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    Alcohol Ether Epoxide

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    ANISTHESIAHYUNI BINTI DURMAN FKJ
    1) Alcohols, ethers, and epoxides contain carbon-oxygen bonds and are classified based on functional groups. 2) Alcohols contain hydroxyl groups, ethers have two alkyl groups bonded to an oxygen, and epoxides form three-membered rings. 3) These compounds can be synthesized through reactions such as nucleophilic substitution, hydration of alkenes, reduction of carbonyls, and epoxidation of alkenes.

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    Alcohol Ether Epoxide

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    ANISTHESIAHYUNI BINTI DURMAN FKJ
    41 views31 pages
    1) Alcohols, ethers, and epoxides contain carbon-oxygen bonds and are classified based on functional groups. 2) Alcohols contain hydroxyl groups, ethers have two alkyl groups bonded to an oxygen, and epoxides form three-membered rings. 3) These compounds can be synthesized through reactions such as nucleophilic substitution, hydration of alkenes, reduction of carbonyls, and epoxidation of alkenes.

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    ALCOHOL ETHER EPOXIDE

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    1) Alcohols, ethers, and epoxides contain carbon-oxygen bonds and are classified based on functional groups. 2) Alcohols contain hydroxyl groups, ethers have two alkyl groups bonded to an oxygen, and epoxides form three-membered rings. 3) These compounds can be synthesized through reactions such as nucleophilic substitution, hydration of alkenes, reduction of carbonyls, and epoxidation of alkenes.

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    © All Rights Reserved
    Download as PDF, TXT or read online from Scribd
    Download as pdf or txt
    41 views31 pages

    Alcohol Ether Epoxide

    Uploaded by

    ANISTHESIAHYUNI BINTI DURMAN FKJ
    1) Alcohols, ethers, and epoxides contain carbon-oxygen bonds and are classified based on functional groups. 2) Alcohols contain hydroxyl groups, ethers have two alkyl groups bonded to an oxygen, and epoxides form three-membered rings. 3) These compounds can be synthesized through reactions such as nucleophilic substitution, hydration of alkenes, reduction of carbonyls, and epoxidation of alkenes.

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    of 31

    CHAPTER 2

    ALCOHOL, ETHER & EPOXIDES


    Introduction
     Alcohol, ether and epoxides are three functional
    groups that contain carbon-oxygen  bonds.
     Alcohols contain hyroxy (OH) group and classified as
    primary, secondary, or tertiary.
     Ethers have two alkyl groups bonded to an oxygen
    atom.
     Epoxides are ethers having the oxygen atom in a
    three-membered ring. Also called as oxiranes.
    Naming alcohol
     Find the longest carbon chain containing the
    carbon with the -OH group.
     Drop the -e from the alkane name, add -ol.
     Number the chain, starting from the end
    closest to the -OH group.
     Number and name all substituents.
    Naming Ether
     Simple ether are usually assigned common
    names
     Example: CH3
    CH3 O C CH3
    CH3CH2 O CH2CH3
    CH3
    diethyl ether or
    t-butyl methyl ether or
    ethyl ether
    methyl t-butyl ether
     More complex ethers are named using
    IUPAC system: Alkoxy alkane
    IUPAC System
     Examples:

    CH3 O CH3
    CH3 O C CH3
    CH3
    2-methyl-2-methoxypropane Methoxycyclohexane
    Naming Epoxides

