9

Consumer
Chemistry
Quarter 1 – Module 5:
Alkynes : Unsaturated
Hyrocarbons
Consumer Chemistry – Grade 9-Special Science Program
Alternative Delivery Mode
Quarter 1 – Module 5: Alkynes: Unsaturated Hydrocarbons
First Edition, 2020

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 9

Consumer
Chemistry
Quarter 1 – Module 5:
Alkynes:Unsaturated
Hydrocarbons
Introductory Message
For the facilitator:

Welcome to the Consumer Chemistry Grade 9 Special Science Program Alternative

Delivery Mode (ADM) Module on Alkynes: Unsaturated Hydrocarbons!

This module was collaboratively designed, developed and reviewed by educators both
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2
For the learner:

Welcome to the Consumer Chemistry Grade Special Science Program Alternative

Delivery Mode (ADM) Module on Alkynes: Unsaturated Hydrocarbons!

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depict skill, action and purpose. Through our hands we may learn, create and
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What’s In This is a brief drill or review to help you link

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What’s New In this portion, the new lesson will be

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What is It This section provides a brief discussion of the

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What’s More This comprises activities for independent

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answers to the exercises using the Answer
Key at the end of the module.

What I Have Learned This includes questions or blank

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3
 Assessment This is a task which aims to evaluate your
level of mastery in achieving the learning
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to you to enrich your knowledge or skill of the
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module.

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this module.

The following are some reminders in using this module:

1. Use the module with care. Do not put unnecessary mark/s on any part of the
module. Use a separate sheet of paper in answering the exercises.
2. Don’t forget to answer What I Know before moving on to the other activities
included in the module.
3. Read the instruction carefully before doing each task.
4. Observe honesty and integrity in doing the tasks and checking your answers.
5. Finish the task at hand before proceeding to the next.
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If you encounter any difficulty in answering the tasks in this module, do not
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4
 What I Need to Know

This module was designed and written with you in mind. It is here to help you master
the nature of Consumer Chemistry. The scope of this module permits it to be used
in many different learning situations. The language used recognizes the diverse
vocabulary level of students. The lessons are arranged to follow the standard
sequence of the course. But the order in which you read them can be changed to
correspond with the textbook you are now using.

The module is divided into two lessons, namely:

 Lesson 1 – Alkynes: Uses and Nomenclature
 Lesson 2 – Properties and Reactions of Alkynes

After going through this module, you are expected to:

1. Recognizes the uses of alkynes to everyday life;
2. Apply the IUPAC Nomenclature System in naming alkynes; and
3. Recognize the importance of reactions of alkynes to industry and everyday life;

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 What I Know

Choose the letter of the best answer. Write the chosen letter on a separate sheet of
paper.
1. Ethyne is the simplest alkyne, and it is often called …….
a. ethylene b. acetylene C. propylene d. methylene

2. Which of the following is an alkyne used in welding steel and wire?

a. ethylene c. propylene
b. acetylene d. polyethylene

3. Brand name of polychloroprene which is used as substitute for rubber?

a. Teflon c. polystyrene
b. Neoprene d. polyvinyl chloride

4. Which of the following is the suffix ending of an alkyne?

A. -en c. -ene
B. -ane d. -yne

5. In IUPAC nomenclature of alkynes, the lowest possible number should be

assigned to which one of the following?
a. Single bond c. triple bond
b. Double bond d. substituent

6. Which of the following is an alkyne?

a. propane c. propyne
b. propene d. propylene

7. Which of the following is the IUPAC name of CH3-C≡CH?

a. propane c. propyne
b. propene d. propine

8. The characteristic functional group of alkynes is the ____________.

a. Single bond c. triple bond
b. Double bond d. all of these

9. Which of the following is a saturated hydrocarbon?

a. Alkane b. alkyne c. halogen d. alkyl group

10. Alkynes has the general formula CnH2n-2, where n is equal to the number of
_____________ atoms.

a. carbon c. halogen
b. hydrogen c. all of these

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 Lesson
Alkynes: Uses and
1 Nomenclature
Alkynes are aliphatic hydrocarbons and are called unsaturated. Alkynes contain
carbon - to- carbon triple bonds, which is the characteristic functional group.

