DIENES

Reporters:
Luis, Shavemil R.
Mendevil, Angielyn
Oquialda, Joan S.
Sario, Angelo
Sentillas, Aljhon
 DIENES
Is a covalent compound that contains two
double bonds, usually among carbon atoms. They
thus contain two alkene units, with the standard
prefix di of systematic nomenclature. As subunit
of more complex molecules, dienes occur in
naturally occurring and synthetic chemicals and
are used in organic synthesis.
 DIFFERENT KINDS OF DIENES

Dienes can divided into three classes:

• Cumulated dienes (cumulenes) have the double bonds

sharing a common atom as in a group of compounds
called allenes.
• Conjugated dienes have conjugated double bonds
separated by one single bond
• Unconjugated dienes have the double bonds separated
by two or more single bonds. These are also known as
Isolated dienes.
STRUCTURES
 STRUCTURE AND NOMENCLATURE OF DIENES

Dienes are simply alkenes that contain

two carbon – carbon double bonds.
Therefore they have essentially the same
properties are in the alkenes. And we shall
say applied equally well to compounds
with more than two double bonds.
 STRUCTURE OF DIENES

Dienes are classified as cumulated,

isolated, or conjugated; conjugated
dienes are more stable than isolated
dienes because of electron
delocalization over the \pi(π) system.
 STRUCTURE OF DIENES

• Compounds with double bonds are known as alkenes,

and those that contain more than one double bond are
known as polyalkenes. The simplest type of polyalkene
is a diene, a compound containing two double bonds (or
a 4\pi4π-electron system). These double bonds may be
arranged in a variety of ways and are classified based on
their arrangement in the overall molecule.
 STRUCTURE OF DIENES

• Dienes are divided into three classes:

The two important class according to the arrangement the double bonds as below.
a. A conjugated diene is a diene with two double bonds that are separated by one single
bond.
b. An isolated diene is a diene with two double bonds that are separated by two or more
single bonds.
 STRUCTURE OF DIENES

c. A cumulated diene is a diene with two successive

double bonds without an intervening single bond.
NAMING OF DIENES
 NAMING OF DIENES

• Dienes- organic compound containing 2 separate carbon to carbon double bonds C=C
• The rule for naming is they all end with “-diene”.
• To name diene, we will use the same rules we learned for naming alkenes and with
IUPAC nomenclature.
• This includes finding the longest chain with other double bonds while giving them
the lowest priority possible (including other substituents)
• The only difference would be that instead of suffix “-ene”, we would now say “—diene”
and after the prefix “hex-” we add the letter “a”. For example: 2,4-hexadiene.
•  
• The general formula of diene is , n is the
number of carbons is used to determine the
number of hydrogen atoms. Example n=4, so
H= (2(4)-2)= 6
C4H6
 NAMING OF DIENES

Dienes are ISOMERS of Alkynes (same general formula)

Naming compounds- Again, ignore all the hydrogen’s. We only worry about carbon atoms.
Rule#1 – Name longest chain that contains both double bonds. End with “diene”
Rule#2- When necessary use the lowest numbers to give the locations of both double bonds.
 NAMING OF DIENES

How to name dienes?

 changing “-ene” of alkanes by “-diene”.
The position of the double bonds are numbered to give the first carbon of each
double bond a minimum number.
Example:

CH2=CH-CH=CH2 1,3-butadiene

CH2=C=CH2
1,2- propadiene
 CLASSIFICATION OF DIENES

How to classify dienes?

 Isolated dienes (or) Non conjugated dienes
- double bonds are separated by more than one single bond.
Example:
CH2=CH-CH2-CH=CH2
1,4- Pentadiene
 Conjugated dienes
- double bonds are separated by one single bond
Example:
CH2=CH-CH=CH2
1,3- Butadiene
 CLASSIFICATION OF DIENES

Cumulated diene
- double bonds are adjacent to each
other
Example:
CH2=C=CH2
1,2- Propadiene
 IUPAC
(INTERNATIONAL UNION OF PURE AND APPLIED CHEMISTRY)

NOMENCLATURE OF
DIENES
 NOMENCLATURE OF DIENES

Dienes are named by the IUPAC system in the same way as alkenes, except at the ending diene is used ,
with two number of indicate the positions of the two double bonds. This system is easily extended to
compounds containing any number of double bonds.
Example:

two double bonds= diene

The name of a substituent is stated before the name of the longest continuous chain that contains the functional
group, together with a number to designate the carbon to which the substituent is attached. If a compound’s
name contains both a functional group suffix and a substituent, the functional group suffix gets the lowest
possible number.
 IUPAC NOMENCLATURE OF
DIENES