    • Alkene oxide, from usual synthesis method


    H
    peroxybenzoic acid
    O cyclohexene oxide
    H

    • Epoxy attachment to parent compound,


    1,2-epoxy-cyclohexane
    • Oxirane as parent, oxygen number 1
    O
    H CH3
    trans-2-ethyl-3-methyloxirane
    CH3CH2 H
    Physical Properties
     Alcohol usually high boiling points due to
    hydrogen bonding between molecules.
     Small alcohols are miscible in water, but
    solubility decreases as the size of the alkyl
    group increases.
     Boiling point of ether is less than alcohol
    Preparation of Alcohol, Ethers, and
    Epoxides
     Alcohol and ethers are both common
    products of nucleophilic substitution.
     Highest yields of products are obtained with
    unhindered methyl and 1o alkyl halides
     A hydroxide nucleophile is needed to
    synthesize alcohol
     An alkoxide ion + 1 alkyl bromide to
    synthesize ether
    Syntheses of Alcohol by grignard
    reagent
     Grignard (R-Mg-X) + formaldehyde yields a
    primary alcohol with one additional carbon.
     Grignard + aldehyde yields a secondary
    alcohol.
     Grignard + ketone yields a tertiary alcohol.
    Syntheses of Alcohol by Reduction of
    Carbonyl
     Reduction of aldehyde yields 1º alcohol.
     Reduction of ketone yields 2º alcohol.
     Reagents:
     Sodium borohydride, NaBH4 (Only reacts with
    carbonyl of aldehyde or ketone)
     Lithium aluminum hydride, LiAlH4 (Converts esters
    and acids to 1º alcohols)
     Raney nickel (reacts with carbonyl of aldehyde or
    ketone to produce 1o and 2o alcohol respectively)
    Syntheses of Alcohol from Alkene
     Dehydration of alkene
     Hydroboration-oxidation of alkene
     Hydroxilation
    Hydration of Alkenes

    + H OH
    H
    C C + H2O C C
    alkene
    alcohol

     Reverse of dehydration of alcohol


     Use very dilute solutions of H2SO4 or H3PO4
    to drive equilibrium toward hydration.
    hydroboration
    hydroxylation
    Preparation of Ether
     Alkoxide ion + 1 alkyl bromide (Williamson
    Synthesis)
     Use mercuric acetate with an alcohol to add
    RO-H to a double bond and form the
    Markovnikov product.
    Synthesis of Epoxides
     Peroxyacid epoxidation

    • Cyclization of Halohydrin
    _ _ O
    HO H OH O H
    H2O, Cl2
    H H Cl Cl H H
    H H
    =>
    Reactions of Alcohol
    Dehydration Reactions

     Conc. H2SO4 produces alkene


     Carbocation intermediate
     Zaitsev product
     Bimolecular dehydration produces ether
     Low temp, 140°C and below, favors ether
     High temp, 180°C and above, favors alkene
    Dehydration Mechanisms
    H
    OH OH
    H2SO4
    CH3CHCH3 CH3CHCH3
    CH3CHCH3
    alcohol
    H2O
    CH2 CHCH3
    +
    H3O
    CH3OH CH3 OH2 CH3 O CH3
    H
    CH3OH CH3OCH3
    H2O
    Conversion of Alcohol to Alkyl
    Halides
     -OH of alcohol is protonated
     -OH2+ is good leaving group
     3° and 2° alcohols react with Br- via SN1
     1° alcohols react via SN2

    + H -
    H3O Br
    R O H R O H R Br =>
    Conversion of Alcohol to R-X with
    SOCl2 and PBr3
     Treatment of 1o and 2o alcohol with thionyl
    chloride (SOCl2) and pyridine forms an alkyl
    chloride.
     Treatment with (PBr3) forms an alkyl bromide
    Reaction of Ethers with Strong Acid
     Ethers react with HBr or HI, both C-O bonds are
    cleaved and two alkyl halides are formed as product
     Mechanism

    H
    + _
    CH3 O CH3 H Br CH3 O CH3
    _

    + Br

    H
    _ +
    Br CH3 O CH3 Br CH3 + H O CH3

    • Alcohol is protonated, halide attacks, and


    another molecule of alkyl bromide is formed.
    Reactions of Epoxides with
    Nucleophiles
     Trans diol formed in water solvent.
    +
    O H , H2O HO H

    H H H OH

    • Alkoxy alcohol formed in alcohol solvent.


    +
    O H , CH3OH HO H

    H H H OCH3

    • 1,2-Dihalide formed with HI or HBr. =>


    Reactions of Epoxides with Base
     With aqueous hydroxide, a trans 1,2-diol is
    formed.
     With alkoxide in alcohol, a trans 1,2-alkoxy
    alcohol is formed.
     These are the same products that were formed
    in acid.
     Different products are formed in acid and base if
    epoxide is unsymmetrical.
    Orientation of
    Epoxide Opening
     Base attacks the least_ hindered carbon.
    O O OH
    CH3CH2OH
    HC CH2 HC CH2 HC CH2
    CH3 OCH2CH3 CH3 OCH2CH3 CH3 OCH2CH3

    • In acid, the nucleophile attacks the protonated


    epoxide at the most substituted carbon.
    H H3C OH H3C OH
    O+ HC CH2 HC CH2
    HC CH2 OCH2CH3
    H OCH
    +
    2CH3
    CH3
    CH3CH2OH

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