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    Chapter 2 Alkanes

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    Shan Ti
    This document provides an overview of alkanes and organic chemistry concepts. It discusses IUPAC nomenclature rules for naming alkanes, the physical properties and structures of alkanes, and common reactions such as combustion, halogenation, and cracking. Cracking involves breaking down large alkane molecules into smaller alkanes and alkenes. Catalytic cracking uses zeolites as catalysts, while thermal cracking uses high temperatures and pressures. Cycloalkanes are also introduced as cyclic structures of alkanes that undergo similar reactions like halogenation. The objectives are to learn alkane naming and understand alkane reactions.

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    Chapter 2 Alkanes

    Uploaded by

    Shan Ti
    111 views6 pages
    This document provides an overview of alkanes and organic chemistry concepts. It discusses IUPAC nomenclature rules for naming alkanes, the physical properties and structures of alkanes, and common reactions such as combustion, halogenation, and cracking. Cracking involves breaking down large alkane molecules into smaller alkanes and alkenes. Catalytic cracking uses zeolites as catalysts, while thermal cracking uses high temperatures and pressures. Cycloalkanes are also introduced as cyclic structures of alkanes that undergo similar reactions like halogenation. The objectives are to learn alkane naming and understand alkane reactions.

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    This document provides an overview of alkanes and organic chemistry concepts. It discusses IUPAC nomenclature rules for naming alkanes, the physical properties and structures of alkanes, and common reactions such as combustion, halogenation, and cracking. Cracking involves breaking down large alkane molecules into smaller alkanes and alkenes. Catalytic cracking uses zeolites as catalysts, while thermal cracking uses high temperatures and pressures. Cycloalkanes are also introduced as cyclic structures of alkanes that undergo similar reactions like halogenation. The objectives are to learn alkane naming and understand alkane reactions.

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    111 views6 pages

    Chapter 2 Alkanes

    Uploaded by

    Shan Ti
    This document provides an overview of alkanes and organic chemistry concepts. It discusses IUPAC nomenclature rules for naming alkanes, the physical properties and structures of alkanes, and common reactions such as combustion, halogenation, and cracking. Cracking involves breaking down large alkane molecules into smaller alkanes and alkenes. Catalytic cracking uses zeolites as catalysts, while thermal cracking uses high temperatures and pressures. Cycloalkanes are also introduced as cyclic structures of alkanes that undergo similar reactions like halogenation. The objectives are to learn alkane naming and understand alkane reactions.

    Copyright:

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    Centre for Foundation Studies, UTAR

    Chapter Scopes FHSC1124 Organic Chemistry Alkanes


    Chapter 2 IUPAC Nomenclature / naming Physical properties Free-radical reactions Crude oil and cracking Cycloalkanes

    Objectives
    After this chapter, you will be able to: Name alkanes using IUPAC Draw the correct structure of simple alkanes Draw/write the product of an organic chemical reaction Understand reactions of alkanes and be able to write out the chemical reactions.

    Introduction to Alkanes
    Simplest members of hydrocarbon family Paraffins Aliphatic compounds open chain / acyclic compounds General formula of alkanes = CnH2n+2 The names of alkanes end with suffix -ane. Saturated hydrocarbon as only have CC & CH single bonds & contain the max. possible number of H per C.

    IUPAC Nomenclature
    IUPAC International Union of Pure & Applied Chemistry The IUPAC nomenclature system is a set of logical rules devised and used by organic chemists to name the organic compounds. Prefix Parent Suffix What are the How many What family? substituents? carbons?

    IUPAC Rules
    1. Select the longest continuous C chain as parent chain (use root word for the no. of C) 2. Name each of the branch/substituents as an alkyl / aryl group 3. Number the C chain begin from the end nearest to the branch branch/substituents appear at the lowest no. possible

    FHSC1124 ORGANIC CHEMISTRY

    Centre for Foundation Studies, UTAR

    IUPAC Rules
    4. Name each substituent according to its chemical identity & the no. of the C atom to which it is attached For identical substituent, use the prefix di, tri & write appropriate C no. for each substituent 5. Separate no. from no. by commas (,) & no. from letters by hyphens (-) 6. List the substituents alphabetically by name di, tri. dont count

    Base Names
    Root No. of Name Carbons (n) Meth 1 Eth 2 Prop 3 But 4 Pent 5 Root Name Hex Hept Oct Non Dec No. of Carbons (n) 6 7 8 9 10

    Straight-Chain Alkyl Groups, R


    Alkyl group Name (abbreviation) Methyl (Me) CH3 Ethyl (Et) CH2CH3 Propyl (Pr) CH2CH2CH3 Butyl (Bu) CH2CH2CH2CH3 Pentyl CH2CH2CH2CH2CH3 Alkyl groups are named by replacing the ane ending of the parent alkane with an yl ending

    Example: Naming Alkanes

    PHYSICAL PROPERTIES OF ALKANES


    Condensed structural formula
    Name Methane Ethane Propane Butane Pentane Hexane Heptane Octane Nonane Decane BP (oC) -161.7 -88.6 -42.2 -0.5 36.1 68.7 98.4 125.6 150.7 174.0 MP (oC) State at 25oC Density -182.6 Gas 0.424 -172.0 Gas 0.546 -187.1 Gas 0.582 -135.0 Gas 0.579 -129.7 Liquid 0.626 -94.0 Liquid 0.659 -90.5 Liquid 0.684 -56.8 Liquid 0.703 -53.7 Liquid 0.718 -29.7 Liquid 0.730

