GC1 - Q2 - Week 6 Printed December 11 15 2023

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WEEKLY LEARNING ACTIVITY SHEETS

General Chemistry 1 Grade 11, Quarter 2, Week 6
Name: Section:
ORGANIC COMPOUNDS
Lesson 1: Structural Isomers
Learning Competency:
Describe structural isomerism; give examples (STEM_GC11OCIIg-j-89)
Specific Objective:
1. Define structural isomerism;

2. Recognize molecules that are structural isomers of each other given the structural formulas
Time allotment: 2 Hours
Key Concepts
❖ Isomers are different compounds that have the same molecular formula. Isomers are categorized
into structural (or constitutional) isomers and stereoisomers. In this lesson, we will focus only on
structural isomers.
❖ Structural isomers have the same molecular formula but have different connectivity, meaning
that their atoms are connected in different order. The terms structural isomers and constitutional
isomers can be used interchangeably.
SOLVED PROBLEM 1: There are two structural isomers of C4H10. What are these?
Strategy and Answer: (a) C4H10 is an alkane with n=4. A straight-chain alkane with 4 carbon atoms
is butane with the condensed structural formula CH3CH2CH2CH3. Butane has the following dash
structural formula and bond-line structural formula:
Dash formula Bond-line formula
Butane (C4H10)
(b) The other structural isomer of the compound having molecular formula C 4H10 is 2-
methylpropane, a branched alkane. The backbone chain is propane, and the substituent is a methyl
group attached to C2. 2-Methylpropane has the following dash structural formula and bond-line
structural formula:
2-Methylpropane (C4H10)
Author: CRISTOBERT C. AYATON

School/Station: LIANGA NATIONAL COMPREHENSIVE HIGH SCHOOL – LIANGA I DISTRICT
Division: SURIGAO DEL SUR
email address: cristobert.ayaton@deped.gov.ph
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SOLVED PROBLEM 2: What are the two structural isomers of the compound having a molecular
formula C3H7Cl?
Strategy and Answer: (a) If we replace H in place of Cl, we could get C3H8 which is an alkane with
n=3. Therefore, C3H7Cl is an alkyl halide where one H atom is replaced by a Cl atom. A Cl atom
attached to any of the end carbon of propane is a 1° alkyl halide called 1-chloropropane. 1-
Chloropropane has the following structural formula and bond-line structural formula:
1-Chloropropane (C3H7Cl)
(b) The other structural isomer of the compound having a molecular formula C 3 H7Cl is a 2° alkyl
halide called 2-chloropropane. 2-Chloropropane has the following structural formula and bond-line
structural formula:
2-Chloropropane (C3H7Cl)
SOLVED PROBLEM 3: Give the seven structural isomers of the compound having a molecular
formula C4H10 O.
Strategy and Answer:

Alcohols, ethers, aldehydes, and ketones are the classes of organic compounds that contain atoms
of carbon and hydrogen, and at least one atom of oxygen. For C4 H10O, only alcohols and ethers
form structural isomers. The seven structural isomers of C4H10 O are given below:
Alcohols:
Dash formula Bond-line formula Dash formula Bond-line formula
1-Butanol (C4H10O) 2-Butanol (C4H10O)
2-Methyl-1-propanol (C4H10O) 2-Methyl-2-propanol (C4H10O)

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Ethers:
1-Methoxypropane (C4H10O) 2-Methoxypropane (C4H10O)
Ethoxyethane (C4H10O)
SOLVED PROBLEM 4: Propene, CH3 CH═CH2, is an alkene. Write the structure of a constitutional
isomer of propene that is not an alkene. That means it has no double bond.

An alkene with one double bond having n carbon atoms will have the same molecular formula as
a cycloalkane with the same number of carbons. For alkenes and cycloalkanes, the general formula
is CnH2n. Thus, cyclopropane is a constitutional isomer of propene.
Cyclopropane (C3H6) Propene (C3H6)
SOLVED PROBLEM 5: Propose structures of two constitutional isomers of cyclopentene (C 3H8 )

that do not contain a ring.
Cyclopentene (C5H8)
Strategy and Answer: A cycloalkene with n carbon atoms will have the same molecular formula
as an alkyne with the same number of carbon atoms. For alkynes and cycloalkenes, the general
formula is Cn H2n-2 Thus, 1-pentyne and 2-pentyne are constitutional isomers of cyclopentene.
1-pentyne (C5H8) 2-pentyne (C5H8)

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❖ WARNING: Be careful not to draw “false” isomers which are just twisted versions of the original
molecule. For example, the structure below is just the straight-chain version of butane (as in
SOLVED PROBLEM 1.1) rotated about the central carbon-carbon bond.
SOLVED PROBLEM 6: What is the relationship between these two compounds?

