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General Chemistry 1 2nd Quarter
General Chemistry 1 2nd Quarter
General Chemistry 1 2nd Quarter
Learning Objectives:
Key Concepts
A. Quantum Numbers:
Determine the home address of your friends or relatives using the format of house number,
street, purok name, barangay, municipality and zip code. How many of your
friends/relatives live on the same street? How many have the same house number?
Just as there are no two houses that have the same address (they could have the same
purok but they are of different house number/street), no two electrons in an atom have the
same set of four quantum numbers. Quantum numbers tell where an electron is located
around the nucleus of an atom. It is kind of like the address of electrons.
There are four quantum numbers, three of which, the principal quantum number (n), the
angular momentum quantum number (ℓ), and the magnetic quantum number (ml)
describe the atomic orbitals that is a region of space where you can most probably find the
electron. A fourth quantum number, the spin quantum number (ms) completes the
description (spin orientation) of the electrons in the atoms.
The Principal Quantum Number (n)
a. Determines the energy of an orbital; describes the
energy level an electron is placed in
b. Determines the orbital size
c. Is associated with the average distance of the electron
from the nucleus in a particular orbital; the larger the
value of n, the farther the average distance of the
electron from the nucleus
d. n can have the values 1, 2, 3, …
Image Source:
(a-c) Wyona C Patalinghug et al., Teaching Guide for Senior High School General Chemistry 1 (Diliman, Quezon City,
Philippines: Commission on Higher Education, 2016), 171-172.
The four quantum numbers compose the numbers that describe where an electron is
located around the nucleus of an atom. It is kind of like the electron's address. The
quantum numbers shall be in the order: energy level (n), sub-level or orbital type (ℓ), the
Image source: Kevin Boudreaux, “Quantum Numbers, Atomic Orbitals, and Electron Configurations,”
2020, https://www.angelo.edu/faculty/kboudrea/index.htm.
B. Orbital Diagrams:
Writing the quantum numbers of electrons in set notation like (3,1,-1,-1⁄2) is time
consuming and difficult to compare so an abbreviated form was developed. With electron
configuration, the first two quantum numbers, n and ℓ, are listed; it also shows how many
electrons exist in each orbital. Many times it is needed to see all the quantum numbers in
an electron configuration, this is the purpose of the orbital diagram. Orbital diagrams
pictorially describe the electrons in an atom. In addition to listing the principal quantum
number, n, and the subshell, ℓ, (which can also be seen in the electron configuration) the
orbital diagram shows all the different orientations and the spin of every electron. Orbital
diagrams illustrate the number of subshells using lines or boxes for electrons (one box/line
for s-orbital, three for p-orbitals, five for d-orbitals, and 7 for f-orbitals). In each box,
electron spin is noted by using arrows; up arrows indicate 1⁄2 spin and down arrows mean
–1⁄2 spin.
- Based on figure f, examine why the first orbital diagram below violates Aufbau
Principle.
- The Aufbau Principle is not a universal rule; not all atoms obey it. Around ten
transition metals violate the Aufbau Principle (Cr, Cu, Nb, Mo, Ru, Rh, Pd, Ag, Pt,
and Au). In each element, the d orbital had an extra electron from the s orbital,
except in Pd where two electrons are consumed by the d orbital. In lanthanides
and actinides, ten elements go against the Aufbau Principle (La, Ce, Gd, Ac, Th,
Pa, U, Np, Cm, and Lr). In the said elements, the d orbital takes an electron from
the f orbital; Th and Lr are special cases. In Th, 6d takes both electrons from 5f
while in Lr 6d is replaced by 7p.
b. Pauli Exclusion Principle states that no two electrons in an atom can have the
same four quantum numbers. This is why each orbital only has two electrons, one
with up-spin (1⁄2) and one with down-spin (–1⁄2).
c. Hund’s Rule states that same-energy orbitals, those which differ only in their
orientation, are filled with electrons that have the same spin before the second
electron is added to any of the orbitals.
Reflection
Give practical applications of quantum numbers/orbital diagrams/magnetic property in
real life. Write your responses on a separate sheet of paper. Be guided with the following rubrics:
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Answer Key
Activity No. 1:
Is it Quantum
Condensed Draw the orbital diagram for the
paramagnetic Number of the
Element Electron subshell in the highest energy level
or Last Electron
Configuration containing the last electron
diamagnetic? n ℓ ml ms
Na [Ne]3s1 ↑ paramagnetic* 3 0 0 1/2
Ca [Ar]4s2 ↑↓ diamagnetic* 4 0 0 -1/2
*ground state
Learning Objective:
Specific Objectives:
Key Concepts
- Ions are formed when there is unequal number of protons and electrons. When a neutral
atom loses electron, it becomes a cation. If an atom gains an electron it will become an
anion.
- Ionization Energy (IE) is the amount of energy required to remove an electron. Ionization
energy increases from left to right across a period. It decreases from top to bottom in a
group. This means that elements under Group 1A have the lowest ionization energy in every
period while elements under Group 8A have the highest ionization energy in every period.
Elements with low ionization energy such as metals have the tendency to give up electrons
easily forming cations with a positive (+) charge.
- For a metal, the total number of dots is the maximum number of electrons an atom loses
to form a cation with a positive (+) charge.
1s22s1 1s2
[He] 2s1 [He]
- Generally, ionization energy measures the energy change when an atom loses an
electron while electron affinity measures the energy change when an atom gains an
electron.
- For a nonmetal, the number of unpaired dots is the number of electrons that become
paired either through electron gain or through electron sharing to form an anion with a
negative (-) charge.
1s22s22p3 1s22s22p6
[He] 2s22p3 [Ne]
- Atoms form bonds with other atoms in order to have a stable electronic configuration.
This will happen if atoms are isoelectronic with its nearest noble gas or having 8
electrons in its outermost shell, except for He which is stable with 2 valence electrons.
Nitrogen 5A 5 Nonmetal 3
Cesium
Barium
Phosphorus
Sulfur
Bromine
Guide Questions
1. Which type of elements will likely to form a cation? Anion?
2. How are cations and anions formed?
3. What did you notice about the charge of the ion?
What to do: Read the text below and identify the important ions present in our body.
Complete the table below by identifying of the ions, group number and valence electrons. In
the last column, draw the structures of these ions.
Ions are important in our body for their physiological and metabolic
functions. We can obtain these ions from the food that we eat. Salt and cheese
provide sodium ions which are important in regulating body fluids. Bananas,
orange juice, milk and potatoes are rich in potassium ions which also regulates
body fluids and cellular functions. Milk, yogurt, cheese, greens and spinach are
great sources of calcium ion which is a major cation present in our bone. These
ions should be present in balanced amount in order maintain stable internal
condition.
Group Valence
Ions in the Body Lewis Structure
Number Electrons
1.
2.
3.
Reflection
RUBRICS
3 2 1 0
High level of Moderate level of Low level of science No explanation at
science concept science concept concept all.
understanding is understanding is understanding is
apparent in the apparent in the apparent
explanation with explanation with with
no misconceptions. minimal misconceptions.
misconceptions.
Agnew, Marisa Alviar, and Henry Agnew. 2020. Chemistry LibreTexts. August 11. Accessed
October 29, 2020.
https://chem.libretexts.org/Courses/College_of_Marin/CHEM_114%3A_Introductory_
Chemistry/10%3A_Chemical_Bonding/10.03%3A_Lewis_Structures_of_Ionic_Compou
nds-_Electrons_Transferred.
Bayquen, Aristea V., and Gardee T. Peña. 2016. General Chemistry 1. Quezon City: Phoenix
Publishing House, Inc.
Brown, Theodore L., H. Eugene Lemay, Bruce E. Bursten, Catherine J. Murphy, Patrick M.
Woodward, and Mathew W. Stoltzfus. Chemistry the Central Science. 14th ed. New
York: Pearson, 2018.
