MODULE 3.

A. FUNCTIONAL GROUPS

Because compounds of carbon are so numerous, it is convenient to organize them into families
that exhibit similarities.

HYDROCARBONS
 simplest class of organic compounds.
 Compounds composed only of carbon and hydrogen.

The key structural feature of hydrocarbons, is the presence of the stable carbon-carbon bond.
Carbon is the only element capable of forming stable, extended chains of atoms bonded
through single, double or triple bond.

FOUR GENERAL TYPES OF HYDROCARBON

a. Alkanes
b. Alkenes
c. Alkynes
d. Aromatic Hydrocarbons

The members of these different classes of hydrocarbons exhibit different chemical nehaviors
but also have similarities.
a. Because carbon and hydrogen do not differ greatly in electronegativity (2.5 for
carbon, 2.1 for hydrogen), hydrocarbon molecules are relatively nonpolar hence are
almost completely insoluble in water, but they dissolve readily in other nonpolar
solvent.
b. They tend to become less volatile with increasing molar mass because of London
dispersion forces.
Carbon combines with other atoms to form characteristics structural units called
FUNCTIONA GROUPS.

IMPORTANCE OF FUNCTIONAL GROUPS

a. They are the units by which we divide organic compounds into classes.
b. They are the sites of chemical reaction.
c. Serves as a basis for naming organic compounds.

1. ALCOHOLS: has the characteristics structural feature of a carbon bonded to the –OH
(hudroxyl) group.
Ex. CH3CH2OH – ethanol

2. ALDEHYDES AND KETONES: contains C=O (carbonyl) group.

Ex.

3. CARBOXYL ACIDS: Acids have the characteristic structural feature of –CO2H

(Carboxyl; carbonyl + hydroxyl) group. The carboxyl group may be written in any of the folloeing
ways, all of which are equivalent.

RCOOH RCO2H
SOME FUNCTIONAL GROUPS
 B. MOLECULAR AND STRUCTURAL FORMULA

MOLECULAR FORMULA: shows the number of each typeof atom that is present in the molecule
of the compound.
Ex. C2H6
STRUCTURAL FORMULA: shows the detail of the bonding present in the molecule, i.e. which
atom is connected to which other atom.

WRITING STRUCTURAL FORMULA

1. FULL OR EXPANDED STRUCTURAL FROMULA: all the atoms and bonds are indicated.
Example:

2. CONDENSED STRUCTURAL FORMULA: an abbreviated form of writing formulas.

 Shows no bonds
 Shows all carbon-carbon bonds but no carbon-hydrogen bonds.
Example: CH3CH2
3. SKELETON STRUCTURAL FORMULA: shows only the carbon atom in the molecules.

4. LINE STRUCTURAL FORMULA: uses lines to show the structure of the compound.
 Carbon atoms are present at the intersection of two or more lines wherever a line
begins or ends.
 Hydrogen atoms bonded to carbon are not shown. Because carbon always has a
valence of four, we mentally supply the correct number of hydrogens
 All atoms other than carbon and hydrogen are shown.

Example:

C. ISOMERISM

Isomers: are compounds that have the same molecular formula but different structures.
 Although isomers are composed of the same collection of atoms, they differ in one or
more physical or chemical properties such as color, solubility, or rate of reaction with
some reagents.
Structural Isomers: are compounds that have the same molecular formula but different structures.

Example: C4H10 CH3CH2CH2CH3 CH3CHCH3

 CH3
Butane Isobutane
Stereoisomers: have the same molecular formula, the same order of attachment of atoms in their
molecules but a different three-dimensional orientation of their atoms in space.
Example:

TWO GROUPS OF STEREOISOMER

1. Enantiomers: stereoisomers that are non-superimposable mirror images.

Example:

2. Diastereomers: Stereisomers that are not mirror images.

Mirror image: is the reflection of an object in a mirror.

Chiral: from the greek word “cheir” meaning hand, objects that are not superimposable on the
mirror image. They shoe handedness.
Example: Your left hand and right hand are chiral

NOTE: Enantiomers are different compounds hence have different physical properties one which is
their effect on the plane of polarized light.

C. THE IUPAC SYSTEM (International Union of Pure and Applied Chemistry)

General system of writing nomenclature.
The name assigned to any compound with a chain of carbon atom consists of three parts: a
prefix, an infix(a modifying element inserted into a word) and a suffix. Each part provides
information about the structural formula of the compounds.
o Prefix – parent – suffix

1. The Prefix: tells what are and when are the substituents.
 a. Substituent prefixes: parts that identify what substituents are located on the
main chain or ring.
b. Locants: numbers that tell where substituents are located on the main chain or
ring.
2. The parent part tells how many carbons and what and how many bonds are present. The
infix in the parent name tells what type of carbon-carbon bonds and how many of them are
present in the parent chain.