    Carbon skeleton
    1 2 3 4 5 6

    1. Longest continuous C chain is 6 hex 2. All C & H with single bonds ane 3. Parent name: hexane 4. Two methyl groups on 2nd C & 5th C dimethyl 5. Use 2,5-dimethylhexane

    FHSC1124 ORGANIC CHEMISTRY

    Centre for Foundation Studies, UTAR

    Boiling Points of Alkanes


    Alkanes have relatively low bp (e.g.: methane bp~ -161 oC) because: Alkanes are ____________ molecules which held by _____________________________. BP of alkanes increase as number of carbon increase because: As the number of C , molecules get ______, Van der Waals forces become ___________ and more energy needed to break the bond

    Comparison of BP: Branched-Chain & Straight-Chain


    Isomer pentane 2-methylbutane 2,2-dimethylpropane BP (K) 309.2 301.0 282.6

    The more branched the chain, the _______ the boiling point tends to be.

    Comparison of BP: Branched-Chain & Straight-Chain


    The branched-chain isomer will have a lower bp compared to the straight-chain isomer because: Branched-chain alkanes are short, fat & spherical in shape. Thus this reduces the surface area that is exposed to Van der Waals forces. Less energy needed, bp decreases.

    Reaction of Alkanes

    Combustion / oxidation of Alkanes

    Free Radical Halogenation

    1. Combustion / Oxidation of Alkanes


    Alkanes burn in excess air or O2, to formed CO2 and H2O CxHy +
    y x + O 4 2 4

    2. Free Radical Halogenation of Alkanes


    Alkanes react with chlorine or bromine: When the mixture is heated at 300 400 oC, OR At room temperature under the influence of UV light which act as catalysts.

    xCO2 +
    4

    y 2

    H2O

    CH4 + 1 + 4 O2 CO2 + 2 H2O CH4 + 2O2 CO2 + 2H2O

    XX + Halogens

    light / heat X = Br, Cl

    X + HX

    Haloalkanes / alkyl halides

    FHSC1124 ORGANIC CHEMISTRY

    Centre for Foundation Studies, UTAR

    Chlorination of Methane

    Mechanism of Halogenation
    Chlorination or bromination of alkanes is by a free-radical substitution mechanism. Involved 3 steps: Step 1: Initiation Step 2: Propagation Step 3: Termination

    Mechanism of Halogenation: Step 1: Initiation


    Heat or UV light cause the weak halogen bond to undergo ____________ cleavage to generate two bromine radicals and starting the chain process.

    Mechanism of Halogenation: Step 2: Propagation


    (a) Br radical abstracts a H to form HBr and a methyl radical (b) The methyl radical abstracts a Br atom from another molecule of Br2 to form the methyl bromide and another bromine radical, which can then itself undergo reaction 2(a) creating a cycle that can repeat.

    Mechanism of Halogenation: Step 2: Propagation

    Mechanism of Halogenation: Step 3: Termination


    Various reactions between possible pairs of radicals allow the formation of ethane, Br2 or the product, methyl bromide. These reactions remove radicals and do not perpetuate the cycle.

    (a)

    (b)

    FHSC1124 ORGANIC CHEMISTRY

    Centre for Foundation Studies, UTAR

    Crude Oil / Petroleum


    Alkanes occur naturally in petroleum and natural gas. Petroleum, brownish to black liquid, formed from dead organisms that sank to the bottom shallow seas and were subsequently covered by clay & silt. Pressure heating caused by burial changed these organic matter slowly, after million years, to petroleum. Raw petroleum consists of a mixture of hydrocarbon of various sizes separated by distillation before they used.

    Cracking of Alkanes
    Cracking involves the _____________ of large alkane molecules into a mixture of smaller-sized alkanes and alkenes.

    Cracking of Alkanes

    Cracking of Alkanes Catalytic Cracking Thermal/Steam Cracking

    Catalytic Cracking
    Modern cracking uses zeolites as the _____________. Zeolites = complex aluminosilicates, and are large lattices of aluminium, silicon and oxygen atoms carrying a negative charge. The alkane is brought into contact with the catalyst at a T of about 500 and C moderately low P.

    Thermal / Steam Cracking


    In thermal cracking, high T (typically in the range of 450 to 750 & P (up to C C) about 70 atm) are used to break the large hydrocarbons into smaller ones. Thermal cracking gives mixtures of products containing high proportions of hydrocarbons with double bonds alkenes.

    FHSC1124 ORGANIC CHEMISTRY

    Centre for Foundation Studies, UTAR

    Cycloalkanes: Cyclic Structures of Alkanes

    Halogenation of Cycloalkanes
    The reactions of the cycloalkanes are generally just the same as the alkanes, e.g. free radical substitution, oxidation & halogenation.

    + Br2

    Br + HBr

    Summary
    To learn the naming of alkanes Understand reactions of alkanes and be able to write out the chemical reactions.

    FHSC1124 ORGANIC CHEMISTRY

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