They might look lik e different molecules, but they represent the same molecule. There is a
180°- rotation around the bond between C3 and C4 in the heptane backbone chain.
Lesson 2: Simple Reactions of Organic Compounds
Learning Competency:
Describe some simple reactions of organic compounds: combustion of organic fuels, addition,
condensation, and saponification of fats (STEM_GC11OCIIg-j-90)
Specific Objective:
1. Describe and predict the major product of some simple reactions of organic compounds
Time Allotment: 2 Hours
Key Concepts
COMBUSTION OF ORGANIC FUELS
❖ Most alkanes are relatively unreactive primarily because of the strength and lack of polarity of
the C―C and C―H bonds present. At room temperature, for example, alkanes do not react with
acids, bases, and strong oxidizing agents. This low reactivity accounts for the fact that alkanes
were originally called paraffins (Latin: parum affinis, meaning “little affinity”).
❖ Alkanes are not completely inert, however. One of their most commercially important reactions
is combustion in air, which is the basis of their use as fuels.
❖ Generally, many hydrocarbons are used as fuels because their combustion releases very large
amounts of heat energy.
❖ Combustion is the reaction with oxygen to produce heat energy, carbon dioxide, and water. This
reaction occurs, for example, in cylinders of automobiles, in furnaces, and, more gently, with
paraffin candles.
❖ Complete combustion pertains to the complete conversion of carbon to carbon dioxide. Mostly,
combustion reactions are described by complete combustion, especially in theoretical
calculations, i.e. calculations in theoretical yield of carbon dioxide; but in reality, complete
combustion is difficult to achieve.
❖ Incomplete combustion is indicated by the presence of solid elemental carbon and carbon
monoxide in the product, which means that not all the carbon is converted to carbon dioxide. This
happens due to a n insufficient supply of oxygen in the process. Incomplete combustion

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calculations are mostly of industrial applications using material balance such as in the fields of
chemical engineering. In the following examples, however, combustion reactions are assumed
complete.
EXAMPLE 1: Complete combustion of ethane (C2H6 ) proceeds according to this reaction:
𝟐𝑪𝟐𝑯𝟔(𝒈) + 𝟕𝑶𝟐(𝒈) → 𝟒𝑪𝑶𝟐(𝒈) + 𝟔𝑯𝟐𝑶(𝒍)
EXAMPLE 2: Liquefied Petroleum Gas (LPG) is composed of propane, butane, a little methane,
and some other hydrocarbons. Combustion of propane is represented by the reaction:
𝑪𝟑𝑯𝟖(𝒈) + 𝟓𝑶𝟐(𝒈) → 𝟑𝑪𝑶𝟐(𝒈) + 𝟒𝑯𝟐𝑶(𝒍)
EXAMPLE 3: For an internal combustion engine to move a vehicle, it must convert the energy
stored in the fuel into mechanical energy to drive the wheels. Gasoline, one of the most commonly
used fuels, contains a large amount of octane. Combustion of octane proceeds as follows:
𝟐 𝑪𝟖𝑯𝟏𝟖(𝒍) + 𝟐𝟓𝑶𝟐(𝒈) → 𝟏𝟔𝑪𝑶𝟐(𝒈) + 𝟏𝟖𝑯𝟐𝑶(𝒍)
EXAMPLE 4: Ethyne, C2H2, is used in oxyacetylene torches in welding metals. Combustion of

