Chapter 3 Alkenes(1)

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    ORGANIC CHEMISTRY

    CHM 207

    CHAPTER 3:

    ALKENES

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    Subtopics

    Nomenclature

    Structures and

    physical

    properties

    Preparation ofalkenes

    Reactions of

    alkenes

    Addition

    Combustion

    Oxidation

    Polimerization

    Unsaturation

    tests

    Uses

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    Also called olefins

    Contain at least one carbon-carbon double bond

    C=C)

    General formula, Cn

    H

    2n

    n=2,3,)

    Classified as unsaturated hydrocarbons

    compound with double or triple carbon-carbon

    bonds that enable them to add hydrogen atoms.

    sp2

    -hybridized

    For example:

    C

    2

    H

    4

    - ethylene

    CH2 CH2

    ALKENES

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    RULE 1. Select the longest continuous carbon chain that

    contains a double bond.

    This chain

    contains 6 C

    atoms

    This chain

    contains 8C atoms

    - The chain contain 8 C, therefore, name the parent

    compound octene.

    correctwrong

    RULE 2. Name this compound as you would an alkane, but

    change

    n

    to

    n

    for an alkene.

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    RULE 3. Number the carbon chain starting with the endnearer to the double bond.

    Use the smaller numbes on the double-bonded carbon to

    indicate the position of the double bond. Place this number

    in front of the alkene name.

    This end of the chain is closest to the

    double bond. Begin numbering here.

    1234

    8

    7

    6

    5

    The name of the parent

    compound is 1-octene.

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    RULE 4. Branched chains and other groups are treated as innaming alkanes. Name the substituent group, and

    designate its position on the parent chain with a number.

    8

    7

    3 2 1

    6

    5

    The ethyl group is attached to carbon 4.

    4

    4-ethyl-1-octene

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    Placing numbers location of double bond) before the

    part of the name n .

    Example:

    CH2 C CH2

    H

    Old naming system: 1-buteneNew naming system: but-1-ene

    1 2 3 4CH3 C C CH2

    H H

    1 2 3 4CH2 CH35 6

    Old naming system: 2-hexeneNew naming system: hex-2-ene

    CH2 C C CH3H H

    Old naming system: 3-methyl-1-buteneNew naming system: 3-methylbut-1-ene

    1 2 4

    CH3

    CH3

    3

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    A compound with more than one double bond.

    - Two double bond: diene

    -Three double bond: triene

    - Four double bond: tetraene

    * Numbers are used to specify the locations of the double

    bonds.

    CH2 C C CH2H H

    IUPAC names: 1,3-butadiene 1,3,5-heptatriene

    new IUPAC names: buta-1,3-diene hepta-1,3,5-triene

    1 2 3 4

    CH3 C C C C C CH2

    12347 6 5

    H H H H H

    1 23

    47

    6 5

    8

    IUPAC names: 1,3, 5, 7-cyclooctatetraene

    new IUPAC names: cycloocta-1,3,5,7-tetraene

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    Alkenes names as substituents are called

    lk nyl

    groups.

    Can be named systematically as ethenyl, propenyl, etc.

    or by common names such as vinyl, ally, methylene and

    phenyl groups.

    CH2 -CH=CH2

    CHCHCH2CHCH2 CH2

    CH=CH2

    IUPAC name: 3-vinyl-1,5-hexadiene

    -CH2-CH=CH2

    methylene group(methylidene group)

    vinyl group(ethenyl group)

    3-methylenecyclohexene

    New IUPAC name: 3-vinylhexa-1,5-diene

    allyl group(2-propenyl group)

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    Contains C=C in the ring

    CH3 CH2CH31

    2

    34

    5

    6

    1

    23

    4

    5

    1-methylcyclohexene 1,5-dimethylcyclopentene

    12

    34

    5

    6

    IUPACname: 2-ethyl-1,3-cyclohexadieneNew IUPACname: 2-ethylcyclohexa-1,3-diene

    cyclopropene cyclobutene cyclohexenecyclopentene

    Nomenclature of cycloalkenes:- Similar to that alkenes

    - Number the cycloalkane so that the double bond is between C1 and

    C2 and so that the first substituent has as low a number as possible.

