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Lesson title: Unsaturated Hydrocarbon ( Alkenes, Materials:
Cycloalkenes, Alkynes) Pen and SAS
Lesson Objectives: At the end of the module, you should be able to:
1. Draw the structures of alkenes, cycloalkenes and alkynes References:
based on the IUPAC nomenclature. General, Organic and
2. Determine the correct catalyst or reagent in the conversion of Biological Chemistry 6th Ed
unsaturated hydrocarbons.
(Stoker, 2013)
Productivity Tip:
Clear your mind. Take a few minutes before you start the module, or between pages, to close your eyes and
clear your mind of everything else.
A. LESSON PREVIEW/REVIEW
Introduction (2 mins)
In our previous module we learned that there are two general types of hydrocarbons exist,
saturated and unsaturated hydrocarbons. Unsaturated hydrocarbon contain one or more carbon-carbon
multiple bonds. There are three classes of unsaturated hydrocarbons: the alkenes, alkynes and aromatic
hydrocarbons.
Activity 1: What I Know Chart, part 1 (5 mins)
Instructions: In this chart, reflect on what you know now. Do not worry if you are sure or not sure of your
answers. This activity simply serves to get you started on thinking about our topic. Answer only the first
column, ‘What I Know”. Leave the third column “What I Learned” blank at this time.
What I Know Questions: What I Learned (Activity 4)
1. What is unsaturated
hydrocarbon?
21What is the difference between
alkenes and alkynes.
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3. How to name alkenes,
Cycloalkenes and alkynes?
B.MAIN LESSON
Activity 2: Content Notes (40 mins)
Unsaturated hydrocarbon is a hydrocarbon in which one or more carbon-carbon multiple bonds (double bond,
triple bonds, or both) are present. They have physical properties similar to those of saturated hydrocarbons;
however their chemical properties are much different. Unsaturated hydrocarbons are more reactive than their
unsaturated counterparts. Carbon-carbon multiple bonds are the functional group for an unsaturated
hydrocarbon. Functional group is the part of an organic molecule where most of its chemical reactions occur.
Unsaturated hydrocarbons are subdivided into three groups on the basis of the type of multiple bond(s) present:
ALKENES – which contain one or more carbon-carbon double bonds. ALKYNES – which contain one or more
carbon-carbon triple bonds. AROMATIC HYDROCARBONS – which exhibit a special type of “delocalized”
bonding that involves a six membered carbon ring.
CHARACTERISITICS OF ALKENES, CYCLOALKENES AND ALKYNES
ALKENE is an acyclic unsaturated hydrocarbon that contains one or more carbon-carbon double bonds.
The alkenes functional group is (C=C) group. Names end in “ene”The ene ending means a double bond is
present.General formula CnH2n. The two simplest alkenes are: Ethane (CH2=CH2) and Propene (
CH2=CHCH3)
CYCLOALKENES is a cyclic unsaturated hydrocarbon that contains one or more carbon-carbon double
bonds within the ring system. General formula CnH2n-2 The simplest cycloalkene is the compound
cyclopropene ( C3H4)
IUPAC NOMENCLATURE FOR ALKENES AND CYCLOALKENES
RULE:
1. Replace the suffix –ane with the suffix –ene, which is used to indicate the presence of a
carbon-carbon double bond.
RULE:
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2. Select as the parent carbon chain the longest continuous chain of carbon atoms that contains
both carbon atoms of the double bond.
RULE
3. Number the parent carbon chain beginning at the end nearest the double bond.
If the double bond is equidistant from both ends of the parent chain, begin numbering from the
end closer to a substituent.
RULE:
4. Give the position of the double bond in the chain as a single number, which is the lower-
numbered, carbon atom participating in the double bond.This number is placed immediately
before the name of the parent carbon chain.