ethyne is represented by the reaction:
𝟐𝑪𝟐𝑯𝟐(𝒈) + 𝟓𝑶𝟐(𝒈) → 𝟒𝑪𝑶𝟐(𝒈) + 𝟐𝑯𝟐𝑶(𝒍)
EXAMPLE 5: Ethanol, C2 H5OH, can be used as a fuel source in an alcohol lamp. Combustion
of ethanol can be written as:
𝑪𝟐𝑯𝟓𝑶𝑯(𝒍) + 𝟑𝑶𝟐(𝒈) → 𝟐𝑪𝑶𝟐(𝒈) + 𝟑𝑯𝟐𝑶(𝒍)
ADDITION REACTIONS OF ALKENES
❖ Addition reaction forms new bonds between new groups and each end of an alkene (as well as
alkyne) forming a single product.
❖ Generally, this type of reaction can be depicted using E for an electrophilic portion of a reagent
and Nu for a nucleophilic portion, as follows.
❖ Electrophiles seek electrons. They are attracted to sites of negative charge and have the property
of being electrophilic.
❖ Nucleophiles are electron donors. They are attracted to sites of positive charge and have the
property of being nucleophilic.
❖ Mechanism of addition reaction: (1) In the protonation (addition of proton, or H+) of an alkene,
the electrophile is the proton (H+) donated by the HX group and the nucleophile is the alkene. The
result is a carbocation (carbon cation) and a halide ion.
Electrophile Nucleophile Carbocation Halide ion
❖ (2) The new electrophile is the carbocation formed from the above reaction, and the new
nucleophile is the halide ion. In this step, the nucleophilic halide ion donates an electron pair
to the carbocation, completing the formation of the product which is haloalkane.

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Electrophile Nucleophile Haloalkane
❖ To promote the reaction, the reaction temperature must be raised t o 500°C, and a catalyst
(such as Pt, Pd, or Ni) is used to assist in rupturing the H―H bond. We write such conditions
over the reaction arrow to indicate they must be present for the reaction to occur. The most widely
used catalysts are finely divided metals on which H 2 is adsorbed.
A. Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s

Rule
➢ Hydrogen halides (HI, HBr, HCl, and HF) add to the double bond of alkenes producing an alkyl
halide.
➢ One way to state Markovnikov’s [pronounced as markofnikof’s] rule is to say that in the
addition of HX to an unsymmetrical alkene, the hydrogen atom adds to the carbon
atom of the double bond that already has the greater number of hydrogen atoms.
➢ The addition of HX to an unsymmetrical alkene could conceivably occur in two ways. However,
one product usually predominates. An unsymmetrical alkene has different groups attached
to each carbon atom in the carbon-carbon double bond of an alkene.
➢ Reactions like the Markovnikov additions of hydrogen halides to alkenes are described as being
regioselective. Regio comes from the Latin word regionem meaning direction. A
regioselective reaction can potentially yield two or more constitutional isomers but that
produces only one (or a predominance of one).
SOLVED PROBLEM 1: What is the main product in the addition of HBr to propene?
Strategy and Answer: The addition of HBr to propene produces 1-bromopropane or 2- 2-

bromopropane. Following Markovnikov’s rule, the hydrogen atom will attach to C1 having the
greater number of hydrogen atoms and the bromine atom will attach to C2. Thus, the main product
is 2-bromopropane. 1-bromopropane will be produced in small amount.
+ H―Br → ( )
Propene Hydrogen bromide 2-Bromopropane 1-Bromopropane
(main product) (little amount)
SOLVED PROBLEM 2: What is the main product when 2-methylpropene reacts with HBr?

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Strategy and Answer: The main product is 2-bromo-2-methylpropane, not 1-bromo-2-
methylpropane. Following Markovnikov’s rule, the hydrogen atom will attach to C1 and the
bromine atom will attach to C2.
+ H―Br → ( )
2-Methylpropene Hydrogen bromide 2-Bromo-2-methylpropane 1-Bromo-2methylpropane
(main product) (little amount)
SOLVED PROBLEM 3: Determine the product when ethene reacts with HCl.
Strategy and Answer: Ethene is a symmetrical alkene. Markovnikov’s rule cannot be applied
and there is only one product which is chloroethane.
+ H―Cl →
Ethene Hydrogen chloride Chloroethane
B. Hydrogenation of Alkenes
➢ Hydrogenation is simply an addition of hydrogen to reduce an alkene to an alkane. One molar

