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    EthersThiols and Thioesters

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    PRINCESS NOELLEE TRAYVILLA
    1. Ethers have the general formula R-O-R and can be symmetrical or asymmetrical. They are named based on the alkyl groups attached to the oxygen, in alphabetical order. 2. Thiols are sulfur analogues of alcohols with the general formula R-SH. They have unpleasant odors and are named similarly to alcohols but with the suffix changed to "thiol". 3. Thioethers have the formula R-S-R and are similar to ethers but contain sulfur instead of oxygen. They are named by identifying the parent chain and substituents according to IUPAC nomenclature rules.

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    EthersThiols and Thioesters

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    PRINCESS NOELLEE TRAYVILLA
    48 views24 pages
    1. Ethers have the general formula R-O-R and can be symmetrical or asymmetrical. They are named based on the alkyl groups attached to the oxygen, in alphabetical order. 2. Thiols are sulfur analogues of alcohols with the general formula R-SH. They have unpleasant odors and are named similarly to alcohols but with the suffix changed to "thiol". 3. Thioethers have the formula R-S-R and are similar to ethers but contain sulfur instead of oxygen. They are named by identifying the parent chain and substituents according to IUPAC nomenclature rules.

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    EthersThiols and Thioesters

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    1. Ethers have the general formula R-O-R and can be symmetrical or asymmetrical. They are named based on the alkyl groups attached to the oxygen, in alphabetical order. 2. Thiols are sulfur analogues of alcohols with the general formula R-SH. They have unpleasant odors and are named similarly to alcohols but with the suffix changed to "thiol". 3. Thioethers have the formula R-S-R and are similar to ethers but contain sulfur instead of oxygen. They are named by identifying the parent chain and substituents according to IUPAC nomenclature rules.

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    © All Rights Reserved
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    48 views24 pages

    EthersThiols and Thioesters

    Uploaded by

    PRINCESS NOELLEE TRAYVILLA
    1. Ethers have the general formula R-O-R and can be symmetrical or asymmetrical. They are named based on the alkyl groups attached to the oxygen, in alphabetical order. 2. Thiols are sulfur analogues of alcohols with the general formula R-SH. They have unpleasant odors and are named similarly to alcohols but with the suffix changed to "thiol". 3. Thioethers have the formula R-S-R and are similar to ethers but contain sulfur instead of oxygen. They are named by identifying the parent chain and substituents according to IUPAC nomenclature rules.

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    Ethers, Thiols and

    Thioesters
    POC LEC (GROUP 1) BSPh-1A
    ETHERS
    • Ethers can be defined as a class or a group of organic compounds
    comprising an oxygen atom, which is bonded to two same or different
    alkyl or aryl groups.

    • The general formula for ether is R-O-R, where R represents an alkyl


    group.
    ETHERS
    • Ethers can be generally classified into two categories, based on their
    attached substituent groups.
    1. Symmetrical ethers – Two identical groups attached to either side of an
    oxygen atom.
    2. Asymmetrical ethers – Two different groups attached to either side of an
    oxygen atom.
    ETHERS

    Physical Properties Chemical Properties


    • Molecules only slightly polar
    • No hydrogen on the oxygen atoms to form
    hydrogen bonds – only weak forces of
    attraction between molecules.
    • Boiling points similar to corresponding alkane.
    • Lower ethers, very volatile, highly flammable.
    • Only slightly soluble in water, mix well with
    non-polar solvents eg. Alkanes (Like dissolves
    like).
    IUPAC Nomenclature
    • Ethers are named simply by the names of two alkyl/aryl groups bonded to oxygen and add the word
    ‘ether’. Those alkyl groups are listed in alphabetical order.
    • For example, t-butyl methyl ether, ethyl methyl ether.
    • If only one alkyl/aryl group is shown in the name of a particular ether, it implies two identical groups, as
    in ethyl ether for diethyl ether. Naming for ethers adopted by IUPAC uses a more complex group as the
    root name, with the oxygen atom and the smaller group named as an alkoxy substituent. Thus, in IUPAC
    systems, ethers are alkoxy alkanes.
    • Example: ethoxyethane (diethyl ether), methoxy ethane (methyl ethyl ether), 2-methoxy-2-
    methylpropane (methyl tert-butyl ether), phenoxy benzene (diphenyl ether).This IUPAC nomenclature is
    very useful for naming compounds with additional functional groups because these functional groups
    can be described by the root name.
    Rules for Naming the Ether Using IUPAC
    Nomenclature
    • Rule 1: Select the longest carbon chain as the base chain and give the
    base name.

