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    Ethers and Thioethers

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    alomical
    1. Ethers and thioethers are named using IUPAC nomenclature by listing the groups attached to oxygen or sulfur in alphabetical order, with "ether" or "sulfide" as the last word. 2. Ethers and thioethers can be prepared through nucleophilic substitution reactions and resemble alkanes more than alcohols in terms of boiling point due to an inability to form hydrogen bonds. 3. Ethers and thioethers can oxidize to form sulfoxides and sulfones, respectively, and thioethers can act as nucleophiles in reactions forming sulfonium salts.

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    Ethers and Thioethers

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    alomical
    66 views16 pages
    1. Ethers and thioethers are named using IUPAC nomenclature by listing the groups attached to oxygen or sulfur in alphabetical order, with "ether" or "sulfide" as the last word. 2. Ethers and thioethers can be prepared through nucleophilic substitution reactions and resemble alkanes more than alcohols in terms of boiling point due to an inability to form hydrogen bonds. 3. Ethers and thioethers can oxidize to form sulfoxides and sulfones, respectively, and thioethers can act as nucleophiles in reactions forming sulfonium salts.

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    lecture notes

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    1. Ethers and thioethers are named using IUPAC nomenclature by listing the groups attached to oxygen or sulfur in alphabetical order, with "ether" or "sulfide" as the last word. 2. Ethers and thioethers can be prepared through nucleophilic substitution reactions and resemble alkanes more than alcohols in terms of boiling point due to an inability to form hydrogen bonds. 3. Ethers and thioethers can oxidize to form sulfoxides and sulfones, respectively, and thioethers can act as nucleophiles in reactions forming sulfonium salts.

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    66 views16 pages

    Ethers and Thioethers

    Uploaded by

    alomical
    1. Ethers and thioethers are named using IUPAC nomenclature by listing the groups attached to oxygen or sulfur in alphabetical order, with "ether" or "sulfide" as the last word. 2. Ethers and thioethers can be prepared through nucleophilic substitution reactions and resemble alkanes more than alcohols in terms of boiling point due to an inability to form hydrogen bonds. 3. Ethers and thioethers can oxidize to form sulfoxides and sulfones, respectively, and thioethers can act as nucleophiles in reactions forming sulfonium salts.

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    of 16

    Ethers and Thioethers

    Bond
    Bondangles
    anglesat
    atoxygen
    oxygenare
    aresensitive
    sensitive
    to
    tosteric
    stericeffects
    effects
    O

    O
    H

    CH3

    105

    O
    CH3
    112

    H
    108.5

    O
    CH3

    C(CH3)3

    (CH3)3C
    132

    Functional
    FunctionalClass
    ClassIUPAC
    IUPACNames
    Namesof
    ofEthers
    Ethers
    name the groups attached to oxygen in
    alphabetical order as separate words; "ether" is
    last word
    CH3OCH2 CH3
    ethyl methyl ether

    CH3CH2OCH2CH2CH2Cl
    3-chloropropyl ethyl ether

    CH3CH2OCH2 CH3
    diethyl ether

    Substitutive
    SubstitutiveIUPAC
    IUPACNames
    Namesof
    ofEthers
    Ethers
    name as alkoxy derivatives of alkanes
    CH3OCH2 CH3
    methoxyethane

    CH3CH2OCH2 CH3
    ethoxyethane

    CH3CH2OCH2CH2CH2Cl
    1-chloro-3-ethoxypropane

    An
    Anoxygen
    oxygenatom
    atomaffects
    affectsgeometry
    geometryin
    inmuch
    muchthe
    the
    same
    sameway
    wayas
    asaaCH
    CH22group
    group

    most stable conformation of diethyl ether


    resembles pentane

    An
    Anoxygen
    oxygenatom
    atomaffects
    affectsgeometry
    geometryin
    inmuch
    muchthe
    the
    same
    sameway
    wayas
    asaaCH
    CH22group
    group

    most stable conformation of tetrahydropyran


    resembles cyclohexane

    PREPARATION
    PREPARATION

    CH3CH2CH2CH2ONa + CH3CH2I

    CH3CH2CH2CH2OCH2CH3 + NaI
    (71%)

    Ethers
    Ethersresemble
    resemblealkanes
    alkanesmore
    morethan
    thanalcohols
    alcohols
    with
    withrespect
    respectto
    toboiling
    boilingpoint
    point
    boiling point
    36C
    O

    35C

    OH 117C

    Intermolecular hydrogen
    bonding possible in
    alcohols; not possible
    in alkanes or ethers.

    Ethers
    Ethersresemble
    resemblealcohols
    alcoholsmore
    morethan
    thanalkanes
    alkanes
    with
    withrespect
    respectto
    tosolubility
    solubilityin
    inwater
    water
    solubility in water (g/100 mL)
    very small
    7.5

    OH

    Hydrogen bonding to
    water possible for ethers
    and alcohols; not
    possible for alkanes.

    Summary
    Summaryof
    ofreactions
    reactionsof
    ofethers
    ethers

    . Ethers are relatively unreactive.


    Their low level of reactivity is one reason why
    ethers are often used as solvents in chemical
    reactions.
    Ethers oxidize in air to form explosive
    hydroperoxides and peroxides.

    REACTIONS
    REACTIONS

    CH3CHCH2CH3
    OCH3

    HBr
    heat

    CH3CHCH2CH3 + CH3Br
    Br

    H
    H
    (81%)
    H

    CH3OCH3

    H+

    CH3O+CH3
    H

    Substitutive
    SubstitutiveIUPAC
    IUPACNames
    Namesof
    ofSulfides
    Sulfides
    name as alkylthio derivatives of alkanes
    CH3SCH2 CH3
    methylthioethane

    SCH3
    (methylthio)cyclopentane

    CH3CH2SCH2 CH3
    ethylthioethane

    Functional
    FunctionalClass
    ClassIUPAC
    IUPACNames
    Namesof
    ofSulfides
    Sulfides
    analogous to ethers, but replace ether as last
    word in the name by sulfide.
    CH3SCH2 CH3
    ethyl methyl sulfide
    CH3CH2SCH2 CH3
    diethyl sulfide

    SCH3
    cyclopentyl methyl sulfide

    Preparation
    Preparationof
    ofRSR'
    RSR'

    prepared by nucleophilic substitution (SN2)

    CH3CHCH
    Cl

    CH2

    R'

    NaSCH3
    methanol

    R'

    CH3CHCH
    SCH3

    CH2

    sulfide

    R'

    Oxidation
    Oxidationof
    ofRSR'
    RSR'

    O
    +
    R S R'

    sulfoxide

    O
    R

    ++
    S R'
    O

    sulfone

    either the sulfoxide or the sulfone can be isolated


    depending on the oxidizing agent and reaction
    conditions

    Sulfides
    Sulfidescan
    canact
    actas
    asnucleophiles
    nucleophiles

    S
    R'

    R"

    S
    R'

    product is a sulfonium salt

    R"

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