equivalent of hydrogen is required for such a reaction.
➢ The general reaction is one in which the atoms of the hydrogen molecule add to each atom of
the carbon–carbon double bond of the alkene.
➢ The food industry makes use of catalytic hydrogenation to convert liquid vegetable oils to
semisolid fats in making margarine and solid cooking fats. Examine the labels of many
prepared foods and you will find that they contain “partially hydrogenated vegetable oils.”
There are several reasons why foods contain these oils, but one is that partially hydrogenated
vegetable oils have a longer shelf life.
SOLVED PROBLEM 1: What is the product of hydrogenation of ethene, C2H4?
Strategy and Answer: The product of the hydrogenation of ethene is the alkane ethane, C2H6.
+ H―H →
Ethene Hydrogen Ethane
SOLVED PROBLEM 2: What alkane is formed when 2-methyl-1-propene (C4 H8 ) undergoes

hydrogenation reaction?
Strategy and Answer: The alkane formed in the hydrogenation of 2-methyl-1-propene is 2-

methylpropane.

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+ H―H →
2-Methyl-1-propene Hydrogen 2-Methylpropane
SOLVED PROBLEM 3: What is the product of hydrogenation of cyclohexene (C6H10)?
Strategy and Answer: When cyclohexene undergoes a hydrogenation reaction, the product is
cyclohexane.
+ H―H →
Cyclohexene Hydrogen Cyclohexane
ADDITION REACTIONS OF ALKYNES
❖ The addition reaction of alkynes proceeds with the same conditions and catalysts as the
addition reaction of alkenes.
A. Addition of Hydrogen Halides to Alkynes
➢ Alkynes react with one molar equivalent of hydrogen chloride or hydrogen bromide to form
haloalkenes, and with two molar equivalents to form geminal dihalides.
➢ Geminal dihalide has two of the same halogen attached to the same carbon atom.
➢ Both additions are regioselective and follow Markovnikov’s rule:
SOLVED PROBLEM 1: What is the product when 1-hexyne undergoes an addition reaction with
(a) one molar equivalent of hydrogen bromide; an d (b) two molar equivalents of hydrogen bromide?
Strategy and Answer: The carbon-carbon triple bond is located between C1 and C2. C1
contains one hydrogen atom while no hydrogen atom is attached to C2. By Markovnikov’s rule,
the hydrogen atom of hydrogen bromide will attach to C1 and the bromine atom will attach to C2.
(a) 1-Hexyne reacts with one molar equivalent of hydrogen bromide to yield 2-bromo-1- hexene.
(b) The addition of two molar equivalents of hydrogen bromide to 1-hexyne further reduces 2-
bromo-1-hexene to 2,2-dibromohexane.
(a)
+ H―Br →
1-Hexyne Hydrogen bromide 2-Bromo-1-hexene

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(b)
+ 2 H―Br →
1-Hexyne Hydrogen bromide 2,2-Diromohexane
B. Hydrogenation of Alkynes
➢ Hydrogenation is simply an addition of one molar equivalent of hydrogen to reduce an alkyne

to an alkene (or two molar equivalents of hydrogen to reduce an alkyne to an alkane).
➢ The general reaction is one in which the atoms of the hydrogen molecule add to each atom of
the carbon–carbon triple bond of the alkyne.
SOLVED PROBLEM 1: What is the product of hydrogenation of ethyne, C 2H2, with (a) one molar
equivalent of hydrogen; a n d (b) two molar equivalents of hydrogen?
Strategy and Answer: Hydrogenation of ethyne with (a) one molar equivalent of hydrogen yields
ethene and with (b) two molar equivalents yield ethane.
𝐻2 𝐻2
→ →
Ethyne Ethene Ethane
CONDENSATION REACTION: ESTERIFICATION
❖ A condensation reaction is a reaction in which two molecules are joined and a small molecule,
often water, is usually removed during condensation reaction.
❖ Esterification is the formation of an ester by t h e reaction of a carboxylic acid, acid
chloride, or carboxylic acid anhydride with an alcohol or phenol.
Acid-Catalyzed Esterification
➢ Esters can be formed by an acid-catalyzed reaction of a carboxylic acid with an alcohol or

phenol.
Carboxylic acid Alcohol Ester Water
➢ HA is an acid used as catalyst with the application of heat and the double arrow indicates
that the reaction is reversible.
SOLVED PROBLEM 1: What ester is formed in the acid-catalyzed esterification reaction of

ethanoic acid with ethanol?

