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Ethers and Thiols

Ethers

What are they?

How are they used?

What do you know about them?


Structure of Ethers
Similar structure to alcohols

Alcohols: R-OH
OH is hydroxy group

Ethers: R-OR
OR is alkoxy group
Alkoxy group
R groups can be R groups can be
the same: different:

CH3-O-CH3 CH3CH2CH2-O-CH3

Both R groups One R group has


three carbons while
have one carbon
the other has one
Alkoxy group

The root names are used with oxy to


name that portion of the ether:
meth- + -oxy
eth- + -oxy = methoxy
= ethoxy
prop- + -oxy
= propoxy
Naming ethers IUPAC Way
1. Find the root name of the smaller R group
Ex: meth-, eth-, prop-
2. Add oxy
Ex: methoxy, ethoxy, propoxy
3. Add the full name of the larger R group
EXAMPLE:
O
methoxypropane
Name that ether

O O

O
Draw the structure of:
1. methoxypropane

2. methoxyoctane

3. propoxypropane

4. ethoxypentane
Naming Ethers Common
Name
Name by placing the names of the two alkyl
groups attached to the ether oxygen as words
in front of the word ether. Typically this is
done in alphabetical order.

O O
Diethyl Ether Ethyl methyl ether

Butyl propyl ether


O
Properties of ethers

The C-O bond in ethers is polar, making


the molecule polar

Ethers have very low boiling points

Ethers are relatively inert, but flammable


in air
Lets compare
Ether Alcohol
CH3 O-CH2CH3 CH3CH2CH2-OH
Molecular Formula: Molecular Formula:
C3H8O C3H8O
Molecular Weight: Molecular Weight:
60.09g/mol 60.09g/mol
Boiling Point: Boiling Point:
7.9C 97.2C
Preparing ethers
Ethers are formed from alcohols

R-OH + R-OH

R-O-R +H2O
H+

R and R can be the same or


different
Called a dehydration reaction
Predict the products

CH3OH + CH3CH2OH H+

CH3CH2CH2OH + CH3CHCH3 H+

OH
Common uses

Ethers as anesthetics:
Penthrane
Enthrane

Ethers as additives in gasoline


MTBE methyl tert-butyl ether
Thiols
Compounds that contain the sulfhydryl
group (-SH)
Similar to alcohols in structure, but the
sulfur atom replaces the oxygen atom
Have nauseating aromas defense spray
of North American striped skunk
H CH3

Trans-2-butene-1-thiol
H2C H

SH
Naming Thiols
Use the same rules as for alcohols except
that the full name of the alkane is retained.
Add the suffix thiol.
CH3CH2SH ethanethiol
CH3

CH3CHCH2CH2 3-methyl-1-butanethiol
SH

HSCH2CH2SH 1,2-ethanedithiol
Uses of Thiols
Thiols are involved in protein structure and
conformation.
Cysteine is an amino acid that contains a
sulfhydryl group.
BAL (British Anti-Lewisite) is used as an
antidote for mercury poisoning.
Coenzyme A serves as a carrier of acetyl
groups in biochemical reactions.