1-Chloro-2-butene 2,3-Dimethyl-1-butene
2,2,4-Trimethyl-3-hexene 4-Cyclopropyl-1-butene
RULE:
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5. Use the suffixes –diene, -triene, tetraene, -pentaene, and so on when more than one double
bond is present in the molecule. A separate number must be used to locate each double bond
1, 3-Butadiene 3-Methy-1,4-pentadiene
2,3,4-Trimethyl-1,3,6-octatriene 2,6-Dichloro-1,3,5-heptatriene
RULE:
6. A number is not needed to locate the double bond in unsubstituted cycloalkenes with only
one double bond because that bond is assumed to be between carbons 1 and 2.
Cyclohexene Cyclopentene 1,4-Cyclohexadiene 1,3,5-Cyclooctatriene
Rule:
7. In substituted cycloalkenes with only 1 double bond, the double-bonded carbon atoms are
numbered 1 and 2 in the direction (clockwise or counterclockwise) that gives the first-
encountered substituent the lower number. Again, no number is used in the name to
locate the double bond.
Cyclohexene 4-Methylcyclohexene 3-Bromocyclohexen 3-Ethyl-4-methylcyclohexene
Rule:
8. In cycloalkenes with more than one double bond within the ring, assign one double bond the
numbers 1 and 2 and the other double bonds the lowest numbers possible.
1,4-Cyclohexadiene 5-Chloro-1,3-cyclohexadiene
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Alkenes as Substituents
An alkenyl group is a noncyclic hydrocarbon substituent in which a carbon-carbon double bond
is present. The three most frequently encountered alkenyl groups are the one, two, and three-carbon entities,
which may be named using IUPAC nomenclature ( methylidene, ethenyl, and propenyl) or with common names
( methylene, vinyl, and allyl)
CH2 CH2=CH CH2=CH – CH2
Methylene Group Vinyl group Allyl group
(IUPAC name: Methylidene group) (IUPAC name: ethenyl group) (IUPAC name: 2-propenyl group)
The use of these alkenyl group names in actual compound nomenclature is illustrated in the following
examples:
Naturally Occurring Alkenes
Alkenes are abundant in nature. Many important biological molecules are characterized by the presence of
carbon-carbon double bonds within their structure. Two important types of naturally occurring substances to
which alkenes contribute are:
Pheromones is a compound used by insects (and some animals) to transmit a message to other members of
the same species. Pheromones are often alkenes or alkene derivatives. Insect sex pheromones are useful in
insect control.
Terpenes is an organic compound whose carbon skeleton is composed of two or more 5-carbon structural units.
Isoprene (2-methyl-1,3-butadiene) is a five carbon diene. Terpenes are among the most widely distributed
compounds in the biological world, with over 22,000 structures known.
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Selected terpenes containing two isoprene units
Three isoprene units
Eight Isoprene units
Physical Properties of Alkenes and Cycloalkenes
The general physical properties of alkenes and cycloalkenes include: solubility in water, solubility in nonpolar
solvents, and densities lower than water. Thus they have physical properties similar to those of alkanes. The
melting point of an alkene is usually lower than that of the alkane with the same number of carbon atoms. Alkene
with 2 to 4 carbon atoms are gases at room temperature. Unsubstituted alkenes with 5 to 17 carbon atoms and
one double bond are liquids, and those with still more carbon atoms are solids.
Chemical Reactions of Alkene
Combustion reaction: the combustion product as with any hydrocarbon, are carbon dioxide and water.
C2H4 + 3O2 2CO2 + 2H2O
Addition reactions: is a reaction in which atoms or groups of atoms are added to each carbon atom of a
carboncarbon multiple bonds in a hydrocarbon or hydrocarbon derivative.
Addition reaction can be classified into two:
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Symmetrical addition reaction: is an addition reaction in which identical atoms (or groups of atoms) are
added to each carbon of a carbon-carbon multiple bond.
Two most common examples of Symmetrical addtition reaction are:
Hydrogenation reaction: is an addtition in which hydrogen is incorporated into molecule of an organic
compound.
Halogenation Reaction: is an addition reaction in which a halogen is incorporated into molecules of an
organic compound. In alkene halogenation, a halogen atom is added to each carbon atoms of a double bond.
Chlorination and Bromination are the two halogenations processes most commonly encountered. No catalysts
are needed.