The simplest alkyne is ethyne and by far the most important alkyne, is much more
often called by its common name, acetylene.

What’s In

The Chemistry of alkynes resembles that of alkenes. Alkynes are less common than
alkenes in naturally occurring materials. Even though the use of alkanes, alkenes
and alkynes may overlap in some cases, each of them is a compound on their own.
Alkanes have single bonds; alkenes have at least one double bond, and alkynes has
at least triple bond in its hydrocarbon structure. Carbon to carbon triple bonds is
contained in a few drugs, including oral contraceptives.

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 What’s New

Uses of Alkynes
One of the industries that uses alkynes the most is in welding industry. The triple
bonds in alkynes are really helpful to weld hard material such as steel and wire.
Therefore, alkynes play important role in welding industry especially in torches
production. In torch production, alkynes come in the form of acetylene also known
as ethyne. Acetylene works by bonding in the compound in welding process to
physically merge two things without causing damage to the core compound of the
material.

Alkynes are very important in the preparation of starting material such as the
highly used polymers. Some derivation of alkylenes work for starting materials in
various compound. For instance, vinyl chloride that is alkynes derivation is starting
material for PVC. Another derivation of alkynes, chloroprene, is a good starting
material in the preparation of rubber neoprene. Neoprene is produced by free-
radical polymerization of chloroprene. Originally produced by American DuPont
Corporation, Neoprene is a brand name of polychloroprene, which is used as
substitute for rubber. Neoprene is entirely waterproof which makes it ideal material
for wetsuits and other gear designed to insulate against wet and cold environments.

Molecular Formula
Alkynes have the general formula: CnH2n-2, where n is equal to the number of
carbon atoms.

Now, try completing the following table, the first one is done for you.

No. of C - atoms Molecular Formula

2 C2H2
3
4
5
6
7
8
9
10

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HC≡CH CH3-C≡CH CH3-CH-C≡C-CH3
I
CH 3

Ethyne Propyne 4- Methylpent-2-yne

Acetylene 4-Methyl-2-pentyne

Higher Alkynes, Nomenclature

The alkynes are named according to two systems. In one, names are derived from
acetylene; the other is the IUPAC Nomenclature system.
Acetylene Derived Name of Alkynes
Acetylene derived name is derived from acetylene by replacement of both hydrogen
atoms by alkyl group.
Examples

HC≡C-CH2-CH3

Acetylene ethyl

The above alkyne is named by naming the alkyl group followed by the
acetylene group, Ethylacetylene

CH3 - C ≡ C - CH3

methyl acetylene methyl

two methyl groups are on both sides of the acetylene group, thus, it is named as
dimethylacetylene
CH3
I
CH3 - C ≡ C - CH - CH3

Methyl acetylene isopropyl

On the left side of acetylene is a methyl group; and on the right is isopropyl group,
thus, it is named as Methylisopropylacetylene.
Note:
When two different alkyl groups are on the sides of acetylene group, they are
named from smaller to larger.
In some books, acetylene derived name is referred to as common name of alkyne

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 What is It

Activity 1. IUPAC Nomenclature of Alkynes

Objectives:
To develop skill in naming straight-chain, branched and substituted alkynes
base on the IUPAC nomenclature system/
All alkynes end in yne
Procedure:
Part I: Straight-chain alkynes
For straight-chain alkynes, the name is constructed as

Prefix for number of carbon atoms + yne

Example: CH3 – CH2 – C = CH

1. Count the number of carbons in the group
In this case, there are 4, the prefix is but-

2. Number the carbon chain giving the lowest possible number to the triple
bond
In this case, CH3 – CH2 – C ≡ CH
4 3 2 1
3. Indicate the number of the carbon which contains the triple bond, combine
the prefix but and the suffix -yne

But-1-yne (new IUPAC/preferred name)

