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    Oxidationalkene

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    Nur Aiman Nor Din
    1) Alkenes can be oxidized by dilute cold KMnO4 or hot concentrated KMnO4. Dilute cold KMnO4 adds OH groups across the double bond, while hot concentrated KMnO4 cleaves the double bond, forming carbonyl products like ketones or carboxylic acids. 2) Ozonolysis of alkenes forms unstable ozonides that decompose to carbonyl compounds like aldehydes and ketones upon reduction. This allows the location of double bonds in unknown alkenes to be determined. 3) Acid-catalyzed dehydration of neopentyl alcohol produces 2-methyl-2-butene as the major product

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    Oxidationalkene

    Uploaded by

    Nur Aiman Nor Din
    614 views23 pages
    1) Alkenes can be oxidized by dilute cold KMnO4 or hot concentrated KMnO4. Dilute cold KMnO4 adds OH groups across the double bond, while hot concentrated KMnO4 cleaves the double bond, forming carbonyl products like ketones or carboxylic acids. 2) Ozonolysis of alkenes forms unstable ozonides that decompose to carbonyl compounds like aldehydes and ketones upon reduction. This allows the location of double bonds in unknown alkenes to be determined. 3) Acid-catalyzed dehydration of neopentyl alcohol produces 2-methyl-2-butene as the major product

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    1) Alkenes can be oxidized by dilute cold KMnO4 or hot concentrated KMnO4. Dilute cold KMnO4 adds OH groups across the double bond, while hot concentrated KMnO4 cleaves the double bond, forming carbonyl products like ketones or carboxylic acids. 2) Ozonolysis of alkenes forms unstable ozonides that decompose to carbonyl compounds like aldehydes and ketones upon reduction. This allows the location of double bonds in unknown alkenes to be determined. 3) Acid-catalyzed dehydration of neopentyl alcohol produces 2-methyl-2-butene as the major product

    Copyright:

    Attribution Non-Commercial (BY-NC)
    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    614 views23 pages

    Oxidationalkene

    Uploaded by

    Nur Aiman Nor Din
    1) Alkenes can be oxidized by dilute cold KMnO4 or hot concentrated KMnO4. Dilute cold KMnO4 adds OH groups across the double bond, while hot concentrated KMnO4 cleaves the double bond, forming carbonyl products like ketones or carboxylic acids. 2) Ozonolysis of alkenes forms unstable ozonides that decompose to carbonyl compounds like aldehydes and ketones upon reduction. This allows the location of double bonds in unknown alkenes to be determined. 3) Acid-catalyzed dehydration of neopentyl alcohol produces 2-methyl-2-butene as the major product

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    Download as PPT, PDF, TXT or read online from Scribd
    Download as ppt, pdf, or txt
    of 23

    6 ) Oxidation of Alkenes

    Alkenes undergo a number of reactions in which the C=C is oxidized

    KMnO4
    basic,cold,dilute acidic,hot,concentrated

    ozonolysis

    VIDEO1

    i)

    Reaction of alkenes with dilute, cold KMnO4, Baeyers test


    The reaction known as hydroxylation. It involves the addition of the two OH groups to the double bond Potassium permanganate in alkaline solution can be used to oxidise alkenes to 1,2-diols (glycols). This test is used to distinguish alkenes.

    Unsaturated hydrocarbon

    KMnO4 (purple)

    dilute, cold

    C C OH OH

    MnO2 (brown precipitate)

    Observation: Purple colour of KMnO4 decolourised and brown precipitate formed.

    Saturated hydrocarbon
    dilute, cold

    CH3CH2CH3 + KMnO4

    No reaction

    Observation: the purple color of KMnO4 remains

    y This reaction is called Baeyers test. test y It is a test for the presence of C=C where the purple colour of the KMnO4 decolourised, and brown precipitate of MnO2 is formed.

    Example:
    H2 C CH2

    +
    H

    KMnO4 H C H C

    OH ,H2 O cold

    MnO2

    OH OH

    ii) Reactions of alkenes with hot, concentrated KMnO4


    When oxidation of the alkene is carried out in acidic solution of KMnO4, cleavage of the double bond occurs and carbonyl-containing products are obtained.

    If the double bond is tetrasubstituted the tetrasubstituted, two carbonyl-containing products are ketones
    CH3 H3C C C CH3 O H3C C CH3 CH3
    H+, ( (i) OH ,heat
    -

    KMnO4

    (ii) H3O

    H 3C

    CH3

    If a hydrogen is present at double bond, bond one of the carbonyl-containing products is a carboxylic acid acid; If two hydrogens are present on one carbon, carbon CO2 is formed.

    2)

    H2C

    CH CH3

    +
    O C

    KMnO4

    H+, ( (i) OH ,heat

    (ii) H3O

    HO

    CH3

    CO2

    H2 O

    The oxidative cleavage of alkenes can be used to establish the location of the double bond in an unknown alkene.

    Example: An unknown alkene with the formula C7H14 undergoes oxidation with hot acidic potasium permanganate solution to form propanoic acid and butanoic acid. What is acid. the structure of this alkene?

    C 7 H14

    +
    O

    KMnO4

    H+, ( (i) OH-,heat

    (ii) H3 O

    O OH

    H3 C

    CH2

    CH2 C H3 C CH2 OH

    Answer:
    O H3C CH2 C OH O CH2 C CH2 OH H3C butanoic acid

    propanoic acid

    H H H3C CH2C C CH2CH2CH3 3-heptene

    Example
    An unknown alkene undergoes oxidation in hot acidic KMnO4 to give the following product: O O OH

    CH3CCH2CH2CH2CH2C

    Deduce the structural formula for the unknown alkene.

    iii) Ozonolysis of Alkenes


    y A more widely used method for locating the double bond of an alkene is the use of ozone (O3). Ozone reacts vigorously with alkenes to form unstable compounds called molozonides, molozonides which rearrange spontaneously to form compounds called ozonides. ozonides.
    VIDEO2

    C O O

    O3

    ozonide

    y Ozonides: y very unstable compounds y can easily explode violently y they are not usually isolated but are reduced directly by treatment with water and in the presence of zinc and acid (normally acetic acid) to give carbonyl compounds (either aldehydes or ketones).

    O C O O C

    +
    R

    Zn

    H2 O,H

    ozonide
    H

    C=O

    O=C
    R

    Example:
    CH3 H3C C CH CH3 CH3 H3C C O (i) O3 (ii) Zn,H2O/H
    +

    CH3

    Exercise
    1. Write the structure of alkene that would produce the following products when treated with ozone followed by water, zinc and acid CH3COCH3 and CH3CH(CH3)CHO

    Example
    Deduce the structural formula of an alkene that gives the following compound when it reacts with ozone in the presence of Zn / H+. O=CH-CH2-CH2-CH(CH3)CH=O

    2. Acid-catalyzed dehydration of neopentyl alcohol, (CH3)3CCH2OH, yields 2-methyl-2-butene as the major product. Outline a mechanism showing all steps in its formation.

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