SELF LEARNING

MODULE
GENERAL CHEMISTRY 1
Antipolo City National Science and Technology High School

Jasmine Kate L. Esparagoza, RCh

Special Science Teacher 1

TABLE OF CONTENTS
 LESSON Learning Competency Pages
1. Determine the polarity of simple molecules
2. Describe the different functional groups
3. Describe structural isomerism; give examples
4. Describe some simple reactions of organic compounds: combustion of organic
fuels, addition, condensation, and saponification of fats

How to Learn from this Module

To achieve the objectives, you are to do the following:

• Take your time reading the lessons carefully.

• Follow the directions and/or instructions in the activities and exercises diligently.

• Answer all the given tests and exercises

What I Need To Know This part contains learning objectives that are set for you
to learn as you go along the module.

What I know This is an assessment as to your level of knowledge to

the subject matter at hand, meant specifically to gauge
prior related knowledge
What’s In This part connects previous lesson with that of the
current one.

What’s New An introduction of the new lesson through various

activities, before it will be presented to you

What is It These are discussions of the activities as a way to

deepen your discovery and understanding of the
concept.
What’s More These are follow-up activities that are intended for you to
practice further in order to master the competencies

What I Have Learned Activities designed to process what you have learned
from the lesson

What I can do These are tasks that are designed to show- case your
skills and knowledge gained, and applied into real-life
concerns and situations

WHAT I NEED TO KNOW?

 Just as individual bonds are often polar, molecules are often polar also. Molecular polarity results from the
vector summation of all individual bond polarities and lone-pair contributions in the molecule. As a practical matter,
strongly polar substances are often soluble in polar solvents like water, whereas less polar substances are insoluble
in water. In this chapter you will determine the direction of the dipole moment in a compound.

Closely related to the ideas of bond polarity and dipole moment is the concept of assigning formal charges
to specific atoms within a molecule, particularly atoms that have an apparently “abnormal” number of bonds. Look
at dimethyl sulfoxide (CH3SOCH3), for instance, a solvent commonly used for preserving biological cell lines at low
temperature. The sulfur atom in dimethyl sulfoxide has three bonds rather than the usual two and has a formal
positive charge. The oxygen atom, by contrast, has one bond rather than the usual two and has a formal negative
charge. Note that an electrostatic potential map of dimethyl sulfoxide shows the oxygen as negative (red) and the
sulfur as relatively positive (blue), in accordance with the formal charges

WHAT’S IN?

You have learned from the previous lesson the electronegativity of elements in the periodic table and the
bonds between atom. Now, look back on the structures and the electronegativity given below. Bonds between
carbon and more electronegative elements such as oxygen (EN = 3.5) and nitrogen (EN 5=3.0), the bonding
electrons are drawn away from carbon toward the electronegative atom. This leaves carbon with a partial positive
charge, and the electronegative atom with a partial negative charge.

WHAT IS IT?

Dipole Moment

Net molecular polarity is measured by a quantity called the dipole moment and can be thought of in the
following way: assume that there is a center of mass of all positive charges (nuclei) in a molecule and a center of
mass of all negative charges (electrons). If these two centers do not coincide, then the molecule has a net polarity.
The dipole moment, a vector, is directed along the line from negative charge toward positive charge. It is the
measure of net molecular polarity, The larger the difference in electronegativities of bonded atoms, the larger the
dipole moment. For example, NaCl has the highest dipole moment because it has an ionic bond (i.e. highest charge
separation).

The sum of all the bond dipoles on a molecule is referred to as the molecule’s dipole moment. Molecule
dipole moments are useful in predicting the solubility of organic molecules. For example, by using dipole moments,
you can predict that oil and water will not mix and will be insoluble in each other, whereas water and alcohol will
mix. Solubilities are important for practical organic chemistry because it is hard to get a reaction between two
molecules that do not dissolve in the same solvent.

You represent this separation of charge on paper with a funny-looking arrow called the dipole vector. The
head of the dipole vector points in the direction of the partially negatively charged atom (the more electronegative
atom) and the tail (which looks like a + sign) points toward the partially positive atom of the bond (the less
electronegative atom).
Even small molecules like water, methanol, and ammonia, have substantial dipole moments, however, both
because they contain strongly electronegative atoms (oxygen and nitrogen) and because all three molecules have
lone-pair electrons. The lone-pair electrons on oxygen and nitrogen atom stick out into space away from the
positively charged nuclei, giving rise to a considerable charge separation and making a large contribution to the
dipole moment.

In contrast, carbon dioxide, methane, ethane, and benzene have zero dipole moments. Because of the symmetrical
structures of these molecules, the individual bond polarities and lone-pair contributions exactly cancel.