    • Rule 2: Change the name of the other hydrocarbon group ends with ‘yl’
    change into ‘oxy’.
    Example: Methyl becomes methoxy and ethyl becomes an ethoxy group.
    Rules for Naming the Ether Using IUPAC
    Nomenclature
    • Rule 3: Alkoxy name is placed with a locator number in front of the base chain name.
    Example:
    1. CH3 – O – CH2 – CH2 – CH2 – CH3    (1 – Methoxybutane)
    2. CH3 – CH (CH3) – CH2 – O – CH2 – CH3  ( 1- Ethoxy – 2- methylpropane)

    • Rule 4: Change the name of the other hydrocarbon group ends with ‘yl’ change into ‘oxy’.
    Example: Methyl becomes methoxy and ethyl becomes an ethoxy group.
    THIOLS
    • Thiols can be defined as a sulfur analogue of alcohols. In a simpler way, it
    is an organic compound consisting of compounds with a sulfur atom. It is
    also referred to as mercaptan.

    • The general formula for thiol is R-SH, where -SH represents sulfhydryl


    group.
    THIOLS
    Physical Properties Chemical Properties

    • They have unpleasant odors


    • They are nonpolar compounds
    • Low boiling points
    • Almost insoluble in water
    IUPAC Nomenclature
    • Thiols are sulfur analogues of alcohols, containing an SH group in place
    of the OH group. When naming a thiol, we follow the same rules we
    discussed earlier for the IUPAC nomenclature rules for alcohols with the
    focus on giving the carbon bonded to the SH group the lowest locant.
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    • Rule 1: Identify the parent chain.

    • Rule 2: Identify the substituents.

    • Rule 3: Number the parent chain giving the carbon bonded to the SH group the lowest
    locant.

    • Rule 4: Put everything together having the substituents in alphabetical order.


    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    • The presence of the SH group is identified by changing the parent suffix
    from “e” to “thiol”:
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    • For simple thiols, the common name can be derived by naming the alkyl
    group connected to the SH and adding the word mercaptan:
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    • If it is a branched molecule, choose the parent chain such that it is the longest carbon chain
    containing the carbon atom connected to the SH group:
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    • The SH group has a higher priority than alkyl substituents or π bonds. Therefore, you need to number the
    parent chain such that the SH gets the lowest possible number:
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    • When naming a cyclic thiol, start numbering the ring beginning with the carbon connected to the SH group.
    This rule always puts the SH group at C1, therefore, the “1” is usually omitted from the name:
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    Rules for Naming the Thiol Using IUPAC
    Nomenclature
    THIOETHERS

    • A thioether is similar to an ether except that it contains a sulfur atom in


    place of the oxygen.

    • The general formula for thioester is R-S-R.


    THIOETHERS

    Physical Properties Chemical Properties


    • Molecules only slightly polar
    • No hydrogen on the oxygen atoms to form
    hydrogen bonds – only weak forces of
    attraction between molecules.
    • Boiling points similar to corresponding alkane.
    • Less volatile, higher melting, and less
    hydrophilic.
    • Only slightly soluble in water, mix well with
    non-polar solvents eg. Alkanes (Like dissolves
    like).
    Rules for Naming the Thioethers Using
    IUPAC Nomenclature
    Rules for Naming the Thioethers Using
    IUPAC Nomenclature
    Common Nomenclature of Ethers, Thiol
    and Thioethers
    Common Nomenclature of Ethers, Thiol
    and Thioethers

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