1 – Butyne (old IUPAC)

4. Indicate the number of triple bonds with the appropriate prefix, of di, tri-,
tetra-, penta- and insert this before the ending yne

Example: CH3 – C ≡ C – CH2 – C ≡C – CH3

Hept -2,5-diyne (New IUPAC/preferred name)

2, 5-Heptadiyne (old IUPAC )

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Now you try it:
CH ≡ C – CH2 – CH2 – CH3

CH3 – CH2 – C ≡ C – CH2 – C ≡ C – CH3

Part II: Branched/Substituted Alkynes

1. Identify the parent chain. This is the longest continuous sequence of carbon
atoms that includes the triple bond.
Note: The parent chain must include the triple bond even if there is a longer
chain that does not include the triple bond.
CH3
l
CH3 – CH2 – CH – C≡C – CH2 – CH3

2. Decide what groups are attached to the longest chain and name each group
as follows:

Prefix for number of carbons + yl

CH3
l

CH3 – CH2 – CH – C≡ C – CH2 – CH3

In this case, there is a one-carbon group attached, this is a methyl

3. Assign numbers to the carbon in the parent chain giving the lower # to the C
with a triple bond.

CH3
l

CH3 – CH2 – CH – C≡ C – CH2 – CH3

7 6 5 4 3 2 1

4. Construct the IUPAC name by the following formula:

Position where group is attached to longest chain with triple bond

+ prefix for the # of carbons in the group + yl
+ Position of the triple bond
+ prefix for the # of carbons in the longest chain + yne

In this case, its 5-Methylhept-3-yne (5 – Methyl – 3 – heptyne)

11
Now you try it:
Cl CH2 – CH2 – CH2 – CH2 – CH3
l l
CH3 – CH – C ≡ C – CH2 – CH2 – C ≡ CH

Combined Alkenes and Alkynes

If a compound has a double and triple bond then the longest chain is
selected so as to contain the maximum number of double and triple bonds
and is named by replacing the “ane” of the corresponding alkane name by
“en(e), followed by “yne”, “diyne” etc. The “e” is omitted before a vowel or a
“y”. The chain is numbered so as to give the lowest numbers to the double
bonds, then the triple bonds.
Examples:
CH2=CH-C≡CH 1-Buten-3-yne

CH2=CH-C≡C-C=CHCH3 5-Methyl-1,5-heptadien-3-yne
I
CH3

H-C ≡ C - CH2-CH2 - CH= CH-CH3 2-hepten-6-yne

1-Octen-5-yne

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 What’s More

Activity 2. Nomenclature of Alkynes

Name the following structures using modern IUPAC Nomenclature System.
Give the acetylene derived name where applicable
CH2 – CH2 – CH3
l
1) CH3 – C ≡ C –CH –CH2 –CH –CH2 –CH3
l
F

2) CH3 – CH2 – C ≡ C – CH2 – CH2 – CH = CH2

3) CH3 – CH2 - CH – CH2 – C ≡ C – CH3

l
Br

4) CH2 - CH2 - CH2 – C ≡ CH

5)

6) CH3 –CH2- C ≡ C - CH2 – CH3

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 Lesson
Alkenes: Properties and
2 Reactions

What’s In

Properties of Alkynes
Being compounds of low polarity, the alkynes have physical properties that are
essentially the same as those of the alkanes and alkenes. They are insoluble in
water but quite soluble in the usual organic solvents of low polarity: ligroin, ether,
benzene, carbon tetrachloride. They are less dense than water. Their boiling points
increases with increasing carbon number, and the usual effects of chain-
branching. They are very nearly the same as the boiling points of alkanes or
alkenes with the same carbon skeletons

Reactions of Alkynes
The principal reaction of alkynes is addition across the triple bond to form alkanes.
These addition reactions are analogous to those of alkenes

Hydrogenation. Alkynes undergo catalytic hydrogenation with the same catalysts

used in alkene hydrogenation: platinum, palladium, nickel, and rhodium.
Hydrogenation proceeds in a stepwise fashion, forming an alkene first, which
undergoes further hydrogenation to an alkane.