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.
Zumdahl, Steven S., and Susan A. Zumdahl. 2014. Chemistry. Belmont, CA: Brooks/Cole,
Cengage Learning.
Answer Key
Nitrogen 5A 5 Nonmetal 3
Phosphorus 5A 5 Nonmetal 3
Sulfur 6A 6 Nonmetal 2
Bromine 7A 7 Nonmetal 1
1. Metals tend to lose electrons forming cations while nonmetals tend to gain electrons
forming into anions.
2. Cation is formed when a neutral atom loses one or more electrons.
Anion is formed when a neutral atom gains one or more electrons.
3. The charge of the ion corresponds to the number of electrons lost or gained.
Group Valence
Ions in the Body Lewis Structure
Number Electrons
1. Sodium 1A 1 Na+
2. Potassium 1A 1 K+
3. Calcium 2A 2 Ca2+
COVALENT COMPOUNDS
Learning Objective:
Specific Objectives:
Key Concepts
- Covalent compounds are formed when a pair of electrons are shared between
nonmetals.
- Octet Rule states that when atoms gain, lose, or share electrons to form bonds
with other atoms they tend to achieve the electron configuration of the noble gas
nearest to them with eight valence electrons.
- There are three types of covalent bonds namely single bond, double bond and triple
bond.
- Bonding electrons are electrons shared between atoms.
- Nonbonding electrons are electrons that does not participating in bonding or not
shared between other atoms.
- Lewis structure shows how electrons are arranged in an atom.
- Steps in drawing the Lewis structures of compounds:
Step 1. Determine the valence electrons of every atom involved.
Step 2. Get the sum of the all the valence electrons of atoms.
Step 3. Use a pair of electrons to form a single bond between atoms.
Step 4. Arrange the remaining electrons around the atom to satisfy the octet rule
except for Hydrogen which is stable with 2 valence electrons.
Step 2. Get the sum of the all the valence electrons of atoms.
Total valence electrons:
Fluorine = 7 valence electrons x 2 atoms
= 14 electrons
Step 4. Arrange the remaining electrons around the atom to satisfy the octet rule
except for Hydrogen which is stable with 2 valence electrons.
Lone pair
Bond pair
Check: Count the number of valence electrons whether each atom of Fluorine satisfies the
octet rule.
Fluorine = bonding electrons + nonbonding electrons
Fluorine = (1 x 2 e-) + 6 e-
Fluorine = 2 e- + 6 e-
Fluorine = 8 e-
Check: Count the number of valence electrons whether each atom satisfies the octet rule.
Step 4.
Oxygen (1) = 7 e-
Carbon = 6 e-
Oxygen (2) = 7 e-
Step 3.
10 electrons – 2 electrons = 8 electrons
Check: Count the number of valence electrons whether each atom satisfies the octet rule.
Check: Count the number of valence electrons whether each atom satisfies the octet rule.
d. Arrange the remaining electrons around the atom to satisfy the octet rule.
or
Check: Count the number of valence electrons whether each atom satisfies the octet rule.
1 2 3
- Based from the Lewis structure of ozone above, there are two possible Lewis structures.
However, experimental results show that the bond length of ozone is between that of a
single bond and a double bond. This implies that we cannot use the two Lewis structures
above to represent ozone.
- In order to represent the Lewis structure of ozone accurately, a double-sided arrow is
placed in between the structures of ozone. These structures of ozone are called resonance
structures.
↔
-
- A resonance structure is one of two or more Lewis structures for a molecule that cannot
be represented accurately by only one Lewis structure.
- What is the correct representation for ozone?
Answer: The two resonance structures shown with the double arrow.
and
3. Molecules with more than an octet of valence electrons.
Elements along the 3rd period and beyond have 3d orbitals that can participate in
chemical bonding. Hence, it is possible for the central atoms from 3rd period and
beyond to have expanded. Sulfur hexafluoride (SF6) and phosphorus pentachloride
(PCl5) are examples of compound having more than 8 electrons around the central
atom.
SF6
PCl5
What to do:
Draw the Lewis structure of the following covalent compounds.
1. O2
2. CH4
3. NCl3
4. HCN
5. HBr
What to do:
Write the chemical formula of the following molecular compounds.
1. Dichlorine hexoxide
2. Silicon dioxide
3. Dinitrogen trioxide
4. Sulfur pentoxide
5. Hydrogen sulfide
What to do:
1. Look for at least two examples of covalent compounds found in the
environment.
2. Write a brief explanation about the covalent compounds.
3. Write the chemical formula and name of the chemical compound.
4. Draw the structure of the compound.
Sample:
Assessment
1. What type of bond is formed when electrons are shared between atoms?
A. covalent bond.
B. chemical bond
C. ionic bond
D. metallic bond
3. Which of the following elements will have 5 electrons in its Lewis dot structure?
A. Boron
B. Carbon
C. Nitrogen
D. Sulfur
6. What is the chemical name of a compound which has two atoms of nitrogen and
five atoms of oxygen?
A. dinitrogen pentoxide
B. nitrogen dioxide
C. nitrogen monoxide
D. trinitrogen trioxide
A. C.
B. D.
9. Which of the following compounds have fewer than 8 valence electrons around
the central atom?
A. C2H6
B. AsF5
C. CFCl3
D. BF3
10. Which of the following is the correct Lewis structure for methanal, CH2O?
A. C.
B. D.
RUBRICS
3 2 1 0
High level of Moderate level of Low level of science No explanation at
science concept science concept concept all.
understanding is understanding is understanding is
apparent in the apparent in the apparent
explanation with explanation with with
no misconceptions. minimal misconceptions.
misconceptions.
Bayquen, Aristea V., and Gardee T. Peña. 2016. General Chemistry 1. Quezon City:
Phoenix Publishing House, Inc.
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.
Answer Key
Activity 1 Assessment
1. A
1.
2. D
3. C
4. C
2. 5. D
6. A
7. A
3. 8. B
4. 9. D
10. A
5.
Activity 2
1. Cl2O6
2. SiO2
3. N2O3
4. SO5
5. H 2S
Learning Objective:
Specific Objectives:
After the lesson, the students will be able to:
1. determine whether of a bond is ionic, nonpolar or polar covalent based on the
electronegativity difference
2. Apply the Valence Shell Electron Pair Repulsion Theory to predict the geometry of
molecules.
3. Predict the polarity of molecule
Key Concepts
Molecular Geometry
Trigonal Trigonal
3 3 0 120° BF3
Planar Planar
Trigonal
3 2 1 <120° Bent NO2-
Planar
Trigonal
4 Tetrahedral 3 1 <109.5° NH3
Pyramidal
90°
Trigonal (axial) Trigonal
5 5 0 PCl5
Bipyramidal 120° Bipyramidal
(equatorial)
90°
Trigonal (axial)
5 Bipyramidal 4 1 120° Seesaw SF4
(equatorial)
Trigonal
<90° (axial)
5 Bipyramidal 3 2 T-shaped ClF3
Trigonal
180°
5 Bipyramidal 2 3 Linear XeF2
Octahedral 90°
6 6 0 Octahedral SF6
Table 1. Molecular Shapes for Central Atom with Two, Three and Four Bonded Atoms
Image source:
Theodore L. Brown et al., Chemistry the Central Science, 14th ed. (New York: Pearson, 2018), 389-392.
Example: Predict the molecular geometry of BeCl2.
- The table above will guide you how to identify the electron group geometry as well as
the molecular geometry of compounds. Note that, if there are no lone pairs around the
central atom the electron group geometry is the same with its molecular geometry.
Bond Polarity
- Covalent bonds may be classified into nonpolar or polar covalent bonds depending on
the electronegativity difference between atoms.
- Electronegativity refers to the ability of an atom to draw or attract the electrons of
other atoms toward itself. Elements with greater electronegativity value such as
Fluorine has a higher tendency to attract the electrons of other atoms.