ẟ- ẟ+ ẟ- Oxygen is more electronegative than Carbon, so in this bond, the bonding electrons spend
more time around chlorine than around carbon. Therefore, the Oxygen holds a partial negative
charge and the carbon holds a partial positive charge. The bond dipole for this molecule is polar
but CO2 is linear so the two dipoles are pointing in exactly opposite directions and cancel. This
makes the molecule as a whole non-polar.

Carbon is more electronegative than Hydrogen. C-H bonds are polar, but CH4 is Tetrahedral, the
dipoles cancel. Making CH4 a non-polar molecule.

Like the previous sample, C-H bonds are polar, but Ethane molecule is non-polar

Benzene is a hydrocarbon that contains only C-C and C-H bonds.

Carbon is slightly more electronegative than H, so a C-H bond is very slightly polar and moment.
The bond dipoles cancel exactly, so benzene has a zero-dipole moment. Benzene is nonpolar
because it is a symmetrical molecule in which all the bond dipoles cancel.

Formal Charges
Formal charges, as the name suggests, are a formalism and do not imply the presence of actual ionic charges in a
molecule. The goal of formal charge is to"de-emphasize" bond polarity by assuming that all electrons are shared
equally. Formal charges are helpful for coordinate covalent bonding. In methane, for instance, the carbon atom
owns one electron in each of the four C-H bonds, for a total of four. Because a neutral, isolated carbon atom has
four valence electrons, and because the carbon atom in methane still owns four, the methane carbon atom is
neutral and has no formal charge.

The same is true for the nitrogen atom in ammonia, which has three covalent N-H bonds and two nonbonding
electrons (a lone pair). Atomic nitrogen has five valence electrons, and the ammonia nitrogen also has five—one in
each of three shared N-H bonds plus two in the lone pair. Thus, the nitrogen atom in ammonia has no formal charge.
The situation is different in dimethyl sulfoxide. Atomic sulfur has six valence electrons, but the dimethyl sulfoxide
sulfur owns only five—one in each of the two S-C single bonds, one in the S-O single bond, and two in a lone pair.
Thus, the sulfur atom has formally lost an electron and therefore has a positive charge. A similar calculation for the
oxygen atom shows that it has formally gained an electron and has a negative charge. Atomic oxygen has six valence
electrons, but the oxygen in dimethyl sulfoxide has seven—one in the O-S bond and two in each of three lone pairs.

To express the calculations in a general way, the formal charge on an atom is equal to the number of valence
electrons in a neutral, isolated atom minus the number of electrons owned by that bonded atom in a molecule. The
number of electrons in the bonded atom, in turn, is equal to half the number of bonding electrons plus the
nonbonding, lone-pair electrons.

A summary of commonly encountered formal charges and the bonding situations in which they occur is given in
Table.

FUNCTIONAL GROUPS

The structural features that make it possible to classify compounds into families are called functional
groups. A functional group is a group of atoms within a molecule that has a characteristic chemical behavior.
Chemically, a given functional group behaves in nearly the same way in every molecule it is a part of. For example,
compare ethylene, a plant hormone that causes fruit to ripen, with menthene, a much more complicated molecule
found in peppermint oil. Both substances contain a carbon–carbon double-bond functional group, and both
therefore react with Br2 in the same way to give a product in which a Br atom has added to each of the double-
bond carbons. This example is typical: the chemistry of every organic molecule, regardless of size and complexity,
is determined by the functional groups it contains.
Given in the table below are the functional groups

Name Structure Name Ending Example

-ene
Alkene Ethene

-yne
Alkyne Ethyne

None

Arene (Aromatic Ring) Benzene

None
Chloromethane
Halide X = Halogens

-ol
Alcohol Alcohol

ether

Ether Dimethyl ether

-amine

Amine Methylamine

-nitrile
Nitrile Ethanenitrile

-thiol
Thiol Methanethiol

sulfide
Dimethylsulfide
Sulfide

-al
Ethanal

Aldehyde
 -one

Propanone
Ketone

-oic acid

Carboxylic Acid
Ethanoic acid

-oate

Methyl ethanoate
Ester

For this lesson, the focus will be on naming functional groups but substituent name will be
introduced andnomenclature for alkene, alkyne and aromatic ring will be on separate lesson.