    * Double bond always between C1 and C2.

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    c is two particular atoms (or groups of atoms) are

    adjacent to each other

    t rans the two atoms (or groups of atoms) are

    across from each other

    C CH3C

    H

    CH2CH3

    H

    C CH3C

    H

    H

    CH2CH3

    cis-2-pentene trans-2-pentene

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    i) boiling points and densities

    ii)polarity

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    - Most physical properties of alkenes are similar to thosealkanes.

    - Example: the boiling points of 1-butene, cis-2-butene, trans-2-butene and n-butane are close to 0oC.

    - Densities of alkenes: around 0.6 or 0.7 g/cm3.

    - Boiling points of alkenes increase smoothly with molecularweight.

    - Increased branching leads to greater volatility and lowerboiling points.

    i. Boiling points and densities

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    - relatively nonpolar.

    - insoluble in water but soluble in non-polar solvents suchas hexane, gasoline, halogenated solvents and ethers.

    - slightly more polar than alkanes because:

    i) electrons in the pi bond is more polarizable(contributing to instantaneous dipole moments).

    ii) the vinylic bonds tend to be slightly polar

    (contributing to a permanent dipole moment).

    ii. Polarity

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    Alkyl groups are electron donating toward double bond,helping to stabilize it. This donating slightly polarizes thevinylic bond, with small partial positive charge on the alkyl

    group and a small negative charge on the double bond carbonatom.

    For example, propene has a small dipole moment of 0.35 D.

    propene, = 0.35 D

    C C

    H3C

    H

    H

    H

    C C

    H3C

    H

    CH3

    H

    C C

    H3C

    H

    H

    CH3

    Vector sum =

    propene, = 0.33 D

    cis-2-butene, bp 4oC

    Vector sum = 0

    propene, = 0

    trans-2-butene, bp 1oC

    Vinylic bonds

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    In a cis-disubstituted alkene, the vector sum of the two dipolemoments is directed perpendicular to the double bond.

    In a trans-disubstituted alkene, the two dipole moments tend tocancel out. If an alkene is symmetrically trans-disubstituted, thedipole moment is zero.

    Cis- and trans-2-butene have similar van der Waals attractions, butonly cis isomer has dipole-dipole attractions.

    Because of its increased intermolecular attractions, cis-2-butenemust be heated to a slightly higher temperature (4oC versus 1oC)before it begins to boil.

    C C

    H3C

    H

    CH3

    H

    C C

    H3C

    H

    H

    CH3

    Vector sum =

    propene, = 0.33 D

    cis-2-butene, bp 4oC

    Vector sum = 0

    propene, = 0

    trans-2-butene, bp 1oC

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    i) dehydration of alcohols

    ii) dehydrohalogenation of haloalkanes

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    Alkenes can be prepared in the following ways:

    conc. H2SO4R-CH2-CH2-OH R-CH=CH2 + H2O

    NaOH/ethanolR-CH

    2

    -CH2

    -Xreflux R-CH=CH2 + HX

    NaOH can be replaced by KOH

    i. Dehydration of alcohols

    ii. Dehydrohalogenation of haloalkanes

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    Saytzeff rule:

    - A reaction that produces an alkene would favour the

    formation of an alkene that has the greatest number ofsubstituents attached to the C=C group.

    CH3CH2-CH-CH3OH

    H+

    H+

    CH3CH=CH-CH3 + H2O

    CH3CH2-CH=CH2 + H2O

    2-butanol2-butenemajor product

    1-butene

    CH3CH-CH-CH2

    BrH H

    KOH CH3CH=CH-CH3 CH3CH2CH=CH2alcohol

    reflux

    2-bromobutane2-butene(major product)

    1-butene

    Dehydration of alcohols

    Dehydrohalogenation of haloalkanes

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    Alkenes are more reactive than alkanes because:

    i) A carbon-carbon double bond consists of a and a bond. It is

    easy to break the bond while the bond remains intact.

    ii) The electrons in the double bond act as a source of electrons(Lewis base). Alkenes are reactive towards electrophiles which

    are attracted to the negative charge of the electrons.

    iii) bond will broken, each carbon atom becomes an active site

    which can form a new covalent bond with another atom. One bond is converted into 2 bonds.