Platinum is used as a catalyst. A catalyst is a substance that hastens a chemical

reaction but does not participate in the actual reaction.

Halogenation. The addition of halogens to an alkyne proceeds in the same manner

as halogen addition to alkenes. The halogen atoms add to an alkyne molecule in a

14
stepwise fashion, leading to the formation of the corresponding alkene, which
undergoes further reaction to a tetrahaloalkane.

Unlike most hydrogenation reactions, it is possible to stop this reaction at the

alkene stage by running it at temperatures slightly below 0°C.

Hydrohalogenation. Hydrogen halides react with alkynes in the same manner as

they do with alkenes.

Both steps in the above addition follow the Markovnikov rule. Thus, the addition of
hydrogen bromide to 1‐butyne gives 2‐bromo‐1‐butene as the major product of the
first step.

The reaction of 2‐bromo‐1‐butene in the second step gives 2,2‐dibromobutane as

the major product.

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 What I Have Learned

1.Alkynes are _____________ hydrocarbons and are called saturated

hydrocarbons
2. Straight-chain alkynes are named according to IUPAC by combining the
___________ for the number of carbon atoms and the suffix ___________.
3. The __________ chain in an alkyne structure contains the longest continuous
chain of carbon atoms.
4. The _____________ in an alkyne are helpful in welding materials like steel and
wire.
5. Alkynes have properties that are essentially the same as those of __________
and ____________.
6. Alkynes have the general formula __________.
7. Addition reactions of alkynes are __________ to those of alkenes.
8. A _____________ is a substance that hastens the rate of ____________, but does
not participate in the actual reaction.
9. In acetylene derived name of alkynes, the __________ groups on both side of
acetylene are named from smaller to larger.
10. When both double and triple bonds are present, numbers as low as possible
are given to double and triple bond even though this may at times give “yne”
a _______ number than “_______”.

What I Can Do

Activity 3. IUPAC Nomenclature of Alkynes

Name the following structures using IUPAC Nomenclature System.
CH2 – CH2 – CH3
l
1) CH3 – C ≡ C – CH2 –CH –CH2 –CH –CH2 –CH3 _____________________
l
Cl

CH2 – CH2 – CH2 – CH3

l
2) CH3 – CH2 – C ≡ C – CH – CH – C ≡ CH ______________________
l
Br

3) F – CH2 – CH2 – CH2 – C ≡ CH _______________________

16
 4) CH3 – CH2 – C ≡ C – CH2 – CH2 - CH3 ________________________

5) CH3 – CH2 – C ≡ C – CH2 – CH3 ________________________

6) _________________________

Additional Activities

There is a plastic polymer called polyvinylidene difluoride (PVDF) that can be used
to sense baby’s breath and thus is used to prevent sudden infant death syndrome
(SIDS). The secret is that this polymer can be specially processed so that it
becomes piezoelectric (produces electric current when it is physically deformed) and
pyroelectric (develops an electrical potential when its temperature changes). When
a PVDF film is placed beside a sleeping baby, it will set off an alarm if the baby
stops breathing.
Make a research and investigate some of the other amazing uses of PVDF.

17
 Assessment

Multiple Choice. Choose the letter of the best answer. Write the chosen letter on a
separate sheet of paper.
1. Alkynes possess physical properties that are essentially the same as those of the
alkanes and alkenes. Which of the following statements is true?
a. boiling point increases with decreasing carbon number
b. alkynes are insoluble in water and benzene
c. alkynes are less dense than water
d. all of the above

2. Alkynes are hydrocarbons that contain triple bonds; which of the following is
the general formula for alkynes?
a. CnH2n c. CnH2n-1
b. CnH2n+2 d. CnH2n-2

3. In naming alkynes using the IUPAC Nomenclature system, the lowest possible
number should be assigned to _________.
a. halogen b. substituent c. double bond d. triple bond

For numbers 4 -7, refer to the following condensed structural

formula:

CH3 – C ≡ C – CH3

4.Which of the following is the acetylene derived name of the given structure?
a. dimethylethyne c. dimethylethylene
b. dimethylethene d. dimethylacetylene

5. Which of the following is the old IUPAC name of the structure?

a. Butene b. Butyne c. But-2-yne d. 2-butyne

6. Which of the following is the preferred IUPAC name of the structure?

a. Butene b. Butyne c. But-2-yne d. 2-butyne

7. Which of the following is the molecular formula of the structure?

a. C4H6 c. CH3C2CH3
b. C2CH3 d.C2 (CH3)2

8. Methylisopropylacetylene is the acetylene derived name of ________.

a. 2-Butyne c. 4-methyl-2-pentyne
b. 2-Pentyne d. 2-methyl-3-pentyne

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 For numbers 9-12, refer to the following structure:

CH3 – CH = CH - C ≡ C – CH3

9.In numbering the parent chain, which of the following should be

assigned the lowest possible number?
a. hydrogen b. single bond c. double bond d. triple bond

10.Which of the following suffixes would be use to designate the double bond?
a. -en b. -ane c. -ene d. -yne

11.Which of the following would be followed in numbering the parent chain?

a. numbering should be from left to right
b. numbering should be from right to left
c. start numbering from the double bond
d. start numbering from the triple bond

12. Which of the following is the IUPAC name of the structure?

a. 2-Hexene-4-yne c. 4-Hexene-2-yne
b. 2-Hexen-4-yne d. 4-Hexen-2-yne

For numbers 13 -15, refer to the following structure:

CH2 – CH3
l
CH3 – C ≡ C – CH2 –CH –CH2 –CH –CH3
l
Br
13. In numbering the parent chain, the lowest possible number should be assigned
to which one of the following?
a. Halogen c. alkyl group
b. Triple bond d. substituents

14. What is the preferred IUPAC name of the above structure?

a. 5-ethyl-7-bromooct-2-yne
b. 7-Bromo-5-ethyloct-2-yne
c. 2-Bromo-4-ethyloct-6-yne
d. 4-ethyl-2-bromooct-6-yne

15. In naming the structure, the substituents should be named first. In the given
structure the substituents are bromine and ethyl, which substituents should be
named first?
a. bromine
b. ethyl

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 Answer Key

10.a
What’s More
9. b Activity 2, Nomenclature of
Alkynes
8. c
7. c
6. c 1. 4-Fluoro-6-ethylnon-2-yne
5. c 2. 1-Octen-5-yne
4. d 3. 5-Bromohept-2-yne
3. b 4. Pent-1-yne, propylacetylene
2. b 5. Hept-3-yne,
1. b ethylpropylacetylene
6. Hex-3-yne, diethylacetylene
know
What I

10.a
9. c
8. c
7. a
6. c
a 15. 5. d
b 14. 4. d
b 13. 3. d
b 12. 2. d
a 11. 1. c

Assessment

20
References
Caret, R.L.,et.al. 1997.Principles and Applications of Inorganic, Organic, &
Biological Chemistry. McGraw-Hill: USA

Vollhardt, Peter, and Neil E. Schore. Organic Chemistry: Structure and Function.
5th Edition. New York: W. H. Freeman & Company, 2007.

Organic Chemistry Laboratory Notes and Worktext. Lyceum Northwestern.

Prepared and compiled by Chemistry Teachers

https://www.reference.com/science/consumer-chemistrya4a24b973cdade4

https://wou.edu/chemistry/course/online_chemistry_textbooks/ch105_consumer
chemistry/

www.britannica.com>science>chemistry

Chem.libretext.org>map: _ organic _Chemistry_(Wade)

http://www.docbrown.info/page06/alkenes1.htm#2.1.1
https://www.sciencedirect.com/topics/chemistry/cycloalkenes

https://www.cliffsnotes.com/study-guides/chemistry/organic-chemistry-
i/alkynes/alkynes-addition-reactions

21
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