- In a polar covalent bond, the shared electrons are more attracted to the more
electronegative atom making it partially negative (ẟ-) while the other end becomes
partially positive (ẟ+) due to the lack of electrons in an atom. Polar covalent bond that
has a separation of charges is called a dipole. An arrow ( ) is used to represent
dipole where the arrow head is pointed towards the more electronegative atom.
- In a nonpolar covalent bond, electrons are shared equally between atoms. The
electronegativity difference ranges from 0.0 to 0.4.
Electronegativity
Type of Bond Reason
Difference
Ca─Cl
3.0-1.0=2.0 Ionic bond Greater than 1.8
bond in CaCl2
C─S Nonpolar Between 0 and
2.5-2.5=0.0
bond in CS2 covalent bond 0.4
- If the electronegativity difference is greater than 1.8, electrons are not shared but
transferred from one atom to another which results to formation of an ionic bond.
- Consider the atoms of hydrogen and chlorine. Hydrogen atom has an electronegativity
value of 2.1 and chlorine atom has 3.0. These values imply that the electrons of
hydrogen are drawn towards chlorine atom which results to a partially negative
chlorine and partially positive hydrogen.
H─Cl
ẟ+ ẟ-
- Between carbon and sulfur, both atoms have the same electronegativity value of 2.5.
This means that the electrons are shared equally between carbon and sulfur making
the bond nonpolar.
ẟ+ ẟ+
Consider the bent shape of water. The individual dipoles are directed towards oxygen,
therefore, they do not cancel each other which explains that water molecule is polar.
The net dipole moment of oxygen is upward.
ẟ- ẟ+ ẟ-
The bonds between carbon and oxygen are both polar. However, these bonds are
directed in opposite direction which cancels out resulting to a net dipole moment of 0.
- The polarity of substances will help us in determining its solubility in different
solvents. Solubility of substances follows the general rule “like dissolves like”. Polar
solute dissolves in a polar solvent. Nonpolar solute dissolves in a nonpolar solvent
2. NCl3
3. CH4
4. PCl5
Image source:
Karen C. Timberlake, Chemistry, an Introduction to General, Organic, and
Biological Chemistry, Twelfth Edition (Upper Saddle River: Prentice Hall, 2015),
189.
What to do: Identify the type of bond between each pair of atoms. Use the electronegativity
values provided in Figure 3.
Electronegativity
Type of Bond
Difference
C─O
3.5-2.5=1.0 Polar Covalent Bond
bond in CO
1. H─H
bond in H2
2. Br─Cl
bond in BrCl3
3. H─Br
bond in HBr
4. As─Cl
bond in AsCl5
5. P─Br
bond in PBr5
What to do: Determine the molecular geometry and polarity of the following molecules.
Lewis Molecular
Polarity
Structure Geometry
1.
2.
3.
4.
5.
Assessment
A. 1
B. 2
C. 3
D. 4
3. Which statement best explains why CH2O is more polar than CCl2O?
CCl2O CH2O
A. C.
B. D.
A. H─F C. S─Cl
B. O─S D. B─H
Reflection
RUBRICS
3 2 1 0
High level of Moderate level of Low level of science No explanation at
science concept science concept concept all.
understanding is understanding is understanding is
apparent in the apparent in the apparent
explanation with explanation with with
no misconceptions. minimal misconceptions.
misconceptions.
Bayquen, Aristea V., and Gardee T. Peña. 2016. General Chemistry 1. Quezon City: Phoenix
Publishing House, Inc.
Brown, Theodore L., H. Eugene Lemay, Bruce E. Bursten, Catherine J. Murphy, Patrick M.
Woodward, and Mathew W. Stoltzfus. Chemistry the Central Science. 14th ed. New
York: Pearson, 2018.
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.
Activity 1.
Electron-
Lewis Electron Bonded Lone Bond Molecular
Compound Group
Structure Groups Atoms Pairs Angle Geometry
Geometry
BeCl2 2 Linear 2 0 180° Linear
1. HCN 2 Linear 2 0 180° Linear
Trigonal
2. NCl3 4 Tetrahedral 3 1 109.5°
pyramidal
Activity 2.
Electronegativity
Type of Bond
Difference
1. H─H
2.1-2.1 = 0.0 Nonpolar covalent bond
bond in H2
2. Br─Cl
3.0-2.8 = 0.2 Nonpolar covalent bond
bond in BrCl3
3. H─Br
2.8-2.1 = 0.7 Polar covalent bond
bond in HBr
4. As─Cl
3.0-2.0 = 1.0 Polar covalent bond
bond in AsCl5
5. P─Br
2.8-2.1 = 0.7 Polar covalent bond
bond in PBr5
Activity 3.
Lewis Molecular
Polarity
Structure Geometry
1. Linear Polar
2. Linear Polar
Tetrahedral Nonpolar
5.
1. C
2. B
3. A
4. A
5. A
6. D
7. A
8. D
9. C
10. C
ORGANIC COMPOUNDS
Learning Competency:
Specific Objectives:
1. Describe the major functional groups in organic chemistry and name organic compounds;
2. Recognize from the structural formula which class of organic compounds a certain molecule
belongs; and
3. Identify all the functional groups present in a molecule given its structural formula.
Key Concepts
Organic compounds are compounds containing one or more atoms of carbon EXCEPT oxides
of carbon (e.g., CO and CO2); carbides (e.g., CaC2, commonly known as “kalburo”); cyanides
(e.g., NaCN); carbonates (e.g., CaCO3); hydrogen carbonates or bicarbonates (e.g., NaHCO3); and
allotropes of carbon (e.g., diamond, graphite, graphene, and fullerenes such as
buckminsterfullerene, or C60).
Carbon can form four covalent bonds. It forms strong bonds with a variety of elements,
especially H, O, N, and the halogens. Carbon also has an exceptional ability to bond to another
carbon atom/s forming a variety of molecules made up of chains (straight/unbranched,
branched, or cyclic) of carbon atoms in endless arrays.
Molecular formula is a chemical formula that indicates the actual numbers of atoms present
in a molecule. For example, the molecular formula CH4 for methane tells us that methane has
one carbon atom and four hydrogen atoms.
Structural formula displays the atoms of the molecule in the order they are bonded. It also
depicts how the atoms are bonded to one another. There are four types of structural formulas:
electron-dot formula, dash formula, condensed formula, and bond-line formula or skeletal formula.
Examples of these four types are shown below using 1-propanol as an example.
Although electron-dot formulas account explicitly for all the valence electrons in a molecule,
they are tedious and time-consuming to write. Dash, condensed, and bond-line formulas are
therefore used more often.
Dash formulas have lines that show bonding electron pairs and include elemental symbols for
all the atoms in a molecule.
If we look at Fig.1b-d, we find that the chain of atoms in those formulas is “straight.” Fig.1a
and Fig.1e correspond more accurately to the actual shape of the molecule where the chain
of atoms is “not at all straight.” A better description is unbranched.
Atoms joined by single bonds can rotate relatively freely with respect to one another.
The relatively free rotation of single bonds mean that the chain of atoms can assume a variety
of arrangements. Consider the dash formulas of 1-propanol.
Consider the compound called 2-propanol (or isopropyl alcohol), whose dash formula can be
written in a variety of ways:
In condensed formulas, all hydrogens that are attached to a particular carbon are usually
written immediately after that carbon. In fully condensed structural formulas, all of the atoms
that are attached to a particular carbon are usually written immediately after that carbon,
listing hydrogens first. Consider 2-chlorobutane as an example.
The condensed formulas for 2-propanol can be written in four different ways:
The most common type of structural formula used in organic chemistry, and the fastest to
draw, is the bond-line formula. Another term for bond-line formula is skeletal formula.
