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