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    i) Addition reaction:

    a) Addition of hydrogen (Catalytic hydrogenation)

    b) Addition of halogens

    - In inert solvent

    - In water / aqueous medium

    c) Addition of hydrogen halides

    d) Addition reaction with concentrated sulfuric acid: hydration of

    alkenes

    e) Addition reaction with acidified water (H3O+): hydration of alkenes

    ii) Combustion of alkenes

    iii) Oxidation:a) Epoxidationb) Hydroxylationc) Ozonolysis

    iv) Polymerization

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    a) Addition of hydrogen (Catalytic hydrogenation):- hydrogenation: addition of H to a double bond and triple bond to

    yield saturated product.

    - alkenes will combine with hydrogen in the present to catalyst to

    form alkanes.

    C C H H C C

    H H

    Pt or Pd

    25-90o

    C

    - Plantinum (Pt) and palladium (Pd) Catalysts

    - Pt and Pd: temperature 25-90oC

    - Nickel can also used as a catalyst, but a higher temperature of 140oC

    200oC is needed.

    i) Addition reaction

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    H2C CH2 H2Pt

    CH3CH2CH2CH2CH CH2 H2Pt

    H3C CH3

    CH3CH2CH2CH2CH2CH3

    EXAMPLES:

    ethylene ethanelow pressure

    low pressurehexene hexane

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    b) Addition of halogens:

    i) In inert solvent:- alkenes react with halogens at room temperature and in dark.

    - the halogens is usually dissolved in an inert solvent such as

    dichloromethane (CH2Cl2) and tetrachloromethane (CCl4).

    - Iodine will not react with alkenes because it is less reactive than

    chlorine and bromine.

    - Fluorine is very reactive. The reaction will produced explosion.

    C C X X C C

    X X

    inert solvent

    X X = halogen such as Br2or Cl2Inert solvent = CCl4or CH2Cl2

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    EXAMPLES:

    C CHH

    H H Br Br

    Br2

    Br

    Br

    CCl4

    CH3CH=CH2 Cl2CCl4

    CH3CH

    Cl

    CH2

    Cl

    C C

    Br

    H H

    Br

    H Hinert solvent (CCl4)

    ethene1,2-dibromoethane

    * the red-brown colour of the bromine solution will fade and the

    solution becomes colourless.

    cyclohexene 1,2-dibromocyclohexane

    propene 1,2-dichloropropane

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    b) Addition of halogens:

    ii) In water / aqueous medium:

    - chlorine dissolves in water to form HCl and chloric (l) acid

    (HOCl).

    Cl2 (aq) + H2O(l) HCl(aq) + HOCl (aq)

    - same as bromine

    Br2 (aq) + H2O(l) HBr(aq) + HOBr(aq)

    * Reaction of alkenes with halogens in water/ aqueous solution (eg.chlorine water and bromine water) produced halohydrins (an alcohol

    with a halogen on the adjacent carbon atom).

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    EXAMPLES:

    CH3CH=CH2 + Br2H2O

    CH3 CH

    OH

    CH2Br

    CH3 CH

    Br

    CH2Br

    1-bromo-2-propanol

    (major product)

    1,2-dibromopropane

    (minor product)

    propene

    * Br atom attached to the carbon atom of the double bond which has the greater

    number of hydrogen atoms.

    CH3 CH2

    1-chloro-2-butanol1-butene

    CH3CH2CH=CH2 CH

    OH

    CH2

    Cl

    Cl2, H2O

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    c) Addition of hydrogen halides:

    - Addition reaction with electrophilic reagents.

    - Alkenes react with hydrogen halides (in gaseous state or in aqueous

    solution) to form addition products.

    - The hydrogen and halogen atoms add across the double bond to

    form haloalkanes (alkyl halides).

    - General equation:

    C C C C

    H XHX

    alkene haloalkane

    - Reactivity of hydrogen halides : HF < HCl < HBr < HI

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    * Reaction with HCl needs a catalyst such as AlCl3

    H2C CH2 HCl AlCl3

    CH3CH2Cl

    H-I

    CH3CH=CHCH3 + H-Br

    I

    CH3CH2CHCH3

    Br

    EXAMPLES:

    cyclopentene iodocyclopentane

    2-butene 2-bromobutane

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    There are 2 possible products when hydrogen halides react with anunsymmetrical alkene.