1. Find the Longest chain containing both

double bonds
 IUPAC NOMENCLATURE OF
DIENES

2. Use corresponding alkane name but

replace the “ne” ending with “diene”
 IUPAC NOMENCLATURE OF
DIENES

Number in the direction that gives the lowest number

3.

to a double bond
 IUPAC NOMENCLATURE OF
DIENES

4. List substituents in alphabetical order

 IUPAC NOMENCLATURE OF
DIENES

5.Place numbers indicating the double bond positions either

in front of the parent compound or in the middle of the name
immediately before the diene suffix
IUPAC NOMENCLATURE OF DIENES
REACTION OF CONJUGATED
DIENE

By: Angelo Sario

 REACTION OF CONJUGATED
DIENE

•The difference b/n conjugated and isolated double bond is in

their electrophilic addition reactions
•Conjugated dienes undergo electrophilic addition reaction
readily, but mixture of product are invariably obtained.
•Addition of HBr to buta-1,3-diene for instance yields a
mixture of two product
3-bromobut- 1- ene(71%;1,2- addition)
• Is a typical
Markovnicov product
of 1,2 addition to a
double bond
1-Bromobut -2-ene(29%;1,4-addition)
• Appear unusual.
• The double bond in this
product has moved to a
position between carbons 2
and 3, and HBr has added to
carbons 1 and 4, a result
describe as 1,4- addition.
•How can we account for the formation of the 1,4-addition product?
• an allylic carbocation is involved as an intermediate or
development
• allylic means next to a double bond

• when buta-1,3 diene reacts with an electrophile such as H+, two

carbocation intermediates are possible. a primary carbocation and
a secondary allylic cation.
When the allylic cation reacts with br- to complete the electrophilic addition,
reaction can occur either at c1 or at c3 because carbons share the positive charge
A mixture of 1,2 – and 1,4-addition products results.
POLYMER

By: Aljhon Sentillas

 CONTENT

1. INTRODUCTION
2. TYPES OF POLYMERS
3. CLASSIFICATION OF POLYMERS
4. CHARACTERISTICS OF POLYMERS
5. APPLICATION OF POLYMERS
 INTRODUCTION

•  
 Polymer are very large molecules made when hundreds of “Monomers”
join together to form long chains.
 The word Polymers is combination of two Greek Words, “Poly” means
“many” and “meros” meaning “Parts or Units”
 Polymer is used as a synonym for plastic.
 All plastics are polymers, but not all polymers are plastics.

N(CH2-CH2) (-CH2-CH2-
Ethylene Polyethylene
 TYPES OF POLYMERS

Natural Polymers
Homopolymer
Copolymer
Thermoplastics
Thermosets
Long Chain Polymers
 NATURAL POLYMER
 Definition: Natural polymer is a polymer that results from only raw
materials that are found in nature.
 Some of these natural polymers include DNA and RNA
 Cotton, DNA, Wool, Wood are some of the naturally occurring
polymers.
 HOMOPOLYMER
• Homopolymers are synthesized from a single type of monomer.
• Homopolymers are consists of chains with identical bonding
linkages to each monomer unit.
• This usually implies that the polymer is made from all identical
monomer molecules.
 COPOLYMER
• When two or more different monomers together to polymerize their result is
called as copolymer.
• This process is called as copolymerization.
• Types of Copolymer:
1) Statistical copolymer
2) Alternating copolymer
3) Block copolymer
4) Graft copolymer
 THERMOPLASTIC
• A type of plastic that can be softened by heat,
hardened by cooling, and then softened by heat over
and over again
• Thermoplastic are not cross- linked polymer.
• Examples: Polyethylene, Nylon, Polyvinyl chloride.
 THERMOSETS
Thermosets having the property of becoming permanently hard and
rigid when heated.
• Thermosets are hard and rigid at room temperature and do not soften
on heating.
• Examples: Epoxy resins, Phenolic resins, Unsaturated polyester resins.
 LONG CHAIN POLYMERS

• A very long strand of repeating

molecules linked together by primary
bond.
• Polymer chains are orient themselves in
lines as they enter a mold but may be
annealed so they can recoil.
 CLASSIFICATION OF POLYMER

CLASSIFICATION OF
POLYMER

Based on origin of Based on molecular Based on mode of

Based on structure
source forces polymerisation
1. Natural
1. Linear polymers 1. Elastomers 1. Addition polymers
polymers

2. Semi- 2. Branched chain 2. Fibers 2. Condensation

synthetic polymers polymers

3. Synthetic 3. Cross-linked 3. Thermoplastics

polymer polymers
4. Thermosetting
polymers
 CLASSIFICATION BASED ON
SOURCE

1. NATURAL POLYMER-Polymers which are isolated from natural materials

are called as Natural Polymers. E.g. Cotton, Silk, Wool, Rubber.
2. SYNTHETIC POLYMER- Polymers which are synthesized from low
molecular weight compounds are called as Synthetic Polymers. E.g.: Polyethylene,
nylon, terylene.
3. SYNTHESIS POLYMERS- These polymers are mostly derived from naturally
occurring polymers by chemical modification. E.g.: Rayon
 BASED ON STRUCTURE

• Linear Polymer: Molecules from long chains without branches

• Branched Polymer: Molecules having branch points

that connect 3 or more segments.

