounds
    of comparable size.
    Preparation of alkane :
    1- Hydrogenation of alkenes:
    H2\ Pd, Pt or Ni
    CnH2n CnH2n+2
    Alkene alkane

    CH3CH=CHCH3 H2\ Pt
    CH3CH2CH2CH3
    2- Butene
    A catalyst (Pd, Pt or Ni) bring about addition of molecular hydrogen, H2 to the
    double bond.
    2- Reduction of alkyl halides:
    A- Hydrolysis of Grignard reagent: the Grignard reagent has the general
    formula RMgX and the general name alkyl magnesium.
    dry ether
    RX + Mg RMgX
    alkyl halide alkyl magnesium halide
    The Grignard reagent is highly reactive. It reacts with inorganic compounds including
    H2O, CO2, O2 and many organic compounds.
    RMgX + HOH → R-H + Mg(OH)X
    Stronger acid weaker acid
    Any compound containing attached to oxygen or nitrogen is more acidic than an alkane: for
    example NH3 or methyl alcohol.
    RMgX + NH3 → R-H + Mg(NH2)X
    RMgX + CH3OH → R-H + Mg(OCH3)X
    Stronger acid weaker acid

    H 2O
    CH3CH2Cl + Mg dry ether CH3CH2MgCl CH3CH3 + Mg(OH)Cl

    H2 O
    CH3CHCl + Mg dry ether CH3CHMgCl CH3CH2CH3 + Mg(OH)Cl
    CH3 CH3

    B- Reduction by metal and acid:


    RX + Zn + H+ RH + Zn+2 + X-
    CH3CH2CHCH3 Zn + H+ CH3CH2CH2CH3
    Br n-butane
    2- bromo butane
    3- Coupling of alkyl halides with organic metallic compounds:
    Alkyl halide may be 1º, 2º, 3º.
    CH3X RCH2X R2CHX CR3X
    Methyl alkyl 1º 2º 3º
    One R group two R group three R group
    To make an alkane of higher carbon number then the starting material
    requires formation of carbon-carbon bonds, most directly by the
    coupling together of two alkyl groups.
    CuX
    RX + Li RLi R-Cu-Li
    R
    Alkyl halide alkyl lithium coprous halide lithium dialkyl copper

    R-Cu-Li + R X R-R + RCu + LiX


    alkane
    R
    R` may be the same as or different from R, R = R` or R ≠ R
    Example : 1.prepare 3-methyle hexane from methyl chloride

    Exercises
    Starting with alkyl halides containing no more than four carbon atoms,
    how would you synthesize each of the following alkanes?
    2,5-dimethylhexane
    2-methylhexane
    Chemical reaction ( properties) :
    As already mentioned, alkanes are generally inert towards acids, bases,
    oxidising and reducing agents. However, they undergo the following
    reactions under certain conditions.
    Substitution reactions: One or more hydrogen atoms of alkanes can be
    replaced by halogens, nitro group and sulphonic acid group.

    Halogenation:
    In the presence of light or heat, alkanes react with halogens to form alkyl
    halides. Halogenation is a radical substitution reaction, because a
    halogen atom X replaces hydrogen via a mechanism that involves radical
    intermediates. X substitutes for H

    h or heat
    - C - H + X2 -C - X + HX X=Cl or Br
    alkyl halide
    When CH4 is treated with excess Cl2, all four hydrogen atoms can be
    successively replaced by Cl to form CCl4.

    CH4 Cl2 CH3Cl Cl2 CH2Cl2 Cl2 CHCl3 Cl2 CCl4


    h + HCl h + HCl h + HCl h +HCl

    Example: draw all the constitutional isomers formed by


    monohalogenation of (CH3)2CHCH2CH3 with Cl2 and hν. For you ::??

    A radical: is a reactive intermediate with a single unpaired electron


    formed by hemolysis of a covalent bond.
    A─ B → A• + B• radicals
    2. Combustion: alkanes on heating in the presence of air or dioxygen
    are completely oxidized to carbon dioxide and water with the evolution
    of large amount of heat.

    flame
    CnH2n +2 + O2 nCO2 + (n+1) H2O + heat
    excess
    flame 5CO2 + 6H2O H= -845Kcal
    C5H12 + 8O2
    heat of combustion

    3.Isomerisation: n-alkanes on heating in the presence of anhydrous


    aluminum chloride and hydrogen chloride gas isomerizes to branched
    chain alkane.
    4. Reaction with steam: Methane reacts with steam at 1273 K in the
    presence of nickel catalyst to form carbon monoxide and dihydrogen.
    This method is used for industrial preparation of dihydrogen gas

    5.Pyrolysis: higher alkanse on heating to higher temperature


    decompose into lower alkanes, alkenes etc. Such a decomposition
    reaction into smaller fragments by the application of heat is called
    pyrolysis or cracking

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