Bond-line formula lacks symbols that are explicitly shown in the dash and condensed
formulas. It allows us to more quickly interpret molecular connectivity and compare one
molecular formula with another.
In drawing bond-line formulas, we apply the following rules:
Each bend in a line and terminus of a line represents a carbon atom, unless another group
is shown explicitly.
No Cs are written for carbon atoms, except optionally for CH 3 groups at the end of a chain
or branch.
No Hs are shown for hydrogen atoms, unless they are needed to give a three-dimensional
perspective.
The number of hydrogen atoms bonded to each carbon is inferred by assuming that as
many hydrogen atoms are present as needed to fill the valence shell of the carbon, unless
a charge is indicated.
When an atom other than carbon or hydrogen is present, the symbol for that element is
written at the appropriate location (i.e., in place of a bend or at the terminus of the line
leading to the atom).
Hydrogen atoms bonded to atoms other than carbon (e.g., oxygen or nitrogen) are written
explicitly such as the H in OH.
Bond-line formulas are easy to draw for molecules with multiple bonds and for cyclic
molecules, as well. The following are some examples.
Strategy and Answer: We outline the carbon skeleton including the OH group as follows:
Hydrocarbons are compounds that contain only carbon and hydrogen atoms. Hydrocarbons
are further classified into aliphatic hydrocarbons (those that do not contain benzene ring) and
aromatic hydrocarbons (those that contain benzene ring). Names of hydrocarbons end in -ane,
-ene, or -yne which then tell us what kinds of carbon–carbon bonds are present. The name of
the parent compound is determined by the number of carbon atoms in the longest chain.
A. Alkanes contain only carbon-carbon single bond (C―C), and this is indicated in the family
name and in names for specific compounds by an -ane ending.
Alkanes, except cycloalkanes, have the general formula CnH2n+2 where n=1, 2, 3, ….
They are also known as saturated hydrocarbons because these compounds contain the
maximum number of hydrogen atoms that can bond to carbon atoms present; that is, they
are saturated with hydrogen atoms.
Alkyl groups are the groups that would be obtained by removing a hydrogen atom from an
alkane. These groups are identified for the purpose of naming compounds. These alkyl groups
have names that end in -yl.
When the alkane is unbranched, and the hydrogen atom that is removed is a terminal
hydrogen atom, the names are straight forward. Examples of unbranched alkyl groups are
methyl, ethyl, propyl and butyl.
Methyl group can be derived from methane by removing one H atom. Ethyl group can be
derived from ethane after the removal of one H atom attached from any of the two C atoms.
For alkanes with more than two carbon atoms, more than one alkyl groups can be derived.
Two alkyl groups can be derived from propane. (1) Removal of one terminal H atom forms an
unbranched alkyl called propyl group; (2) removal of one H atom from the middle C atom
forms a branched alkyl called 1-methylethyl (systematic name) or isopropyl group (common
name).
Three-carbon groups
There are four alkyl groups can be derived from an alkane with 4 carbon atoms.
Four-carbon groups
There is one of the seven five-carbon groups with an IUPAC approved common name: the 2,2-
dimethylpropyl group, commonly called the neopentyl group.
Generally, the symbol R is used to represent any alkyl group. For example, R might be
methyl, ethyl, propyl, isopropyl, butyl, tert-butyl, etc.
Alkyl halides or haloalkanes are compounds in which halogens (fluorine, chlorine, bromine,
or iodine) replaces a hydrogen atom of an alkane.
Alkyl halides or haloalkanes have the general formula RX where X = F, Cl, Br, or I. In naming
compounds with halogen substituents, we use fluoro, chloro, bromo, and iodo.
Alkyl halides are classified as being primary (1°), secondary (2°), or tertiary (3°). (We do not
say first degree, second degree, or third degree, but rather we say primary, secondary, or
tertiary.) This classification is based on the carbon atom to which the halogen is
directly attached.
A. 1° Alkyl halide – If the carbon atom that bears the halogen is directly attached to only one
other carbon, the carbon atom is said to be a primary carbon and the alkyl halide is classified
as a primary alkyl halide.
B. 2° Alkyl halide – If the carbon that bears the halogen is itself directly attached to two
other carbon atoms, then the carbon is a secondary carbon and the alkyl halide is a
secondary alkyl halide.
C. 3° Alkyl halide - If the carbon that bears the halogen is directly attached to three other
carbon atoms, then the carbon is a tertiary carbon and the alkyl halide is a tertiary alkyl
halide.
Nomenclature of Alkanes
Today, chemists use a systematic nomenclature developed and updated by the International
Union of Pure and Applied Chemistry (IUPAC). Underlying the IUPAC system is a fundamental
principle: each different compound should have a different and unambiguous name.
In IUPAC substitutive nomenclature a name may have as many as four features: locants,
prefixes, parent compound, and suffixes. Consider the following example:
The locant 4- tells that the substituent methyl group, named as a prefix, is attached to the
parent compound at C4. The parent compound contains six carbon atoms and no multiple
bonds, hence the parent name is hexane, and it is an alcohol; therefore it has the suffix -ol.
The locant 1- tells that C1 bears the hydroxyl group. In general, numbering of the chain
always begins at the end nearer the group named as a suffix.
The locant for a suffix (whether it is for an alcohol or another functional group) may be placed
before the parent name as in the above example or, according to a 1993 IUPAC revision of
the rules, immediately before the suffix. Both methods are IUPAC approved. Therefore, the
above compound could also be named 4-methylhexan-1-ol.
Naming unbranched alkane is very straight forward using the prefix that corresponds to the
number of carbon atoms and an ending -ane. The names for the first twenty unbranched
alkanes are listed in Table 2.
1. Locate the longest continuous chain of carbon atoms; this chain determines the parent
name for the alkane. We designate the following compound, for example, as a hexane because
the longest continuous chain contains six carbon atoms:
The longest continuous chain may not always be obvious from the way the formula is written.
Notice, for example, that the following alkane is designated as a heptane because the longest
chain contains seven carbon atoms:
2. Number the longest chain beginning with the end of the chain nearer the substituent.
Applying this rule, we number the two alkanes that we illustrated previously in the following
way:
3. Use the numbers obtained by application of rule 2 to designate the location of the
substituent group. The parent name is placed last, and the substituent group, preceded by the
number designating its location on the chain, is placed first. Numbers are separated from words
by a hyphen. Our two examples are 2-methylhexane and 3-methylheptane, respectively:
4. When two or more substituents are present, give each substituent a number
corresponding to its location on the longest chain. For example, we designate the following
compound as 4-ethyl-2-methylhexane:
The substituent groups should be listed alphabetically (i.e., ethyl before methyl). In deciding on
alphabetical order, disregard multiplying prefixes such as “di” and “tri.”
5. When two substituents are present on the same carbon atom, use that number twice:
6. When two or more substituents are identical, indicate this by the use of the prefixes
di-, tri-, tetra-, and so on. Then make certain that each and every substituent has a number.
Commas are used to separate numbers from each other:
Application of these six rules allows us to name most of the alkanes that we shall encounter.
Two other rules, however, may be required occasionally:
7. When two chains of equal length compete for selection as the parent chain, choose the
chain with the greater number of substituents:
8. When branching first occurs at an equal distance from either end of the longest chain,
choose the name that gives the lower number at the first point of difference:
Strategy and Answer: The longest chain (shown in blue) contains seven carbon atoms;
therefore, the parent name is heptane. There are two methyl substituents (shown in red). We
number the carbon atoms so as to give the first methyl group a lower number. The correct name,
therefore, is 3,4-dimethylheptane. Numbering the chain from the other end to give 4,5-
dimethylheptane would have been incorrect.
SOLVED PROBLEM 2: Give the systematic name for the following alkane
Strategy and Answer: We are given with the condensed formula of the alkane. The longest
continuous chain extends from the upper left CH3 group to the lower left CH3 group and is seven
C atoms long:
Answer: Molecules (a), (b), and (c) represent 2-methylpentane while molecule (d) represent 3-
methylpentane.