• Cross-Linked Polymer: It includes interconnections

between chains

• Network Polymer: A cross linked polymer that

includes numerous interconnections between chains.
 BASED ON MODE OF
POLYMERISATION

Additional Polymerization:
 Same kind of monomers are straight forwardly added.
 It is rapid chain reaction having chemically activated mers.
 Each reaction sets up the condition for another to proceed.
 It consists of 3 stages:

Initiation Propagation Termination

(Birth) (Growth) (Death)
 CHARACTERISTICS OF POLYMER

• Low density
• Low coefficient of friction
• Good corrosion resistance
• Good mould ability
• Poor tensile strength
• Low mechanical properties
• Poor temperature resistance
• Can be produced transparent or different colours
 APPLICATION

• Medicine: Many biomaterials especially heart valve replacements and blood

vessels are made up polymers like Dacron, Teflon
• Consumer Science: Plastic containers of all shapes and sizes are light weight and
economically less expensive than more traditional containers.
• Industry: Automobile parts, pipes, tanks, packing material, adhesives are all
polymer application used in industrial market.
• Sports: Playground equipment, golf clubs, swimming pools and protective
helmets are produced from polymers.
POLYMERZATION

By: Angielyn Mendevil

 A BRIEF HISTORY

The Polymerization of conjugated dienes

with transition-metal-based catalysts began in
1954 at the laboratories of the Polytechnic of
Milan directed by Prof. Giulio Natta.
 HOW TO CALCULATE THE DEGREE
OF POLYMERIZATION

A degree of polymerization is a key characteristic polymers that

determine physical properties of polymer materials. Polymers are large
molecules that consist of repeating structural (monomer) units. For
example, polyethylene is composed of repeating units (CH2-CH2)n
where “n” is an integer number that indicates the degree of
polymerization.
•  
• Write down the chemical formula of the polymer.
For example, if the polymer is tetrafluoroethylene
then its formula is –(CF2-CF2-. The monomer unit is
placed in parentheses.
• Obtain atomic masses of the elements that compose
the monomer unit molecule, using the periodic table
elements. For tetrafluoroethylene, the atomic masses
of carbon (C) and fluorine (F) are 12 and 19,
respectively.
• Calculate the molecular weight of the monomer unit by
multiplying the atomic mass of each element by the number
of atoms in the monomer of each, then add the products. For
tetrafluoroethylene, the molecular weight of the monomer
units is 12 x 12 + 19 x 4= 100
• Divide the molecular weight of the polymer by the
molecular weight of the monomer unit to calculate the
degree of polymerization. If the molecular mass of
tetrafluoroethylene is 120,000, its degree of polymerization
is 120,000 / 100 = 1,200.
 Conjugated dienes (alkenes with two double bonds
and single bond in between) can be polymerized to
form important compounds like rubber. This takes
place in different forms, both in nature and in the
laboratory. Interactions between double bonds on
multiple chains leads to cross-linkage which creates
elasticity within the compound.
 POLYMERIZATION OF 1,3- BUTADIENE

For rubber compounds to be synthesized. 1,3-

butadiene must be polymerized. Below is a simple
illustration of how this compound is formed into a
chain. The 1,4 polymerization is much more
useful to polymerization reactions.
 SYNTHETIC RUBBER

The most important synthetic rubber is Neoprene

which is produced by the polymerization of 2- chloro-
1,3 butadiene.
 NATURAL RUBBER

The synthesis of rubber in nature in somewhat similar the artificial

synthesis of rubber except that it takes place within a plant. Instead of
the 2-chloro-1,3-butadiene used in the synthesis of neoprene. Natural
rubber is synthesized from 2-methyl -1,3-butadiene. As an electrophile
the plant synthesizes the pyrophosphate 3-methyl-3-butenyl
pyrophosphate is from phosphoric acid and 3-methyl-3-buten-1-ol.
This pyrophosphate then catalyzes the reaction that leads to natural
rubber.
• The 3-methyl-3-butenyl pyrophosphate (OPP) is the used
in the polymerization of natural rubber as it pulls electrons
off 2-methyl-1,3-butadiene.
THANK YOU!!!