Scribd Logo
Upload

Welcome to Scribd!

  • 20 views

    Swern Oxidation

    Uploaded by

    28 Che MOTHILAL G

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd

    Swern Oxidation

    Uploaded by

    28 Che MOTHILAL G
    20 views13 pages

    Original Title

    Swern oxidation

    Copyright

    © © All Rights Reserved

    Available Formats

    PPTX, PDF, TXT or read online from Scribd

    Did you find this document useful?

    Is this content inappropriate?

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    20 views13 pages

    Swern Oxidation

    Uploaded by

    28 Che MOTHILAL G

    Copyright:

    © All Rights Reserved
    Download as PPTX, PDF, TXT or read online from Scribd
    Download as pptx, pdf, or txt
    You are on page 1of 13

    Anna university,

    ceg campus,
    department of chemistry.

    Topic
    Swern oxidation
    By
    V Sai Ram
    • It is a chemical reaction whereby a primary or secondary alcohol
    (−OH) is oxidized to an aldehyde (−CH=O) or ketone (>C=O)
    • It is important to note that these aldehydes do not undergo further
    reaction to produce carboxylic acids
    • Using oxalyl chloride, dimethyl sulfoxide (DMSO) and an organic base,
    such as triethylamine
    • It is one of the many oxidation reactions commonly referred to as
    'activated DMSO' oxidations. The reaction is known for its mild
    character and wide tolerance of functional groups.
    Oxalyl chloride
    • Oxalyl chloride was first prepared in 1892 by the French chemist
    Adrien Fauconnier, who reacted diethyl oxalate with phosphorus
    pentachloride. It can also be prepared by treating oxalic acid with
    pentachloride phosphorus
    • Oxalyl chloride is produced commercially from ethylene carbonate.
    Photochlorination gives the perchloroethylene
    carbonate C2Cl4O2CO and hydrogen chloride HCl, which is subsequently
    degraded to oxalyl chloride and phosgene COCl2
    • Preparation
    C2H4O2CO + 4 Cl2 → C2Cl4O2CO + 4 HCl
    C2Cl4O2CO → C2O2Cl2 + COCl2
    Applications in organic synthesis
    • Oxidation of alcohols
    • Addition of a primary or secondary alcohol to a solution of oxalyl
    chloride in DMSO, followed by quenching with an organic base such
    as triethylamine converts alcohols to the
    corresponding aldehydes and ketones via the process known as
    the Swern oxidation.
    Mechanism
    The first step of the Swern oxidation is the low
    temperature reaction of DMSO, 1a, formally as
    resonance contributor 1b, with oxalyl chloride, 2. The
    first intermediate, 3, quickly decomposes giving off
    carbon dioxide and carbon monoxide and producing
    chloro(dimethyl)sulfonium chloride, 4.
    After addition of the alcohol 5, the chloro(dimethyl)sulfonium chloride 4
    reacts with the alcohol to give the key alkoxysulfonium ion intermediate,
    6. The addition of at least 2 equivalents of base — typically triethylamine
    — will deprotonate the alkoxysulfonium ion to give the sulfur ylide 7. In
    a five membered ring transition state, the sulfur ylide 7 decomposes to
    give dimethyl sulfide and the desired carbonyl compound 8.
    Applications of swern oxidation
    • The applications of Swern oxidation are as follows:
    • When turning secondary alcohols into aldehydes, the Swern oxidation
    is extremely helpful.
    • The byproducts of the reaction are low boiling and simple to remove,
    it is used to produce aldehydes on a big scale.
    Advantages & Disadvantages of Swern
    oxidation

    • Advantages
    • Swern oxidation Advantages are given below:
    • Alcohols can be oxidized using the Swern method without the use of harmful metals.
    • At extremely low temperatures, this reaction frequently happens without any problems.
    • This typically results in highly selective methods that typically don’t damage other functional
    groups of complicated molecules.
    • Disadvantages
    • Swern oxidation disadvantages are given below:
    • Dimethyl sulphide, a side product of this process that has a foul smell that can get very
    offensive, is a drawback.

    You might also like