    It is because hydrogen halide molecule can add to the C=C bond in

    two different ways.

    C CH

    HCH3H

    H-I

    C C

    H

    HCH3

    H

    H-I

    C CH

    HCH3H

    H I

    C C

    H

    HCH3

    H

    I H

    1-iodopropane

    2-iodopropane(major product)

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    Markovnikovs rules:

    - the addition of HX to an unsymmetrical alkene,the hydrogen atom adds to the carbon atom (ofthe double bond) that already has the greaternumber of hydrogen atoms.

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    Step 2: Rapid reaction with a negative ion.

    The negative ion (Y-) acts as nucleophile and attacks the positively

    charged carbon atom to give product of the addition reaction.

    C C

    E

    Y-

    C C

    E Y

    Mechanism of electrophilic addition reactions:

    - C=C : electron rich part of the alkene molecule

    - Electrophiles: electron-seeking

    Step 1: Formation of carbocation.

    Attack of the pi bond on the electrophile to form carbocation.

    C C C C

    E

    E Y Y-

    carbocation

    + -

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    CH3CH=CH2 HCl

    CH3CHCH2

    H Cl

    CH3CHCH2

    Cl H

    1-chloropropane

    2-chloropropane(major product)

    according to Markovnikovsrules

    123

    Propene

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    MECHANISM:

    Step 1: Formation of carbocation

    CCH H

    HCH3H Cl CC

    H HHC

    H

    HH

    H

    CC

    H H

    HCH

    H

    H H

    or

    less stable carbocation

    (1o

    carbocation)

    more stable carbocation

    (2o

    carbocation)

    Cl-

    - 2o carbocation is more stable than 1o carbocation.

    - 2o

    carbocation tends to persist longer, making it more likely to combine with

    Cl-

    ion to form 2-chloromethane (basis of Markovnikov's rule).

    CC

    H H

    HCH

    H

    H H

    Cl-

    Step 2: Rapid reaction with a negative ion

    CC

    H H

    HCH

    H

    H HCl

    2-chloromethane (major product)

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    d) Addition reaction with concentrated sulfuric acid: hydration of

    alkenes

    - the alkene is absorbed slowly when it passed through

    concentrated sulfuric acid in the cold (0-15oC).

    - involves the addition of H atom and HSO4 group across the

    carbon-carbon double bond.

    - follows Markovnikovs rule.

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    C C H

    HH

    H H OSO3H

    (H2SO4)

    CH3CH2OSO3H+H-OH

    (H2O)

    C C H

    HH

    H

    H OSO3H

    CH3CH2OH +H2SO4

    ethyl hydrogensulphate

    (CH3CH2HSO4)

    When the reaction mixture is added to water and warmed,

    ethyl hydrogensulphate is readily hydrolysed to ethanol

    *ethene reacts with concentrated H2

    SO4

    to form ethanol*

    or

    *alkene reacts with concentrated H2SO4to form alcohol*

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    e) Addition reaction with acidified water (H3O+): hydration of alkenes

    Hydration: The addition of H atoms and OH groups from watermolecules to a multiple bond.

    Reverse of the dehydration reaction.

    Direct hydration of ethene:

    - passing a mixture of ethene and steam over phosphoric (v) acid

    (H3PO4) absorbed on silica pellets at 300oC and a pressure of 60

    atmospheres.

    - H3PO4 is a catalyst.

    CH2=CH2 H2OH3PO4

    CH3CH2OH(g) (g)

    300

    o

    C, 60 atm

    (g)

    ethene ethanol

    C C H2O C C

    H OH

    alkene alcohol

    H+

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    Markovnikovs rule is apply to the addition of a water molecule

    across the double bond of an unsymmetrical alkene.