Nomenclature of Cycloalkanes
Cycloalkanes are alkanes that form rings or cycles. The general formula is CnH2n.
1. Cycloalkanes with one ring and no substituents: Count the number of carbon atoms in
the ring, then add “cyclo” to the beginning of the name of the alkane with that number of
carbons. For example, cyclopropane has three carbons and cyclopentane has five carbons.
2. Cycloalkanes with one ring and one substituent: Add the name of the substituent to the
beginning of the parent name. For example, cyclohexane with an attached isopropyl group is
isopropylcyclohexane. For compounds with only one substituent, it is not necessary to specify
a number (locant) for the carbon bearing the substituent.
3. Cycloalkanes with one ring and two or more substituents: For a ring with two
substituents, begin by numbering the carbons in the ring, starting at the carbon with the
substituent that is first in the alphabet and number in the direction that gives the next
4. When a single ring system is attached to a single chain with a greater number of carbon
atoms, or when more than one ring system is attached to a single chain, then it is appropriate
to name the compounds as cycloalkylalkanes. For example,
SOLVED PROBLEM 4: Give the names for the following substituted alkanes:
1. Alkanes bearing halogen substituents are named in the IUPAC substitutive system as
haloalkanes:
2. When the parent chain has both a halo and an alkyl substituent attached to it, number the
chain from the end nearer the first substituent, regardless of whether it is halo or alkyl. If two
substituents are at equal distance from the end of the chain, then number the chain from the
end nearer the substituent that has alphabetical precedence:
3. Common names for many simple haloalkanes are still widely used, however. In this common
nomenclature system, called functional class nomenclature, haloalkanes are named as alkyl
halides. (The following names are also accepted by IUPAC.)
B. Alkenes contain at least one carbon-carbon double bond (C═C), and this is indicated in
the family name and in names for specific compounds by an -ene ending.
The IUPAC rules for naming alkenes are similar in many respects to those for naming
alkanes:
1. Determine the parent name by selecting the longest chain that contains the double bond and
change the ending of the name of the alkane of identical length from -ane to -ene. Thus, if the
longest chain contains five carbon atoms, the parent name for the alkene is pentene; if it
contains six carbon atoms, the parent name is hexene, and so on.
2. Number the chain so as to include both carbon atoms of the double bond and begin
numbering at the end of the chain nearer the double bond. Designate the location the double
bond by using the number of the first atom of the double bond as a prefix. The locant for the
alkene suffix may precede the parent name or be placed immediately before the suffix. We will
show examples of both styles:
3. Indicate the locations of the substituent groups by the numbers of the carbon atoms to which
they are attached:
Many older names for alkenes are still in common use. Ethene is often called ethylene, propene
is often called propylene, and 2-methylpropene is often called isobutylene.
4. Number substituted cycloalkenes in the way that gives the carbon atoms of the double bond
the 1 and 2 positions and that also gives the substituent groups the lower numbers at the first
point of difference. With substituted cycloalkenes it is not necessary to specify the position of
the double bond since it will always begin with C1 and C2. The two examples shown here
illustrate the application of these rules:
5. Name compounds containing a double bond and an alcohol group as alkenols (or
cycloalkenols) and give the alcohol carbon the lower number:
6. Two frequently encountered alkenyl groups are the vinyl group and the allyl group:
Using substitutive nomenclature, the vinyl and allyl groups are called ethenyl and prop-2-en-1-
yl, respectively. The following examples illustrate how these names are employed:
7. If two identical or substantial groups are on the same side of the double bond, the compound
can be designated cis; if they are on opposite sides it can be designated trans:
SOLVED PROBLEM 1: Give the IUPAC name for the following alkene:
Strategy and Answer: The longest chain contains 7 carbon atoms; thus, the parent name is
heptene. The double bond is located at C3 (between C3 and C4, numbered from left to right),
hence the IUPAC name is 3-heptene.
SOLVED PROBLEM 2: Give the IUPAC name for the following alkene:
Strategy and Answer: The longest chain contains 6 carbon atoms; thus, the parent name is
hexene. Substituents present are methyl, located at C2, and ethyl, located at C4. The double
bond is located at C1 (between C1 and C2, numbered from left to right), hence the IUPAC name
is 4-ethyl-2-methyl-1-hexene or 4-ethyl-2-methylhex-1-ene.
Strategy and Answer: We number the ring as shown below starting with the hydroxyl group so
as to give the double bond the lower possible number. We include in the name the substituent
(an ethenyl group) and the double bond (-ene-), and the hydroxyl group (-ol) with numbers for
their respective positions. Hence the IUPAC name is 3-ethenyl-2-cyclopenten-1-ol.
C. Alkynes contain at least one carbon-carbon triple bond (C≡C), and this is indicated in the
family name and in names for specific compounds by an -yne ending.
Nomenclature of Alkynes
2. When double and triple bonds are present, the direction of numbering is chosen so as to give
the lowest overall set of locants. In the face of equivalent options, then preference is given
to assigning lowest numbers to the double bonds.
3. The locations of substituent groups of branched alkynes and substituted alkynes are also
indicated with numbers. An −OH group has priority over the triple bond when numbering the
chain of an alkynol:
SOLVED PROBLEM 1: Give the IUPAC name for the following alkyne:
Strategy and Answer: The longest chain contains 7 carbon atoms and numbered as shown
below. Methyl substituent is located at C5 and the triple bond is located at C1 (between C1 and
C2). Hence, the name of the alkyne is 5-methyl-1-hexyne or 5-methylhex-1-yne.
SOLVED PROBLEM 2: Give the IUPAC name for the following alkyne:
Strategy and Answer: The longest chain contains 5 carbon atoms and numbered as shown
below. Two methyl substituents are both located at C4 and the triple bond is located at C1
(between C1 and C2). Hence, the name of the alkyne is 4,4-dimethyl-1-pentyne or 4,4-
dimethylpent-1-yne.
SOLVED PROBLEM 3: Give the IUPAC name for the following alkyne:
Strategy and Answer: The longest chain contains 5 carbon atoms and numbered as shown
below so as to give -OH group the lower number. Methyl and -OH substituents are both located
at C2 and the triple bond is located at C1 (between C1 and C2). Hence, the name of the alkyne
is 2-methyl-4-pentyn-2-ol or 2-methylpent-4-yn-2-ol.
D. Aromatic hydrocarbons contain a special type of ring, the most common example of which
is a benzene ring. There is no special ending in names for the general family of aromatic
compounds.
When a benzene ring is attached to some other group of atoms in a molecule, it is called a
phenyl group, and it is represented in several ways:
The combination of a phenyl group and a methylene group (−CH2−) is called a benzyl group:
Aryl halide is a compound with a halogen atom bonded to an aromatic ring such as a benzene
ring. If the aromatic ring is benzene, the aryl halide is called phenyl halide.
Functional groups are common and specific arrangements of atoms or bonds that impart
predictable reactivity and properties to a molecule.
The C═C double bonds in alkenes and C≡C triple bonds in alkynes are just two of the many
functional groups in organic molecules. The C―C single bonds and C―H in alkanes are not
considered functional groups because these bonds are present in molecules of almost all
organic compounds and are, in general, much less reactive than common functional groups.
Each kind of functional group often undergoes the same kinds of reactions in every molecule,
regardless of the size and complexity of the molecule. Thus, the chemistry of an organic
molecule is largely determined by the functional groups it contains.
Alcohols and phenols have the functional group ―OH called either the hydroxyl group or the
alcohol group which is attached to a sp3-hybridized carbon atom.
Alcohols have the general formula ROH.
The simplest alcohol is methanol, CH3OH. Another example of an alcohol is CH3CH2OH called
ethanol or ethyl alcohol.