Infix Nature of Carbon-Carbon Bonds in the

Parent Chain
-an- All single bond
-en- One or more double bonds
-yn- One or more triple bonds

3. The suffix: tells the class of compounds to which the substance belongs.
Suffic Class of Compound
-e Hydrocarbon
-ol Alcohol
-al Aldehyde
-one Ketone
-oic acid Carboxylic acid

4. HYDROCARBONS
Organic compounds that contain only hydrogen and carbon atoms

a. ALKANES
 Have a general formula CnH2n+2, where n represents the number of C-atoms.
 This general formula shows a homologous series of carbon atoms. Each number in this
series differ from its immediate neighbor by methylene group, CH2, which is called
homologous.
 Contains single bond
 Also known as the paraffin series
 The C atoms are saturated with hydrogen atoms.

Nomenclature
IUPAC System of Naming Branched Alkanes

Brief History
 In earlier times, when few pure organic chemicals were known, new compounds were named at
the whim of their discoverer.
 Urea (CH4N2O) is a crystalline substance isolated from urine,
 morphine (C17H19NO3) is an analgesic (painkiller) named after Morpheus, the Greek god
of dreams.
 As the science of organic chemistry slowly grew in the 19th century, so too did the number of
known compounds and the need for a systematic method of naming them.
 The system of naming (nomenclature) we’ll use in this book is that devised by the International
Union of Pure and Applied Chemistry (IUPAC, usually spoken as eye-you-pac).
 A chemical name typically has four parts in the IUPAC system of nomenclature: prefix,
parent, locant, and suffix.
 The prefix specifi es the location and identity of various substituent groups in the molecule,
 the parent selects a main part of the molecule and tells how many carbon atoms are in that
part,
 the locant gives the location of the primary functional group, and the suffiidentifies the
primary x functional group.

Prefix Parent Locant Suffix

Where and what are How many Where is the

the substituents? carbons? What is the primary
primary
functional group?
functional group?
functional group?
STEP 1 Find the parent hydrocarbon.
a. Find the longest continuous carbon chain in the molecule and use the name of that chain as the
parent name. The longest chain may not always be obvious; you may have to “turn corners.”
CH2CH3

CH3CH2CH2CHCH3 Named as a substituted hexane

 b. If two chains of equal length are present, choose the one with the larger number of branch
points as the parent.

CH3 CH3

CH3 CH3CHCHCH2CH2CH3 CH3CH CHCH2CH2CH3

CH2CH3 CH2CH3

Named as a hexane with two substituents NOT as a hexane with one substituen

STEP 2 Number the atoms in the main chain.

Beginning at the end nearer the first branch point, number each carbon atom in the parent chain.

The first branch occurs at C3 in the proper system of numbering but at C4 in the improper system.

STEP 3 Identify and number the substituents.

Assign a number, called a locant, to each substituent to specify its point of attachment to the
parent chain. If there are two substituents on the same carbon, assign them both the same
number. There must always be as many numbers in the name as there are substituents.

STEP 4 Write the name as a single word.

Use hyphens to separate the various prefixes and commas to separate numbers. If two or more
different side chains are present, cite them in alphabetical order. If two or more identical side
chains are present, use the appropriate multiplier prefi xes di-, tri-, tetra-, and so forth. Don’t
use these prefi xes for alphabetizing, though. Full names for some examples follow:
For historical reasons, a few simple branched-chain alkyl groups also have
nonsystematic, common names, as noted in Figure 2.3.

Naming an Alkane
What is the IUPAC name of the following alkane?
Strategy :

The molecule has a chain of eight carbons (octane) with two methyl substituents. Numbering
from the end nearer the fi rst methyl substituent indicates that the methyls are at C2 and C6.

Drawing a Structure from a Name

Draw the structure of 3-isopropyl-2-methylhexane. Strategy First, look at the parent name
(hexane) and draw its carbon structure.

C-C-C-C-C-C Hexane

Next, find the substituents (3-isopropyl and 2-methyl), and place them on the proper carbons.
REFERENCES:

McMurry. (2011). Fundamentals of Organic Chemistry, 7th Edition. Retrieved from

https://gtu.ge/Agro-Lib/McMurry%20J.E.%20-
%20Fundamentals%20of%20Organic%20Chemistry,%207th%20ed.%20-%202010.pdf
The LibreTexts libraries. (2020). Nomenclature of Aldehydes & Ketones. Libretexts Chemistry.
Retrieved from
https://chem.libretexts.org/Bookshelves/Organic_Chemistry/Supplemental_Modules_(Orga
nic_Chemistry)/Aldehydes_and_Ketones/Nomenclature_of_Aldehydes_and_Ketones

The LibreTexts libraries. (2019). Condensed Structural and Line-Angle Formulas. Libretexts
Chemistry. Retrieved from
https://chem.libretexts.org/Courses/University_of_South_Carolina__Upstate/USC_Upstate
%3A_CHEM_U109_-
_Chemistry_of_Living_Things_%28Mueller%29/11%3A_Organic_Chemistry/11.03_Condens
ed_Structural_and_Line-Angle_Formulas

Xin Liu. IUPAC Naming of Organic Compounds with Functional Groups. Kwantlen Polytechnic
University. Retrieved from https://kpu.pressbooks.pub/organicchemistry/chapter/2-4-
naming-of-organic-compounds-with-functional-groups/