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Strategy and Answer: Ethanoic acid reacts with ethanol, in the presence of an acid, to produce
an ester ethyl ethanoate and water.
Ethanoic acid Ethanol Ethyl ethanoate Water
SOLVED PROBLEM 2: What is the product in the acid-catalyzed esterification reaction of

benzoic acid and methanol?
Strategy and Answer: When benzoic acid reacts with methanol, the product is methyl benzoate
and water.
Benzoic acid Methanol Methyl benzoate Water
SAPONIFICATION: A BASE-PROMOTED HYDROLYSIS OF ESTERS
❖ Saponification is the reaction of esters with aqueous sodium hydroxide (NaOH) solution to
produce sodium salt of the carboxylic acid and an alcohol. It is a common reaction of esters.
❖ Sapo is a Latin word for soap. This reaction originates from soapmaking and was originally
produced by the hydrolysis of fats.
Ester Sodium hydroxide Sodium carboxylate Alcohol
SOLVED PROBLEM 1: What are the products of the base-promoted hydrolysis of ethyl
butanoate?
Strategy and Answer: Ethyl butanoate reacts with aqueous sodium hydroxide to produce
sodium butanoate and ethanol.
+ NaOH → +
Saponification of Triacylglycerol
➢ Another way to define saponification is that, saponification is the alkaline (basic condition)
hydrolysis of triacylglycerols (or triglycerides), leading to glycerol and a mixture of salts of
long-chain carboxylic acids.

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Triacylglycerol Glycerol Sodium carboxylates

“soap”
SOLVED PROBLEM 2: What are the products in the saponification of a triacylglycerol consisting
palmitic acid, CH3 ―(CH2 )14 ―COOH as the fatty acid component?
Strategy and Answer: Saponification of triacylglycerols with 3 molar equivalents of sodium

hydroxide produces three molar equivalents of sodium salt of long-chain carboxylic acid. Along
with the backbone glycerol as the product, the reaction produces three molar equivalents of sodium
palmitate, CH3―(CH2)14―CO― Na+.
+ 3 NaOH → +
Glyceryl tripalmitate Sodium hydroxide Glycerol Sodium palmitate (Soap)
Lesson 1: Exercises / Activities
Activity 1 – Multiple Choice Questions

What to do: Choose the letter of the correct answer. Consider each pair of structural formulas
that follow and state whether the two formulas represent:
A. the same compound
B. different compounds that are constitutional isomers of each other
C. different compounds that are NOT isomeric
1. 5.
2. 6.
3. 7.
4. 8.

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9. 12.
10. 13.
11. 14.
15.
Activity 2
What to do: Answer as directed.
1. Write the balanced chemical equation for the combustion reaction of butane, C4H10.
2. What is the main product in the addition of HBr to 3-methyl-1-pentene? Write the chemical
equation using structural formulas of the reactants and the product.
3. What is the product of the addition of two molar equivalents of HCl to 3-methyl-1-pentyne?
Write the chemical equation using structural formulas of the reactants and the product.
4. What is the product of the hydrogenation of 2,3-dimethyl-1-heptyne with (a) one molar
equivalent of hydrogen, and (b) two molar equivalents of hydrogen? Write the chemical equation
using structural formulas of the reactants and the product.
References for learners:

Brown, T. L., LeMay, H. E., Bursten, B. E., Murphy, C. J., & Woodward, P. M.
(2012). Chemistry: The Central Science. (13th ed.) Pearson Prentice Hall.
Patalinghug, Wyona C., Vic Marie I. Camacho, Fortunato B. Sevilla III, and Maria Cristina
D. Singson. 2016. Teaching Guide for Senior High School General Chemistry 1. Quezon City:
Commission on Higher Education.
Solomons, G T.W., Fhryle, C. B., Synder, S. A. 2016. Organic Chemistry. (12th ed). Wiley.