    For examples:

    CH3 C CH2

    CH3

    H OH H+

    CH3CH=CH2 + H2O CH3CHCH3

    OH

    CH3 C CH2

    CH3

    OH H

    25o

    C2-methylpropene

    tert-butyl alcohol

    propene

    2-propanol

    H+

    H+ = catalyst

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    CCH H

    HCH3

    CC

    H H

    HCH

    H

    H H

    H+

    OH

    H

    CH3CHCH3

    O H

    H

    CH3CHCH3

    OH

    CC

    H H

    HCH

    H

    H H

    CH3CHCH3

    O H

    H

    H+

    MECHANISM OF ACID CATALYSED HYDRATION OF ALKENES

    Step 1: Protonation to form carbocation

    more stable carbocation

    (2o

    carbocation)

    Step 2: Addition of H2O to form a protonated alcohol

    Step 3: Loss of a proton (deprotonated) to form alcohol

    H+ = catalyst

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    When HBr is added to an alkene in the absence of peroxides it obey

    Markovnikovs rule.

    When HBr (not HCl or HI) reacts with unsymmetrical alkene in the

    presence of peroxides (compounds containing the O-O group) or

    oxygen, HBr adds in the opposite direction to that predicted byMarkovnikovs rule.

    The product between propene and HBr under these conditions is 1-

    bromopropane and not 2-bromopropane.

    CH3CH=CH2 HBr CH3CH2CH2Brperoxide

    1-bromopropane(major product)

    anti-Markovnikovs orientation

    ANTI-MARKOVNIKOVS RULE: FREE RADICAL

    ADDITION OF HYDROGEN BROMIDE

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    Anti-Markovnikovs addition:

    - peroxide-catalysed addition of HBr occurs through afree radical addition rather than a polar electrophilicaddition.

    - also observed for the reaction between HBr andmany different alkenes.

    - not observed with HF, HCl or HI.

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    Alkenes goes to hydroboration reaction to form anti-

    Markovnikov alcohol.

    C C

    CH3 C

    CH3

    CH2

    CH3CH=CH2

    CH C

    CH3

    CH3CH3

    B2H6

    B2H6

    B2H6

    B2H6

    C C

    OHH

    CH3 CH

    CH3

    CH2 OH

    CH3CHCH2-OH

    CH3CHCHCH3

    OH

    CH3

    H2O2,-

    OH

    anti-markovnikov

    examples:

    H2O2, -

    OH

    propene propanol

    H2O2,-

    OH

    isobutylene isobutyl alcohol

    H2O2,-

    OH

    3-methyl-2-butanol

    2-methyl-2-butene

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    The alkenes are highly flammable and burn readily

    in air, forming carbon dioxide and water.

    For example, ethene burns as follows :

    C2H4 + 3O2 2CO2 + 2H2O

    ii) Combustion of alkenes

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    Oxidation: reactions that form carbon-oxygen bonds.

    Oxidation reaction of alkenes:

    a) Epoxidation

    b) Hydroxylationc) Ozonolysis

    iii) Oxidation

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    Epoxide / oxirane: a three-membered cyclic ether.

    CH3 C

    O

    peroxyacetic acid

    O O H C

    O

    peroxybenzoic acid

    (PhCO3H)

    O O H

    m-chloroperoxybenzoic acid

    (MCPBA)

    Cl O

    O

    O

    H

    C CR C

    O

    O O H

    O

    C C R C

    O

    OH

    alkene

    peroxyacid epoxide (oxirane) acid

    Examples of epoxidizing reagent:

    a) Epoxidation of alkenes

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    MCPBA

    MCPBA

    O

    OCH2CI2, 25

    oC

    cyclohexene 1,2-epoxycyclohexane

    CH2CI2, 25o

    C

    cycloheptene 1,2-epoxycycloheptane

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    Hydroxylation:- Converting an alkene to a glycol requires adding a hydroxyl

    group to each end of the double bond.

    Hydroxylation reagents:

    i) Osmium tetroxide (OsO4

    )

    ii)Potassium permanganate (KMnO4)

    C C OsO4 H2O2 C C

    OHOH(or KMnO4,-

    OH)

    glycol

    b) Hydroxylation of alkenes

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    CH CH2CH3

    CH2 CH2 CH2 CH2

    OH OH

    CH2

    OH

    CHCH3

    OH

    MnO2

    MnO2

    KMnO4(aq), OH-

    cold, dilute

    ethene

    1,2-ethanediol

    KMnO4(aq), OH-cold, dilute

    propene

    1,2-propanediol

    * Also known as Baeyers test

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    Ozonolysis:- The reaction of alkenes with ozone (O3) to form an ozonide, followed byhydrolysis of the ozonide to produce aldehydes and /or ketone.

