LOGO
Lecture 6:
ORGANIC COMPOUNDS THAT CONTAIN OXYGEN,
HALOGEN, OR SULFUR
Organic Chemistry – FALL 2015
Course lecturer :
Jasmin Šutković
16th November 2015
CHAPTER OUTLINE
Book chapter 14
14.1 Introduction
14.2 Structure and Properties of Alcohols
14.3 Nomenclature of Alcohols
14.4 Interesting Alcohols
14.5 Reactions of Alcohols
14.6 FOCUS ON HEALTH & MEDICINE:
Ethanol, the Most Widely
Abused Drug
14.7 Structure and Properties of Ethers
14.8 FOCUS ON HEALTH & MEDICINE:
Ethers as Anesthetics
14.9 Alkyl Halides
14.10 Organic Compounds That
Contain Sulfur
International University of Sarajevo
Introduction
 CHAPTER 14 concentrates on four families of organic
compounds that contain a carbon singly bonded to a
heteroatom—alcohols (ROH), ethers (ROR), alkyl
halides (RX, X = F, Cl, Br, or I), and thiols (RSH).
 Alcohols are the most widely occurring
 Ethers are the most common anesthetics in use
today
 Alkyl halides, widely used as industrial solvents
and refrigerants
 The –SH group of thiols plays an important role
in protein chemistry.
Alcohols can be prepared from, and converted into, many other kinds
of compounds.
Alcohols, ethers, alkyl halides, and thiols are four families of compounds
that contain a carbon atom singly bonded to a heteroatom—oxygen,
halogen, or sulfur
Structure of Alcohols
Alcohols contain a hydroxyl group (OH group) bonded to
a tetrahedral carbon atom.
Alcohols are classifi ed as primary (1°), secondary (2°), or
tertiary (3°) based on the number of carbon
atoms bonded to the carbon with the OH group
Common features
Because oxygen is much more electronegative than carbon or hydrogen,
the CO and OH bonds are polar. Since an alcohol contains two polar
bonds and a bent shape, it has a net dipole.
Alcohols are also capable of intermolecular hydrogen bonding,
since they possess a hydrogen atom bonded to an oxygen.
Nomenclature
 In the IUPAC system, alcohols are identifi ed by the suffi x -ol
Reaction of Alcohols
 The most general method for preparing
alcohols, both in the laboratory and in
living organisms, is by the reduction of a
carbonyl compound.
Reaction of Alcohols
Alcohols also undergo —dehydration and
oxidation.
DEHYDRATION
When an alcohol is treated with a strong acid such as
H2SO4, the elements of water are lost and an alkene is
formed as product. Loss of H2O from a starting material
is called dehydration.
Oxidation
 Perhaps the most valuable reaction of alcohols is
their oxidation to give carbonyl compounds—the
opposite of the reduction of carbonyl compounds
to give alcohols.
 Primary alcohols yield aldehydes or carboxylic
acids,
 Secondary alcohols yield ketones,
 Tertiary alcohols don’t normally react with
most oxidizing agents
Oxidation
 Recall section 12.8
FOCUS ON THE HUMAN BODY
OXIDATION AND BLOOD ALCOHOL
SCREENING
 The first devices used to measure blood alcohol content
in individuals suspected of “driving under the influence,”
made use
 The original breath analyzer test measured alcohol
concentration in expired air by the color change occurring
when the bright-orange oxidizing agent potassium
dichromate (K2Cr2O7) reduced to blue-green
chromium(III).
ETHANOL, THE MOST
WIDELY ABUSED DRUG
 Throughout history, humans drank lcoholic beverages for their pleasant taste
and the feeling of euphoria.
 In the beginning alcohol is a stimulant, largely because small amounts
decrease social inhibitions, the ethanol (CH3CH2OH) in an alcoholic
beverage, actually depresses the central nervous system.
 The chronic and excessive consumption of alcoholic beverages has become
a major health and social crisis, making ethanol the most widely abused drug
in the United States.

One estimate suggests that there are 40 times more alcoholics than heroin
addicts.
Ethers
 Ethers are organic compounds that have two alkyl
groups bonded to an oxygen atom. These two alkyl
groups can be the same, or they can be different.
Ethers have higher melting points and boiling
points than hydrocarbons of comparable
size and shape.
Ethers have lower melting points and boiling
points than alcohols of comparable size
and shape.
Naming
FOCUS ON HEALTH & MEDICINE
ETHERS AS ANESTHETICS
 Diethyl ether...
 Common anesthetic today
 The discovery that diethyl ether
(CH3CH2OCH2CH3) is a general anesthetic
revolutionized surgery in the nineteenth century.
Alkyl Halides
 Alkyl halides are organic molecules containing a halogen
atom X (X = F, Cl, Br, I) bonded to a tetrahedral carbon atom.
Alkyl halides are classified as primary (1°), secondary (2°), or
tertiary (3°) depending on the number of carbons bonded to the
carbon with the halogen.
Properties
 Alkyl halides contain a polar bond, but since they have all of their
hydrogens bonded to carbon, they are incapable of intermolecular
hydrogen bonding.
 Alkyl halides with one halogen are polar molecules, because they
contain a net dipole. As a result, they have higher melting points and
boiling points than alkanes with the same number of carbons.
Naming
 In the IUPAC system, an alkyl halide is named as an
alkane with a halogen substituent—that is, as a halo
alkane. To name a halogen substituent, change the -ine
ending of the name of the halogen to the suffi x -o (e.g.,
chlorine → chloro).
FOCUS ON THE ENVIRONMENT
ALKYL HALIDES AND THE OZONE LAYER
 Chlorofluorocarbons (CFCs) are simple halogencontaining compounds having the general molecular
structure CFxCl4 – x. CFCs are manufactured under the
trade name Freons.
 Two examples are CFCl3 (Freon 11) and
CF2Cl2 (Freon 12).
 CFCs are inert and nontoxic, and they have been used
as refrigerants, solvents, and aerosol propellants.
 Because CFCs have low boiling points and are water
insoluble, they readily escape into the upper atmosphere.
There, CFCs are decomposed by sunlight. This process
forms highly reactive intermediates that have been
shown to destroy the ozone layer (See figure)
ORGANIC COMPOUNDS THAT
CONTAIN SULFUR
Thiols are organic compounds that contain a
sulfhydryl group (SH group) bonded to a tetrahedral
carbon.
Thiols Vs Alcohols
Importance
 The chemistry of thiols and disulfides plays an important
role in determining the properties and shape of some
proteins, as we will learn in Chapter 21.
 For example, α-keratin, the protein in hair, contains many
disulfi de bonds. Straight hair can be made curly by
cleaving the disulfi de bonds in α-keratin, then
rearranging and re-forming them, as shown schematically
in Figure 14.7.
Readings
 Book chapter 14