Specific Example
Functional Compound
Suffix Systematic Name
Group Type or Class Structural Formula Ball-and-stick Model
(Common Name)
Two ways in viewing an alcohol structurally: (1) as hydroxyl derivative of alkanes and (2) as
alkyl derivatives of water. Ethyl alcohol, for example can be seen (1) as an ethane molecule
in which one hydrogen has been replaced by a hydroxyl group or (2) as a water molecule in
which one hydrogen has been replaced by an ethyl group.
As with alkyl halides, alcohols are classified into three groups: primary (1°), secondary (2°),
or tertiary (3°) alcohols. This classification is based on the degree of substitution of the
carbon to which the hydroxyl group is directly attached.
A. 1° alcohol – If the carbon atom bearing the hydroxyl group has only one other carbon
attached to it, the carbon is said to be a primary carbon and the alcohol is a primary
alcohol.
B. 2° alcohol – If the carbon atom bearing the hydroxyl group also has other two
carbon atoms attached to it, the carbon is said to be a secondary carbon and the
alcohol is a secondary alcohol.
C. 3° alcohol – If the carbon atom bearing the hydroxyl group has three other
carbons attached to it, this carbon is called a tertiary carbon and the alcohol is a
tertiary alcohol.
When a hydroxyl group is bonded to a benzene ring, the combination of the ring and the
hydroxyl group is called a phenol. Phenols differ significantly from alcohols in terms of their
relative acidity (phenols being relatively acidic than alcohols) and thus they are considered a
distinct functional group.
Nomenclature of Alcohols
The following procedure should be followed in giving alcohols IUPAC substitutive names:
1. Select the longest continuous carbon chain to which the hydroxyl is directly attached. Change
the name of the alkane corresponding to this chain by dropping the final -e and adding the
suffix -ol.
2. Number the longest continuous carbon chain so as to give the carbon atom bearing the
hydroxyl group the lower number. Indicate the position of the hydroxyl group by using this
number as a locant; indicate the positions of other substituents (as prefixes) by using the
numbers corresponding to their positions along the carbon chain as locants. The following
examples show how these rules are applied:
SOLVED PROBLEM 1: Give the IUPAC name for the following alcohol:
Strategy and Answer: The longest chain contains 3 carbon atoms and numbered as shown
below. A chlorine substituent is located at C3 and the hydroxyl group is located at C1. Hence,
the name of the alcohol is 3-chloro-1-propanol or 3-chloropropan-1-ol.
SOLVED PROBLEM 2: Give the IUPAC name for the following alcohol:
Strategy and Answer: The longest chain contains 5 carbon atoms and numbered as shown
below. Two methyl substituents are both located at C4 and the hydroxyl group is located at C2.
Hence, the name of the alcohol is 4,4-dimethyl-2-pentanol or 4,4-dimethylpropan-2-ol.
SOLVED PROBLEM 3: Give the IUPAC name for the compound shown:
Strategy and Answer: We find that the longest carbon chain (in red at right) has five carbons
and it bears a hydroxyl group on the first carbon. So, we name this part of the molecule as a 1-
pentanol. There is a phenyl group on C1 and a methyl group on C3, so the full name is 3-
methyl-1-phenyl-1-pentanol or 3-methyl-1-phenylpentan-1-ol.
Simple alcohols are often called by common functional class names that are also approved
by IUPAC. We have seen several examples already (Section 2.6). In addition to methyl alcohol,
ethyl alcohol, and isopropyl alcohol, there are several others, including the following:
Alcohols containing two hydroxyl groups are commonly called glycols. In the IUPAC
substitutive system, they are named as diols:
2. ETHERS
Ethers have the general formula ROR’ where R’ is an alkyl or phenyl group that may be same
or different from R.
Specific Example
Functional Compound
Suffix Systematic Name
Group Type or Class Structural Formula Ball-and-stick Model
(Common Name)
Ethers can be thought of as derivatives of water in which both hydrogen atoms have been
replaced by alkyl groups. The bond angle at the oxygen atom of an ether is only slightly larger
than that of water.
Examples of ethers are CH3OCH3 called methoxymethane ( or dimethyl ether) and
CH3CH2OCH3 called methoxyethane ( or ethyl methyl ether).
Nomenclature of Ethers
Simple ethers are frequently given common functional class names. One simply lists (in
alphabetical order) both groups that are attached to the oxygen atom and adds the word
ether:
IUPAC substitutive names should be used for complicated ethers, however, and for
compounds with more than one ether linkages.
1. In this IUPAC style, ethers are named as alkoxyalkanes, alkoxyalkenes, and alkoxyarenes.
The −OR group is an alkoxy group.
SOLVED PROBLEM 1: Give the IUPAC name for the following ether:
Strategy and Answer: The alkoxy group is methoxy group that is attached to C2 of the pentane
parent chain. Hence, the name of the ether is 2-methoxypentane.
SOLVED PROBLEM 2: Give the IUPAC name for the following ether:
Strategy and Answer: Two methoxy groups are attached to each carbon of the ethane parent
chain. Hence, the name of the ether is 1,2-dimethoxyethane.
SOLVED PROBLEM 3: Give the IUPAC name for the following ether:
Strategy and Answer: Ethoxy group is located at C1 and a methyl group is located at C4 of a
benzene ring. Hence, the name of the ether is 1-ethoxy-4-methylbenzene.
3. AMINES
Specific Example
Functional Compound
Suffix Systematic Name
Group Type or Class Structural Formula Ball-and-stick Model
(Common Name)
The other two hydrogens in the amino (―NH2) group can be replaced by organic groups.
Amines are classified as primary (1°), secondary (2°), or tertiary (3°) amines. This
classification is based on the number of organic groups that are attached to the
nitrogen atom.
Nomenclature of Amines
1. In systematic nomenclature they are named by adding the suffix -amine to the name of the
chain or ring system to which the NH2 group is attached with replacement of the final -e.
Methanamine Ethanamine
2. Most secondary and tertiary amines are named in the same general way. In systematic
nomenclature we use the locant N to designate substituents attached to a nitrogen atom.
N-methylethanamine N,N-diethylethanamine
SOLVED PROBLEM 1: Give the IUPAC name for the following amine:
Strategy and Answer: The longest chain contains 3 carbon atoms. The methyl substituent is
located at C2 and the amino group is attached to C1. Hence, the name of the amine is 2-methyl-
1-propanamine.
SOLVED PROBLEM 2: Give the IUPAC name for the following amine:
Strategy and Answer: The parent chain contains 2 carbon atoms. One H in the -NH2 group is
replaced by an ethyl substituent. Hence, the name of the amine is N-ethylethanamine.
SOLVED PROBLEM 3: Give the IUPAC name for the following amine:
Strategy and Answer: The longest chain contains 3 carbon atoms. Two Hs in the -NH2 group
are each replaced by methyl and ethyl substituents. Hence, the name of the amine is N-ethyl-
N-methyl-1-propanamine.
Aldehydes and ketones both contain the same functional group called the carbonyl group –
a group in which the carbon atom has a double bond to an oxygen atom.
4. ALDEHYDES
The carbonyl group of an aldehyde is bonded to one carbon atom and one hydrogen atom
(except for formaldehyde, which is the only aldehyde bearing two hydrogen atoms).
Aldehydes have the general formula RCHO. For formaldehyde, R is replaced with H.
Examples of aldehydes are HCHO called methanal or formaldehyde and CH3CHO called
ethanal or acetaldehyde.
Specific Example
Functional Compound
Suffix Systematic Name
Group Type or Class Structural Formula Ball-and-stick Model
(Common Name)
Nomenclature of Aldehydes
Aliphatic aldehydes are named in the IUPAC substitutive system by replacing the final -e of
the name of the corresponding alkane with -al.
1. Since the aldehyde group must be at an end of the carbon chain, there is no need to indicate
its position. When other substituents are present, the carbonyl group carbon is assigned
position 1.