    - Widely used to determine the position of the carbon-carbon double bond.

    - Ozonolysis is milder and both ketone and aldehydes can be recoveredwithout further oxidation.

    C C

    R

    R

    R'

    HO3 C

    O OC

    O R'

    H

    R

    R

    (CH3)2S

    C O

    R

    RCO

    R'

    Hozonide ketone aldehyde

    or H2O, Zn/H+

    c) Ozonolysis of alkenes

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    H

    OCH3CH3O

    H

    H

    O

    OOCH3

    H

    O

    CH3O

    O

    H

    O

    H

    Oi) O3

    ii) (CH3)2S3-nonene

    i) O3

    ii) (CH3)2S

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    Polymer: A large molecule composed of many smaller repeating units(the monomers) bonded together.

    Alkenes serves as monomers for some of the most common polymerssuch as polyethylene (polyethene), polypropylene, polystyrene,poly(vinyl chloride) and etc.

    Undergo addition polymerization /chain-growth polymer:

    - a polymer that results from the rapid addition of one molecule at atime to a growing polymer chain, usually with a reactive intermediate(cation, radical or anion) at the growing end of the chain.

    iv) Polymerization of alkenes

    C C

    CI

    H

    H

    H

    C C

    CI

    H

    H

    H

    C C

    CI

    H

    H

    H

    C C

    CI

    H

    H

    H

    C

    H

    H

    C

    Cl

    H

    C

    H

    H

    C

    Cl

    Hn

    poly(vinyl chloride)vinyl chloride

    repeating unit

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    POLYMER POLYMER USES MONOMER

    FORMULA

    POLYMER

    REPEATING UNIT

    Polyethylene Bottles, bags,

    films

    Polypropylene Plastics, olefin

    fibers

    Polystyrene Plastics, foam

    insulation

    Poly isobutylene) Specialized

    rubbers

    CH2=CH2 CH2 CH2 n

    CH2 CH

    CH3

    n

    C CH

    H

    CH3

    H

    CH2 C

    CH3

    CH3

    nC CCH3

    CH3

    H

    H

    H2

    C CH n

    C C

    H

    H H

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    i) Reactions of alkenes with KMnO4

    ii) Reactions of alkenes with bromine.

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    - KMnO4 is a strong oxidizing agent.

    - alkenes undergo oxidation reactions with KMnO4

    solution under two conditions:

    a) Mild oxidation conditions using cold, dilute,

    alkaline KMnO4 (Baeyers test).

    b) Vigorous oxidation conditions using hot,acidified KMnO4.

    UNS TUR TION TESTS FOR LKENES

    i) Reaction of alkenes with KMnO4

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    a) Reaction of alkenes with cold, dilute, alkaline KMnO4 (Baeyerstest)

    - the purple colour of KMnO4 solution disappears and a cloudybrown colour appears caused by the precipitation of manganese(IV) oxide, MnO2.

    - test for carbon-carbon double or triple bonds.

    - a diol is formed (containing two hydroxyl groups on adjacent

    carbon atoms).

    C C C C

    O H O H

    M nO 2K M n O 4 (aq), OH

    -

    cold, d ilute

    a diol

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    - A solution of bromine in inert solvent (CH2

    CI2

    or CCI4

    ) and dilutebromine water are yellow in colour.

    - The solution is decolorised when added to alkenes or organiccompounds containing C=C bonds.

    C C Br2 CH 2CI 2

    C C Br2(aq) H2O

    C C

    Br Br

    C C

    O H B r

    C C

    Br Br

    ii) Reaction of alkenes with bromine

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    a) Ozonolysis of alkenes:

    - For example, ozonolysis of an alkene produces

    methanal and propanone.

    C O

    methanal

    HH CO CH3

    CH3

    propanone

    C

    H

    H C CH3

    CH3

    CC CH3

    CH3H

    H

    remove the oxygen atoms from the carbonyl compounds and

    joining the carbon atoms with a double bond.