Nomenclature of Functional Groups

Rules in Naming Some Organic

Parent and Substituent Names Compounds

Number of Carbons Substituent Name (-yl) Parent Name (-ane)

Rule 1: Select the longestcarbon
chain containing the functional
1 Methyl Methane group, and derive the parent
name by replacing the -e ending
2 Ethyl Ethane of the corresponding alkane with
correct ending based on the
functional group.
3 Propyl Propane
The -e is deleted to prevent
4 Butyl Butane the occurrence of twoadjacent
vowels.
5 Pentyl Pentane
Rule 2: Number the alkanechain
6 Hexyl Hexane beginning at the end nearer the
functional group.
7 Heptyl Heptane
Rule 3: Number the substituents
according to their position on the
8 Octyl Octane
chain,and write the name, listing
the substituents in alphabetical
9 Nonyl Nonane order and identifying the
position to which the functional
10 Decyl Decane groupis bonded.
 Halide

Although commonly called alkyl halides, halogen-substituted alkanes are named systematically as
haloalkanes,treating the halogen as a substituent on a parent alkane chain.

In naming Alkyl Halides the rules above are followed except that the number the carbons of the parent chain
beginning at the end nearer the first substituent, whether alkyl or halo.

If the parent chain can be properly numbered from either end by step 2, begin at the end nearer the
substituentthat has alphabetical precedence

ALCOHOL

Alcohols are classified as primary (1°), secondary (2°), or tertiary (3°), depending on the number of organic
groups bonded to the hydroxyl-bearing carbon.

THIOL

Thiols, sometimes called mercaptans, are sulfur analogs of alcohols. They are named by the same system used for
alcohols, with the suffix -thiol used in place of -ol. The -SH group itself is referred to as a mercapto group.

ETHER

This functional group does not follow the stated rule above, ethers with no other functional groups are named by
identifying the two organic substituents and adding the word ether as in the formula R1–O–R2. (R = hydrocarbon
i.e. methyl, ethyl

Based from the table, methyl has one carbon, assign methyl as R1. Propyl has three carbon, assign propyl as R2.
Oxygen is bonded to the second carbon of propyl, the name becomes isopropyl. Arrange the name
alphabeticallyand add ether, that would lead you to Isopropyl methyl ether
 Additional Examples

SULFIDE

Sulfides are the sulfur analogs of ethers just as thiols arethe sulfur analogs ofalcohols. Sulfides are named by
following the same rules used for ethers, with sulfide used in place of ether for simple compounds.

ALDEHYDE

Aldehydes are named by replacing the terminal -e of the corresponding alkane name with -al. The parent
chainmust contain the -CHO group, and the -CHO carbon is numbered as carbon 1.

Common Names of Some Simple Aldehydes

Formula Common Name Systematic Name

HCHO Formaldehyde Methanal

CH3CHO Acetaldehyde Ethanal

H2C CHCHO Acrolein Propenal

KETONE

Ketones are named by replacing the terminal -e of the corresponding alkane name with -one. The parent chain
isthe longest one that contains the ketone group, and the numbering begins at the end nearer the carbonyl
carbon. As with alkenes and alcohols the locant is placed before the parent name in older rules but before the
suffix in newer IUPAC recommendations.
CARBOXYLIC ACID

Simple carboxylic acids derived from open-chain alkanes are systematically named by replacing the terminal -
eof the corresponding alkane name with -oic acid. The -CO2H carbon atom is numbered C1.

We’ll use systematic names in this book, with a few exceptions such as formic (methanoic) acid and acetic
(ethanoic) acid, whose names are accepted by IUPAC and are so well known that it makes little sense to refer
tothem any other way

Common Names of Some Carboxylic Acids and Acyl Groups

Structure Name Acyl Group

HCO2H Formic Formyl

CH3CO2H Acetic Acetyl

CH3CH2CO2H Propionic Propionyl

CH3CH2CH2CO2H Butyric Butyryl

HO2CCO2H Oxalic Oxalyl

HO2CCH2CO2H Malonic Malonyl

HO2CCH2CH2CO2H Succinic Succinyl

ESTERS

Esters are named by first identifying the alkyl group attached to oxygen and then the carboxylic acid, with the
-ic acid ending replaced by -ate.

NITRILE

Compounds containing the -C-N functional group are called nitriles and undergo some chemistry similar to
thatof carboxylic acids. Simple open-chain nitriles are named by adding -nitrile as a suffix to the alkane name,
with the nitrile carbon numbered C1.
 Nitriles can also be named as derivatives of carboxylic acids by replacing the -ic acid or -oic acid ending
with -onitrile, or by replacing the -carboxylic acid ending with -carbonitrile. The nitrile carbon atom is
attached to C1 but is not itself numbered.

If another carboxylic acid derivative is present in the same molecule, the prefix cyano- is used
for the Cgroup.