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Unsymmetrical addition reaction: is an addition reaction in which different atoms (or groups of atoms) are
added to the carbon atoms of a carbon-carbon multiple bond.
Two important types of Unsymmetrical addition reaction are:
Hydrohalogenation: is an addition reaction in which a hydrogen halide (HCl, HBr, or HI) is incorporated into
molecules of an organic compound.
Hydration Reaction: is an addition reaction in which H20 is incorporated into molecules of an organic
compound.
ALKYNES
Represent the second class of unsaturated hydrocarbons. Is an acyclic unsaturated hydrocarbon that
contains one or more carbon-carbon triple bonds. As the family name alkyne indicates the characteristics ending”
associated with a triple bond. The general formula of an alkyne with one triple bond is C nH2n-2
IUPAC nomenclature for Alkynes
The rules for naming are identical to those used to name alkenes. EXCEPT the ending –yne is used
instead of –ene.
Example:
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1-Hexyne 2,2-Dimethyl-3-heptyne
Activity 3: Skill-building Activities (with answer key) (30 mins + 5 mins checking)
A- Instructions: Explain why each name is incorrect, and then write a correct name. Check your answers against
the Keys to Correction found at the last pages of this SAS. Write your score.
1. 1-Methylpropene
2. 3-Pentene
2. 2-Methylcyclohexene
4. 3,3- Dimethylpentene
5. 4-Hexyne
B- Instructions: What reagent and/or catalysts are necessary to bring about each conversion?
Br
1. CH2-CH=CH-CH3 + ____ CH3-CH2-CH-CH3
CH3 CH4
2. CH3-C=CH2 + ___ CH3-C-CH3
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OH
I
3. + ___
CH3 CH3
4. CH3- C=CH3+___ CH3 - C - CH2
Br Br
Activity 4: What I Know Chart, part 2 (3
mins)
Instruction: To review what was learned from this session, please go back to Activity 1 and answer the “What I
Learned “column. Notice and reflect on any changes in your answer.
Activity 5: Check for Understanding (30 mins)
Instructions: Write the IUPAC name for each unsaturated hydrocarbons.
1.
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2.
3.
4.
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5.
Note: Answers will be provided and discussed by the instructor.
C. LESSON WRAP-UP
Activity 6: Thinking about your Learning (5 mins)
A. Work Tracker: You are done with this session! Let’s track your progress. Shade the session
number you just completed.
P1 P2
1 2 3 4 5 6 7 8 9 10
B. Think about your Learning
Tell me about your thoughts in this module! What are your insights of this topic? Did you gain
new information?
FAQs
1. What is polymerization reaction?
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It is a chemical reaction in which the repetitious combining of many small molecules (monomers)
produces a very large molecule (the polymer ). With appropriate catalysts, simple alkenes and simple
substituted alkenes readily undergo polymerization.
2. What is addition polymer?
It is a polymer in which the monomers simply “add together” with no other products formed nm besides
the polymer.
KEY TO CORRECTIONS for Activity No. 3:
A- Instructions: Explain why each name is incorrect, and then write a correct name:
1. 1-Methylpropene
Ans. The longest chain is four carbons. The correct name is 2-Butene
2. 3-Pentene
Ans. The chain is not numbered correctly. The correct name is 2-Pentene
3. 2-Methylcyclohexene
Ans. The ring is not numbered correctly. The correct name is 1-Methylcyclohexene
4. 3,3- Dimethylpentene
Ans. The double bond must be located. The correct name is 3,3-Dimethyl-1- pentene
5. 4-Hexyne
Ans. The chain is not numbered correctly. The correct name is 2-Hexyne.
B- Instructions: What reagent and/or catalysts are necessary to bring about each conversion?
Br
1. CH2-CH=CH-CH3 CH3-CH2-CH-CH3 Ans. HBr
CH3 CH4
2. CH3-C=CH2 CH3-C-CH3 Ans. H2O/H2SO4
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OH
I
3. Ans. HI
CH3 CH3
4. CH3- C=CH3 CH3 - C - CH2 Ans. Br2
Br Br
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