    2-methylpropene

    DETERMIN TION OF THE POSITION OF THE

    DOUBLE BOND

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    b) Reaction of alkenes with hot, acidified KMnO4

    - by using hot, acidified KMnO4, the diol obtained isoxidised further.

    - cleavage of carbon-carbon bonds occurs and the finalproducts are ketones, carboxylic acids or CO2.

    KMnO4/H+

    C CH2

    CH3

    CH3C O

    CH3

    CH3 CO2 + H2O2-methylpropene

    propanone

    (ketone)

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    Example:

    An alkene with the molecular formula C6H12 is oxidised with hot

    KMnO4 solution. The carboxylic acids, butanoic acid(CH3CH2CH2COOH) and ethanoic acid (CH3COOH), are produced.

    Identify the structural formula of the alkene.

    C C

    H

    R

    H

    R'

    CH3CH2CH2COOH and CH3COOH

    C O

    OH

    R CO

    OH

    R'

    CH3CH2CH2CH=CHCH3

    KMnO4/H+

    i) cleavage of the double bond gives a mixture of carboxylic acids

    ii) location of the double bond is done by taking away the oxygen atoms from the

    carboxylic acids and then joining the carbon atoms by the double bond.

    RCOOH and R'COOH RCH=CHR'

    butanoic acid ethanoic acid 2-hexene

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    C CR

    R''

    R'

    HC C H

    R'R

    OH

    R''

    OH

    KMnO4/H+

    C O

    R

    R'' COH

    R'C O

    R

    R'' CO OH

    R'

    ketone acid ketone aldehyde

    Example:

    KMnO4/H+

    CO

    O

    CHO

    4-methyl-4-octene 2-pentanone butanoic acid

    R CH=CH2KMnO4/H

    +

    R COOH + CO2+ H2O

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    i) PE

    ii) PVC

    iii) ethanol

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    Ethylene and propylene are the largest-volume industrial organic

    chemicals. Used to synthesis a wide variety of useful compounds.

    CH3 C

    O

    OH

    CH2 CH2

    CI CI

    Cl2C C

    H

    H

    H

    H

    CH3 C

    O

    H

    O2

    C C

    CIH

    H H

    CH3 CH2

    OH

    NaOH

    C C

    H H

    HH

    H+

    H2O

    CH2 CH2

    OHOH

    O

    H2C CH2

    n

    polyethylene

    polymerize

    acetaldehyde

    oxidize

    oxidize

    acetic acid

    ethylene ethylene dichloride

    vinyl chloride

    H2O

    catalyst

    Ag catalystethylene oxide

    ethylene glycol ethanol

    USES OF LKENES

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    The most popular plastic.

    Uses:

    i) Grocery bags

    ii)Shampoo bottlesiii)Children's toy

    iv)Bullet proof vests

    v)Film wrapping

    vi)Kitchenware

    i) POLYETHENE (PE)

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    ii) POLYVINYL CHLORIDE (PVC)

    C C

    H H

    CIH C C

    H

    H

    CI

    HC

    H

    HC

    CI

    HCH

    H

    C

    CI

    Hnvinyl chloride

    polymerize

    poly(vinyl chloride)PVC, "vinyl"

    USES OF PVC:

    Clothing- PVC fabric has a sheen to it and is waterproof.

    - coats, shoes, jackets, aprons and bags.

    As the insulation on electric wires.

    Producing pipes for various municipal and industrial applications.For examples, for drinking water distribution and wastewater mains.

    As a composite for the production of accessories or housings forportable electronics.

    used in the building industry as a low-maintenance material.

    Ceiling tiles.

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    USE OF ETHANOL: Motor fuel and fuel additive. As a fuel to power Direct-ethanol fuel cells (DEFC) in order to produce

    electricity. As fuel in bipropellant rocket vehicles. In alcoholic beverages.

    An important industrial ingredient and use as a base chemical for otherorganic compounds include ethyl halides, ethyl esters, diethyl ether,acetic acid, ethyl amines and to a lesser extent butadiene.

    Antiseptic use. An antidote.

    Ethanol is easily miscible in water and is a good solvent. Ethanol is less

    polar than water and is used in perfumes, paints and tinctures. Ethanol is also used in design and sketch art markers. Ethanol is also found in certain kinds of deodorants.