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  • Hoa-Huu-Co - Phan-Thanh-Son-Nam - Chapter-5-2013-Alkenes - (Cuuduongthancong - Com)

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    1) The document discusses the reactions and properties of alkenes. 2) Alkenes undergo addition reactions such as hydrogenation and halogenation. Reactions follow Markovnikov's rule or anti-Markovnikov regioselectivity. 3) Alkene reactions create geometric isomers and can generate chiral centers, affecting stereochemistry of products.

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    1) The document discusses the reactions and properties of alkenes. 2) Alkenes undergo addition reactions such as hydrogenation and halogenation. Reactions follow Markovnikov's rule or anti-Markovnikov regioselectivity. 3) Alkene reactions create geometric isomers and can generate chiral centers, affecting stereochemistry of products.

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    11 views42 pages

    Hoa-Huu-Co - Phan-Thanh-Son-Nam - Chapter-5-2013-Alkenes - (Cuuduongthancong - Com)

    Uploaded by

    Việt Quốc
    1) The document discusses the reactions and properties of alkenes. 2) Alkenes undergo addition reactions such as hydrogenation and halogenation. Reactions follow Markovnikov's rule or anti-Markovnikov regioselectivity. 3) Alkene reactions create geometric isomers and can generate chiral centers, affecting stereochemistry of products.

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    of 42

    ORGANIC CHEMISTRY

    Dr Nam T. S. Phan
    Faculty of Chemical Engineering
    HCMC University of Technology
    Office: room 211, B2 Building
    Phone: 38647256 ext. 5681
    Email: ptsnam@hcmut.edu.vn
    1

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    Chapter 5: ALKENES
    An sp2
    hybridized
    carbon

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    NOMENCLATURE OF ALKENES
    The IUPAC name of an alkene is obtained by replacing
    the “ane” ending of the corresponding alkane with “ene”

    • Ethylene is an acceptable synonym for ethene in the IUPAC


    system
    • Propylene, isobutylene and other common names ending in
    “ylene” are NOT acceptable IUPAC names
    3

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    Determine the parent
    hydrocarbon – the
    longest continuous
    carbon chain containing
    the C=C

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    Note: Alkenes can have geometric isomers

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    PREPARATION OF ALKENES
    Dehydrations of alcohols
    Acid

    isomerization
    6

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    isomerization 7

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    Eliminations of alkyl halides

    Base

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    Alkyne hydrogenations
    Pd/CaCO3 + Pb(OAc)2 / quinoline

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    REACTIONS OF ALKENES
    Additions of hydrogen halides (AE)

    More stable

    Markovnikov’s rule 10

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    Carbocation rearrangement

    More stable

    11

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    12
    More stable
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    Stereochemistry

    Racemic mixture 13

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    Already has 1 asymmetric carbon

    14

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    2 asymmetric carbons are created

    15

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    Additions of hydrogen bromide (AR)

    Electrophilic addition (AE)

    Radical addition (AR) – only for HBr 16

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    Reaction
    mechanism:

    17

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    Additions of halogens

    18

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    Major
    addition
    product –
    NOT a
    dihalide

    19

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    Stereochemistry

    20

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    21

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    Stereochemistry
    2 asymmetric carbons are created

    Trans-2-butene Æ meso compound 22

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    Additions of water – hydration reactions
    Water is too weakly acidic to allow the hydrogen to act
    as an electrophile

    Markovnikov’s rule

    H2SO4, H3PO4…
    23

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    Reaction
    mechanism:

    Carbocation
    rearrangement
    might occur

    24

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    Alcohols by oxymercuration-reduction

    Markovnikov’s rule

    No carbocation formation, no rearrangement

    25

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    Additions of borane: hydroboration-oxidation

    26

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    Regioselectivity:

    Anti-Markovnikov

    27

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    Additions of hydrogen – hydrogenation

    28

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    Reaction mechanism:

    Syn addition

    29

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    Stereochemistry

    30

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    31

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    Alkene epoxidations – Anti hydroxylations

    32

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    Stereochemistry

    33

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    Reactions of epoxides

    34

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    35

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    Stereochemistry Anti additions

    36

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    Syn hydroxylations of alkenes

    37

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    Reaction mechanism: Syn additions

    38

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    Permanganate cleavage of alkenes

    39

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    Ozonolysis of alkenes

    40

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    In the presence of an oxidizing agent, the products
    will be ketones / carboxylic acids
    41

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    Polymerizations

    42

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