LOGO
Lecture 5 :
Unsaturated Hydrocarbons
Organic Chemistry – FALL 2015
Course lecturer :
Jasmin Šutković
11 November 2015
Contents
International University of Sarajevo
Book chapter 13
13.1 Alkenes and Alkynes
13.2 Nomenclature of Alkenes
and Alkynes
13.3 Cis–Trans Isomers
13.4 Interesting Alkenes in
Food and
Medicine
13.5 FOCUS ON HEALTH &
MEDICINE:
Oral Contraceptives
13.6 Reactions of Alkenes
13.7 FOCUS ON HEALTH &
MEDICINE:
Margarine or Butter?
13.8 Polymers—The Fabric of
Modern
Society
13.9 Aromatic Compounds
13.10 Nomenclature of Benzene
Derivatives
13.11 FOCUS ON HEALTH &
MEDICINE:
Aromatic Drugs, Sunscreens, and
Carcinogens
13.12 FOCUS ON HEALTH &
MEDICINE:
Phenols as Antioxidants
Introduction
In organic chemistry, a saturated compound is a chemical
compound that has a chain of carbon atoms linked together
by single bonds and has hydrogen atoms filling all of the
other bonding orbitals of the carbon atoms.
Alkanes are an example of saturated compounds.
An unsaturated compound is a chemical compound that
contains carbon-carbon double bonds or triple bonds, such
as those found in alkenes or alkynes, respectively.
Alkenes
Ethylene is a plant hormone, regulating growth and
fruit rippening.
Common fetures ?
CIS – TRANS isomers
Chapter 12 covers isomers ....
In allkenes and alkynes we face the same
fenomena...
Stereo- Isomers
 2 butane can have two arrangements around the atom !
Naming
Interesting alkenes in food
and medicine
 Lycopene – antioxidant – preventing
unwanted oxidation reaction to occure
 Decreses risk of heart disease
 Found in many food – tomato products
Cancer drugs
 Tamoxifen- a potential anticancer drug –
containing double bonds with additional
functional groups
 Requires female hormone – estrogen to
react- used for Breast cancer treatment
Reaction of Alkenes
 Addition reaction
Hydrogenation
 Addition of hydrogen grouphydgrogenation
Halogenation
 Addition of halogen elements- halogenation
HYDROHALOGENATION
 ADDITION OF HYDROGEN HALIDES
 Hydrohalogenation is the addition of HX (X = Cl or Br)
to an alkene.
Hydration
 Addition of water (H2O)
FOCUS ON HEALTH & MEDICINE
MARGARINE OR BUTTER?
 One addition reaction of alkenes, hydrogenation, is especially
important in the food industry.
 It lies at the heart of the debate over which product, butter or
margarine, is better for the consumer.
 Butter – long C chain – single bonds = solid at room temperature,
made from milk- saturated hydrocarbon.
 Margarine – synthetic- mimics the taste of butter- composed mainly
of partially hydrogenated vegetable oils formed by adding hydrogen
to the double bonds in the carbon chain derived from unsaturated
fatty acids.
Facts .... ??????
 Soem say that Margarine usually tops butter when it comes to heart
health.
 Margarine is made from vegetable oils, so it contains no cholesterol.
Margarine is also higher in "good" fats — polyunsaturated and
monounsaturated — than butter is. These types of fats help reduce
low-density lipoprotein (LDL), or "bad," cholesterol !!!
But...Some Margarines may contain trans fat ...not healthy- supporting
the increase of cholesterol in blood!!!
 Butter, on the other hand, is made from animal fat and so in its
structure contains cholesterol and high levels of saturated fat.
Why Butter ....?
 There are a lot of fat soluble vitamins in butter (Vitamin A,E and K)
 Butter Contains a Lot of Healthy Saturated Fats
 Butter Lowers Heart Attack Risk Compared to Margarine
(Margarine significantly increased the risk of cardiovascular disease, while
butter had no effect. - http://wholehealthsource.blogspot.com/2009/10/butter-vsmargarine-showdown.html)
 Butter is a Good Source of The Fatty Acid Butyrate
The 4-carbon fatty acid butyrate is created by bacteria in the colon when they
are exposed to dietary fiber.This may be the main reason fiber has health
benefits for humans.)
 Butter is Rich in Conjugated Linoleic Acid (CLA)
(This fatty acid has powerful effects on metabolism and is actually sold
commercially as a weight loss supplement)
 Butter is Associated With a Lower Risk of Obesity
Butter is Delicious
Butter or Margarine ?
 Which should you choose—butter or margarine—and if
it’s margarine, which of the many varieties is best for
you? Margarine can be hard or soft. It can be made from
olive oil, corn oil, safflower oil, or even yogurt.
 One fact remains clear to nutritionists. It is best to limit
your intake of both butter (high in saturated fat) and
margarine (high in trans fat).
Important
 The saturated fatty acids increase the levels of
bad cholesterol (LDL) and clog the arteries –
heart or brain stroke !!!
 STOP---It was never really proven that it caused
any harm, but dissproven in many recent studies
!
 http://wholehealthsource.blogspot.com/200
9/10/butter-vs-margarine-showdown.html
 Unsaturated fatty acids increase the levels of
good cholesterol (HDL) by taking the LDL to the
liver to be broken down and removed from the
body.
 Too much saturated fat can increase the amount
of cholesterol in the blood, which can increase
the risk of developing coronary heart disease.
POLYMERS—THE FABRIC
OF MODERN SOCIETY
 Polymers are large molecules made up of repeating units of
smaller molecules—called monomers—covalently bonded
together.
 Polymers include the naturally occurring proteins that compose hair,
tendons, and fingernails.
 They also include such industrially important plastics as
polyethylene, poly(vinyl chloride) (PVC), and polystyrene.
 Since 1976, the U.S. production of synthetic polymers has exceeded
its steel production.
 Soft drink bottles, plastic bags, food wrap, compact discs, Teflon,
and Styrofoam are all made of synthetic polymers.
Polymerisation
Aromatic compounds
 Aromatic compounds were originally named because
many simple compounds in this family have characteristic
smell. Today, the word aromatic refers to compounds
that contain a benzene ring, or rings that react in a
similar fashion to benzene.
 Benzene, the simplest and most widely known aromatic
compound, contains a six-membered ring and three
double bonds. Since each carbon of the ring is also
bonded to a hydrogen atom, the molecular formula for
benzene is C6H6.
 Each carbon is surrounded by three groups, making it
trigonal planar. Thus, benzene is a planar molecule,
and all bond angles are 120°.
Nomenclature
 To name a benzene ring with one substituent, name the
substituent and add the word benzene.
 Carbon substituents are named as alkyl groups.
 When a halogen is a substituent, name the halogen by
changing the -ine ending of the name of the halogen to
the suffi x -o; for example, chlorine → chloro.
Suncreens
Focus on health
 A wide variety of phenols, compounds that contain a
hydroxyl group bonded to a benzene ring, occur in
nature.
 Vanillin from the vanilla bean and eugenol from cloves
are both phenols.
 Curcumin is a yellow pigment isolated from turmeric, a
tropical perennial in the ginger family and a principal
ingredient in curry powder. Curcumin has long been used
as an anti-infl ammatory agent in traditional eastern
medicine.
Nuts
Nuts – rich in antioxidants , like
phenols
Reminder- Antioxidant!
 An antioxidant is a molecule that inhibits
the oxidation of other molecules.
 Oxidation reactions can produce free
radicals. In turn, these radicals can
start chain reactions. When the chain
reaction occurs in a cell, it can cause
damage or death to the cell.
 Antioxidance stops these reactions !
Readings
Book Chapter 13