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WEEKLY LEARNING ACTIVITY SHEETS

Lesson 1: Structural Isomers

Describe structural isomerism; give examples (STEM_GC11OCIIg-j-89)

1. Define structural isomerism;

Time allotment: 2 Hours

Dash formula Bond-line formula

Dash formula Bond-line formula

Author: CRISTOBERT C. AYATON

Dash formula Bond-line formula

Dash formula Bond-line formula

Strategy and Answer:

Dash formula Bond-line formula Dash formula Bond-line formula

1-Butanol (C4H10O) 2-Butanol (C4H10O)

Dash formula Bond-line formula Dash formula Bond-line formula

2-Methyl-1-propanol (C4H10O) 2-Methyl-2-propanol (C4H10O)

Author: CRISTOBERT C. AYATON

Dash formula Bond-line formula Dash formula Bond-line formula

1-Methoxypropane (C4H10O) 2-Methoxypropane (C4H10O)

Dash formula Bond-line formula

Strategy and Answer:

Dash formula Bond-line formula Dash formula Bond-line formula

Cyclopropane (C3H6) Propene (C3H6)

SOLVED PROBLEM 5: Propose structures of two constitutional isomers of cyclopentene (C 3H8 )

Dash formula Bond-line formula

Dash formula Bond-line formula Dash formula Bond-line formula

1-pentyne (C5H8) 2-pentyne (C5H8)

Author: CRISTOBERT C. AYATON

SOLVED PROBLEM 6: What is the relationship between these two compounds?

Strategy and Answer:

Lesson 2: Simple Reactions of Organic Compounds

Time Allotment: 2 Hours

COMBUSTION OF ORGANIC FUELS

Author: CRISTOBERT C. AYATON

EXAMPLE 1: Complete combustion of ethane (C2H6 ) proceeds according to this reaction:

𝟐𝑪𝟐𝑯𝟔(𝒈) + 𝟕𝑶𝟐(𝒈) → 𝟒𝑪𝑶𝟐(𝒈) + 𝟔𝑯𝟐𝑶(𝒍)

𝑪𝟑𝑯𝟖(𝒈) + 𝟓𝑶𝟐(𝒈) → 𝟑𝑪𝑶𝟐(𝒈) + 𝟒𝑯𝟐𝑶(𝒍)

EXAMPLE 4: Ethyne, C2H2, is used in oxyacetylene torches in welding metals. Combustion of

𝟐𝑪𝟐𝑯𝟐(𝒈) + 𝟓𝑶𝟐(𝒈) → 𝟒𝑪𝑶𝟐(𝒈) + 𝟐𝑯𝟐𝑶(𝒍)

𝑪𝟐𝑯𝟓𝑶𝑯(𝒍) + 𝟑𝑶𝟐(𝒈) → 𝟐𝑪𝑶𝟐(𝒈) + 𝟑𝑯𝟐𝑶(𝒍)

ADDITION REACTIONS OF ALKENES

Electrophile Nucleophile Carbocation Halide ion

Author: CRISTOBERT C. AYATON

Electrophile Nucleophile Haloalkane

A. Electrophilic Addition of Hydrogen Halides to Alkenes: Mechanism and Markovnikov’s

Strategy and Answer: The addition of HBr to propene produces 1-bromopropane or 2- 2-

Author: CRISTOBERT C. AYATON

➢ Hydrogenation is simply an addition of hydrogen to reduce an alkene to an alkane. One molar

SOLVED PROBLEM 1: What is the product of hydrogenation of ethene, C2H4?

Ethene Hydrogen Ethane

SOLVED PROBLEM 2: What alkane is formed when 2-methyl-1-propene (C4 H8 ) undergoes

Strategy and Answer: The alkane formed in the hydrogenation of 2-methyl-1-propene is 2-

Author: CRISTOBERT C. AYATON

2-Methyl-1-propene Hydrogen 2-Methylpropane

SOLVED PROBLEM 3: What is the product of hydrogenation of cyclohexene (C6H10)?

Cyclohexene Hydrogen Cyclohexane

ADDITION REACTIONS OF ALKYNES

A. Addition of Hydrogen Halides to Alkynes

1-Hexyne Hydrogen bromide 2-Bromo-1-hexene

Author: CRISTOBERT C. AYATON

1-Hexyne Hydrogen bromide 2,2-Diromohexane

➢ Hydrogenation is simply an addition of one molar equivalent of hydrogen to reduce an alkyne

Ethyne Ethene Ethane