AMINE

Amines can be either alkyl-substituted (alkylamines) or aryl-substituted (arylamines). Although much

of the chemistry of the two classes is similar, there are also substantial differences. Amines are
classified as primary(RNH2), secondary (R2NH), or tertiary (R3N), depending on the number of organic
substituents attached to nitrogen. Thus, methylamine (CH3NH2) is a primary amine, dimethylamine
[(CH3)2NH] is a secondary amine,and trimethylamine [(CH3)3N] is a tertiary amine.

Amines with more than one functional group are named by considering the -NH2 as an amino substituent
on theparent molecule.

ISOMERS

Isomers always have the same chemical formula. When the chemical formulae are different, then the compounds
are completely different. Important information can be gained from the chemical formulas when comparing
compounds.

Structural (constitutional) isomers

They have the same molecular formula but a different bonding arrangement among the atoms. Stereoisomers
have identical molecular formulas and arrangements of atoms. They differ from each other only in the spatial
orientation of groups in the molecule. For organic chemistry, there are several types of stereoisomers:
enantiomers, diastereoisomers, geometric isomers, and conformers. These stereoisomers will be introduced and
explained throughout several chapters
The compounds below have the same molecular formula (C2H6O), yet they differ from each other in the way the
atoms are connected—that is, they differ in their constitution. As a result, they are called constitutional isomers.
Constitutional isomers have different physical properties and different names. The first compound is a colorless gas
used as an aerosol spray propellant, while the second compound is a clear liquid, commonly referred to as “alcohol,”

found in alcoholic beverages.

Chain Isomerism

A variety of structural isomer tha arise because of the possibility of branching in carbon chains. For example, there
are two isomers of butane, C4H10. In one of them, the carbon atoms lie in a "straight chain" whereas in the other

the chain is branched.

Position Isomerism

In position isomerism, the basic carbon skeleton remains unchanged, but important groups are moved around on
that skeleton.

For example, there are two structural isomers with the molecular formula C3H7Br. In one of them the bromine
atom is on the end of the chain, whereas in the other it's attached in the middle.

Another similar example occurs in alcohols such as C4H9OH

Functional group isomerism

In this variety of structural isomerism, the isomers contain different functional groups - that is, they belong to
different families of compounds.
A molecular formula C3H6OC3H6O could be either propanal (an aldehyde) or propanone (a ketone).

There are other possibilities as well for this same molecular formula - for example, you could have a carbon-carbon
double bond (an alkene) and an -OH group (an alcohol) in the same molecule.

Identifying Constitutional Isomers

1. Identify whether the following two compounds are constitutional isomers or whether they are simply
different drawings of the same compound:

Solution

Use the rules of nomenclature to name each compound. In each case, identify the parent, locate the substituents,
number the parent, and assemble a name:

These compounds have the same name, and therefore, they are not constitutional isomers. They are actually two
representations of the same compound.

WHAT’S MORE?

POLARITY

A. Calculate the formal charges on the indicated atoms in each compound below

1. The formal charge on phosphorous is .

2. The formal charge on oxygen A is .
3. The formal charge on carbon is .
4. The formal charge on oxygen is .
5. Determine if the molecule is polar or non-polar
 B. Draw Lewis structures, give the molecular geometry and indicate polar or non-polar for the following
molecules:
a. CS2
b. OF2
c. IF5
d. CH3Cl
e. SO2

FUNCTIONAL GROUPS

1. Propose structure for the following

a. A ketone, C4H8O
b. A nitrile, C5H9N

2. Identify the functional group/s present.

a. b.

3. Draw the following organic compounds, and state the organic family they belong to.
a. Heptanal
b. Propanoic acid
c. 3-hexanone
4. Name the following organic compounds. Circle the functional group if one is present

a. b.

ISOMERS

1. Draw structures for all constitutional isomers with the following molecular formulas:
a. C4H10
b. C5H12
2. For each pair of compounds, identify whether they are constitutional isomers or two representations of the
same compound:

3. There are two constitutional isomers with molecular formula C3H7Cl, because there are two possibilities for
the location of the chlorine atom. It can be connected either to the central carbon atom or to one of the
other two (equivalent) carbon atoms. Draw both isomers

WHAT I HAVE LEARNED

1. What are functional groups?

2. Explain the rules in naming compounds
3. What is dipole moment?
4. Are molecules with polar bond dipole are also dipole molecules?
5. What is the importance of calculating formal charge?
REFERENCES

Organic Chemistry 8th Edition – McMurry

https://www.britannica.com/science/electric-dipole

https://chem.libretexts.org/Bookshelves/Physical_and_Theoretical_Chemistry_Textbook_Maps/Supplemental_
Modules_(Physical_and_Theoretical_Chemistry)/Physical_Properties_of_Matter/Atomic_and_Molecular_Prope
rties/Intermolecular_Forces/Specific_Interactions/Dipole_moments