2. Aldehydes in which the −CHO group is attached to a ring system are named by adding the
suffix carbaldehyde.
SOLVED PROBLEM 1: Give the IUPAC name for the following aldehyde:
Strategy and Answer: The parent chain contains 5 carbon atoms thus the parent name is
pentanal. A chloro substituent is attached to C5. Hence, the name of the aldehyde is 5-
chloropentanal.
SOLVED PROBLEM 2: Give the IUPAC name for the following aldehyde:
Strategy and Answer: The parent chain contains 2 carbon atoms thus the parent name is
ethanal. There is a phenyl substituent attached to C2 but we do not need to indicate 2- as a
locant because there is no other way that the phenyl group can the attached to an ethanal. Also,
we do not name the compound as carbaldehyde because the ring substituent is not directly
attached to the carbonyl carbon atom. Hence, the name of the aldehyde is phenylethanal.
SOLVED PROBLEM 3: Give the IUPAC name for the following aldehyde:
Strategy and Answer: The cyclohexane ring is directly attached to the carbonyl carbon atom,
hence the name of the aldehyde is cyclohexanecarbaldehyde.
5. KETONES
Nomenclature of Ketones
Aliphatic ketones are named by replacing the final -e of the name of the corresponding alkane
with -one.
1. The chain is numbered in the way that gives the carbonyl carbon atom the lower possible
number, and this number is used to designate its position.
SOLVED PROBLEM 1: Give the IUPAC name for the following ketone:
Strategy and Answer: The parent chain contains 5 carbon atoms numbered so as to give the
ketone functional group the lowest possible number, that is at C2. A double bond is located at
C4 (between C4 and C5). Hence, the name of the ketone is 4-penten-2-one or pent-4-en-2-one,
and not 1-penten-4-one.
SOLVED PROBLEM 2: Give the IUPAC name for the following ketone:
Strategy and Answer: The parent chain contains 2 carbon atoms and a phenyl substituent is
attached to C1, the carbonyl carbon atom. Hence, the name of the ketone is 1-phenylethanone.
Carboxylic acids, esters, and amides all contain a carbonyl group that is bonded to an oxygen
or nitrogen atom.
6. CARBOXYLIC ACIDS
The functional group present in carboxylic acids is ―COOH called carboxyl group (carbonyl
+ hydroxyl) – a carbonyl group bonded to a hydroxyl group.
Examples of carboxylic acids are methanoic acid (or formic acid), ethanoic acid (or acetic acid),
and benzoic acid.
Formic acid is an irritating liquid produced by ants. (The sting of the ant is caused, in part,
by formic acid being injected under the skin. Formic is the Latin word for ant.) Acetic acid,
the substance responsible for the sour taste of vinegar, is produced when certain bacteria act
on the ethyl alcohol of wine and cause the ethyl alcohol to be oxidized by air.
Systematic or substitutive names for carboxylic acids are obtained by dropping the final -e of
the name of the alkane corresponding to the longest chain in the acid and by adding -oic acid.
The carboxyl carbon atom is assigned number 1.
Benzoic acid
SOLVED PROBLEM 1: Give the IUPAC name for the following carboxylic acid:
Strategy and Answer: The longest chain contains 6 carbon atoms thus the parent name is
hexanoic acid. A methyl substituent is located at C4 hence, the name is 4-methylhexanoic acid.
SOLVED PROBLEM 2: Give the IUPAC name for the following carboxylic acid:
SOLVED PROBLEM 3: Give the IUPAC name for the following compound.
Strategy and Answer: This chain contains six carbons with one double bond, so the base name
is hexenoic acid. Then we give the position of the double bond at C2, and a chloro substituent
at C5. The name, therefore, is 5-chloro-2-hexenoic acid.
7. ESTERS
Esters have the general formula RCOOR’ where the carbonyl group is bonded to an alkoxyl
group (―OR).
Example of an ester is ethyl ethanoate and pentyl butanoate (smells like apricots and pears).
Our body makes esters from long-chain carboxylic acids called “fatty acids” by combining
them with glycerol.
Nomenclature of Esters
The names of esters are derived from the names of the alcohol (with the ending -yl) and the
acid (with the ending -ate or -oate). The portion of the name derived from the alcohol comes
first:
SOLVED PROBLEM 1: Give the IUPAC name for the following ester:
Strategy and Answer: The alcohol derivative is 3-methylbutyl or isopentyl, and the carboxylic
acid derivative contains 2 carbon atoms. Hence, the name of the ester is 3-methylbutyl
ethanoate or isopentyl ethanoate. Isopentyl ethanoate is used in synthetic banana flavor.
SOLVED PROBLEM 2: Give the IUPAC name for the following ester:
Strategy and Answer: The alcohol derivative is 3-methylbutyl or isopentyl, and the portion that
is a carboxylic acid derivative contains 5 carbon atoms in straight-chain. Hence, the name of
the ester is 3-methylbutyl pentanoate or isopentyl pentanoate. Isopentyl pentanoate is used in
synthetic apple flavor.
SOLVED PROBLEM 3: Give the IUPAC name for the following ester:
8. AMIDES
Amides have the general formula RCONH2, RCONHR’, or RCONR’R” where a carbonyl group
is bonded to a nitrogen atom bearing (1) two hydrogens; (2) hydrogen and alkyl group; or (3)
two alkyl groups.
Nomenclature of Amides
1. Amides that have no substituent on nitrogen are named by dropping -ic acid from the
common name of the acid (or -oic acid from the substitutive name) and then adding -amide.
Ethanamide
2. Alkyl groups on the nitrogen atom of amides are named as substituents, and the named
substituent is prefaced by N- or N,N-.
N-methylethanamide N,N-dimethylethanamide
SOLVED PROBLEM 1: Give the IUPAC name for the following amide:
Strategy and Answer: The longest chain contains 5 carbon atoms, and a methyl substituent is
located at C2. Hs in -NH2 group are not replaced by any substituent. Hence, the name of the
amide is 2-methylpentanamide.
SOLVED PROBLEM 2: Give the IUPAC name for the following amide:
Strategy and Answer: The parent chain contains 2 carbon atoms. Phenyl and propyl
substituents replace the Hs in -NH2 group. Hence, the name of the amide is N-phenyl-N-
propylethanamide.
Exercises / Activities
A. 4-Ethyl-2,6-diisopropylnonane
B. 6-Ethyl-4,8-diisopropylnonane
C. 6-Ethyl-4-isopropyl-8,9-dimethyldecane
D. 5-Ethyl-7-isopropyl-2,3-dimethyldecane
4. What is the IUPAC name for the compound whose bond-line structural formula is given
below?
A. 5-Bromo-3-chloro-6-ethylheptane
B. 3-Bromo-5-chloro-2-ethylheptane
C. 4-Bromo-6-chloro-3-methyloctane
D. 1-Bromo-3-chloro-1-(1-Methylpropyl)pentane
5. What is the IUPAC name for the compound whose bond-line structural formula is given
below?
A. 1-Chloro-2,4-dimethylcyclohexane
B. 4-Chloro-1,5-dimethylcyclohexane
C. 6-Chloro-1,3-dimethylcyclohexane
D. 1-Chloro-4,6-dimethylcyclohexane
A. 5-Isopropyl-2-hexene
B. 5,6-Dimethyl-2-heptene
C. 2,3-Dimethyl-5-heptene
D. 5,6,6-Trimethyl-2-hexene
A. 2-Octyne
B. 6-Octyne
C. 5,5-Dimethyl-2-hexyne
D. 2,2-Dimethyl-4-hexyne
A. 2,4-Dimethyl-5-pentanol
B. 2,4-Dimethyl-1-pentanol
C. 3-Isopropyl-2-methyl-1-propanol
D. 1-Isopropyl-2-methyl-3-propanol
A. Propoxyethane
A. N,N-Diethyl-2-ethyl-1-propanamine
B. N,N-Diethyl-2-methyl-1-butanamine
C. N,N-Dimethyl-2-ethyl-1-butanamine
D. N,N-Dimethyl-2-ethyl-1-propanamine
A. Butanal
B. Propanal
C. 3-Methylbutanal
D. 2-Methylpropanal
A. 6-Methyl-3-heptanone
B. 2-Methyl-5-heptanone
C. 5-isopropyl-3-hexanone
D. 6,6-Dimethyl-3-hexanone
13. What is the IUPAC name for the following carboxylic acid?
A. 1-Phenylhexanoic acid
B. 5-Phenylhexanoic acid
C. 1-Phenylpentanoic acid
D. 5-Phenylpentanoic acid
A. Ethyl benzoate
B. Propyl benzoate
C. Phenyl ethanoate
D. Phenyl propanoate
A. N-Cyclopropyl-5-methylhexanamide
B. N-Cyclopropyl-4-methylpentanamide
C. N-Cyclopropyl-4-isopropylbutanamide
D. N-Cyclopropyl-3-isopropylpropanamide
Activity 2 – What Am I?
What to do: Identify each of the following compounds as an alkane, alkene, alkyne, alcohol,
aldehyde, amine, and so forth.
***Note that the class of compound can be used to name the functional group present in a
compound. For example: for the class aldehydes and ketones, the functional group is carbonyl,
but when asked to identify functional groups present in a compound and it happens to have a
carbonyl, it is accepted to say aldehyde or ketone, instead of carbonyl, for specificity.
Capsaicin
Reflection: Choose one organic compound that can be found in your household and provide the
following information:
a. Chemical Name and Chemical Formula of the organic compound
b. Structure of the organic compound and identify the functional group/s present
c. Use of the organic compound in everyday life
d. Effects of the organic compound to humans and other living things
2 (NEEDS 4 (EXCEEDS
3 (MEETS
CRITERIA 1 (NOT VISIBLE) IMPROVEMENT) EXPECTATIONS)
EXPECTATIONS)
Few of the required
elements are clearly Most of the required All of the required
Missing most or all
REQUIRED visible, organized and elements are clearly elements are clearly
of the required
ELEMENTS visible, organized visible, organized
elements. well placed. May be
and well placed. and well placed.
missing elements.
The project needs The project has an
The project has a
significant The project needs excellent design and
VISUAL CLARITY nice design and
improvement in improvement in design, layout. It is neat and
AND APPEAL layout. It is neat and
design, layout and layout or neatness. easy to understand
easy to read.
neatness. the content.
The student’s Few of the drawings Most drawings and Drawings and
DRAWINGS/ and graphics are clear
drawings are not graphics are clear graphics are clear
GRAPHICS and relevant.
clear or relevant. and relevant. and relevant.
Almost no
Many grammatical, A few grammatical, No grammatical,
grammatical, spelling
MECHANICS spelling or spelling or punctuation spelling or
or punctuation
punctuation errors. errors. punctuation errors.
errors.
e. Safety precautions in using the organic compound
Rubric:
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.
Answer Key
Activity 1
1. C 6. B 11. D
2. B 7. C 12. A
3. D 8. B 13. D
4. C 9. B 14. D
5. A 10. B 15. B
Activity 2
a. Ketone d. Aldehyde
b. Alkyne e. Alcohol (2°)
c. Alcohol (2°) f. Alkene
Activity 3
ORGANIC COMPOUNDS
Learning Competency:
Specific Objective:
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 of 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:
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)
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 C3H7Cl 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 C4H10O.
Alcohols:
Ethoxyethane (C4H10O)
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 CnH2n-2 Thus, 1-pentyne and 2-pentyne are constitutional isomers of cyclopentene.
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
Key Concepts
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 insufficient supply of oxygen in the process. Incomplete combustion
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:
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, contain large amount of octane. Combustion of octane proceeds as
follows:
𝟐 𝑪𝟖 𝑯𝟏𝟖 (𝒍) + 𝟐𝟓𝑶𝟐 (𝒈) → 𝟏𝟔𝑪𝑶𝟐 (𝒈) + 𝟏𝟖𝑯𝟐 𝑶(𝒍)
EXAMPLE 5: Ethanol, C2H5OH, can be used as a fuel source in an alcohol lamp. Combustion
of ethanol can be written as:
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.
(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.
To promote the reaction, the reaction temperature must be raised 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 in order for the reaction to occur. The most
widely used catalysts are finely divided metals on which H2 is adsorbed.
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 is one that can potentially yield two or more constitutional isomers
but that actually produces only one (or a predominance of one).
SOLVED PROBLEM 1: What is the main product in the addition of HBr to propene?
+ 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?
+ 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
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.
Strategy and Answer: The product of hydrogenation of ethene is the alkane ethane, C2H6.
+ H―H
+ H―H
Strategy and Answer: When cyclohexene undergoes hydrogenation reaction, the product is
cyclohexane.
+ H―H
Addition reaction of alkynes proceeds with the same conditions and catalysts as the addition
reaction of alkenes.
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 the same halogen attached to a same carbon atom.
Both additions are regioselective and follow Markovnikov’s rule:
SOLVED PROBLEM 1: What is the product when 1-hexyne undergoes addition reaction with
(a) one molar equivalent of hydrogen bromide; (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) Addition of two molar equivalents of hydrogen bromide to 1-hexyne further reduces
2-bromo-1-hexene to 2,2-dibromohexane.
(a)
+ H―Br
+ 2 H―Br
B. Hydrogenation of Alkynes
SOLVED PROBLEM 1: What is the product of hydrogenation of ethyne, C2H2, with (a) one molar
equivalent of hydrogen; (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
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 reaction of a carboxylic acid, acid chloride, or
carboxylic acid anhydride with an alcohol or phenol.
Acid-Catalyzed Esterification
HA is an acid used as catalyst with the application of heat and the double arrow indicates
that the reaction is reversible.
Strategy and Answer: When benzoic acid reacts with methanol, the product is methyl benzoate
and water.
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.
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.
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?
+ 3 NaOH +
1. 5.
2. 6.
3. 7.
4. 8.
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 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 hydrogenation of 2,3-dimethyl-1-heptyne with (a) one molar equivalent
of hydrogen, (b) two molar equivalents of hydrogen? Write the chemical equation using
structural formulas of the reactants and the product.
Reflection
1. Why do we need to study organic chemistry? Why do we need to study reactions of organic
compounds?
2. Almost everyday in human activity involves combustion of fuels which is one of the many causes
of anthropogenic (man-made) emissions of pollutants in our environment. As a student of
chemistry, what will you do to mitigate the effects of global warming and climate change due to
increasing carbon footprint in the atmosphere?
Rubric:
Meets Approaching Below
Above Expectations Expectations Expectations
Expectations (4) (3) (2) (1)
The reflection attempts
The reflection explains the The reflection
to demonstrate The reflection does
student’s own thinking explains the
thinking about learning not address the
and learning processes, asstudent’s thinking
Reflective but is vague and/or student’s thinking
well as implications for about his/her own
Thinking unclear about the and/or learning.
future learning. learning processes.
personal learning
process.
The reflection
The reflection attempts
articulates
to articulate
connections
The reflection articulates connections between
between this
multiple connections this learning The reflection does
learning
between this learning experience and content not articulate any
experience and
Making experience and content from other courses, connection to other
content from
Connections from other courses, past past learning learning or
other courses,
learning, life experiences experiences, or experiences.
past learning
and/or future goals. personal goals, but the
experiences,
connection is vague
and/or future
and/or unclear.
goals.
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.
Answer Key
Activity 1
1. C 6. B 11. B
2. A 7. C 12. A
3. A 8. A 13. A
4. A 9. C 14. C
5. A 10. A 15. A
Activity 2