UNIT 3: INTRODUCTION TO ORGANIC MOLECULES AND FUNCTIONAL

GROUPS

Objectives:

When the students have completed this lesson, the students should be able
to:

 Identify the functional groups

 Familiarize with the structures of functional groups
 Recognize the common functional groups and understand their
importance

Unit 3 Introduction to Organic Molecules and Functional Groups 49 Arranged by: Janet A. Dungog
Functional Groups

In addition to strong C - C and C - H bonds, organic molecules may have other structural features as well.
Although over 20 million organic compounds are currently known, only a limited number of common
structural features, called functional groups, are found in these molecules.

Characteristic Features of a Functional Group

1. A functional group is an atom or a group of atoms with characteristic chemical and physical
properties.

2. A functional group contains a heteroatom, a multiple bond, or sometimes both a heteroatom and a
multiple bond.

3. A functional group determines a molecule’s shape, properties, and the type of reactions it
undergoes. It is the reactive part of the molecule.

4. A functional group behaves the same whether it is bonded to a carbon backbone having as few as
two or as many as 20 carbons.
 For this reason, we often abbreviate the carbon and hydrogen portion of the molecule by a
capital letter R, and draw the R bonded to a particular functional group.

R Functional Group

carbon backbone ...... bonded ...... a particular functional group

Example:

H H hydroxyl
carbon
group
backbone H C C O H

H H

ethanol

The most common functional groups can be subdivided into three types:

hydrocarbons compounds containing a single compounds containing a C=O

bond to a heteroatom group

Unit 3 Introduction to Organic Molecules and Functional Groups 50 Arranged by: Janet A. Dungog
Why do heteroatoms and π bonds confer reactivity on a particular molecule?

Heteroatoms have lone pairs and create electron- π bonds are easily broken in chemical reactions. A
deficient sites on carbon. π bond makes a molecule a base and a
nucleophile.
The lone pairs make O
a base and a nucleophile. The pi bond makes a compound
a base and a nucleophile.

C O C C

electron-deficient C
The pi bond is easily broken.

Hydrocarbons
Hydrocarbons are compounds made up of only the elements carbon and hydrogen. They may be aliphatic
or aromatic.

1. Aliphatic hydrocarbons can be subdivided into three subgroups.

 Alkanes have only C – C σ bonds and no functional group. Ethane, CH3CH3, is a simple alkane.
 Alkenes have a C – C double bond as a functional group. Ethylene, CH2–– CH2, is a simple alkene.
 Alkynes have a C – C triple bond as a functional group. Acetylene, HCCH, is a simple alkyne.

2. Aromatic hydrocarbons.
This class of hydrocarbons was so named because many of the earliest known aromatic compounds had
strong, characteristic odors.
The simplest aromatic hydrocarbon is benzene. The six-membered ring and three π bonds of benzene
comprise a single functional group. Benzene is a component of the BTX mixture (B for benzene) added to
gasoline to boost octane ratings.

When a benzene ring is bonded to another group, it is called a phenyl group. In phenylcyclohexane, for
example, a phenyl group is bonded to the six-membered cyclohexane ring.

Unit 3 Introduction to Organic Molecules and Functional Groups 51 Arranged by: Janet A. Dungog
The table below summarizes the four different types of hydrocarbons.
Hydrocarbons

Type of Compound General Structure Example Functional Group

Alkane R-H CH3CH3 ----

Alkene H H
C C
C C double
H H

Alkyne C C H C C H triple

Aromatic compound
phenyl

Compounds Containing C–Z  Bonds

Several types of functional groups that contain C – Z  bonds are listed in the table below.

Type of General Structure Example 3-D Structure Functional Group

Compound

Alkyl halide R X CH3 Br -X

( X = F , Cl, Br, I) halo group

Alcohol CH3 OH CH3 OH -OH

hydroxy group

Ether R O R CH3 O CH3

-OR
alkoxy group

Amine CH3 NH2

-NH2
R NH2
amino group
or R 2NH or R 3N

Thiol R SH CH3 S H -SH

mercapto group

Sulfide R S R CH3 S CH3 -SR

alkylthio

Unit 3 Introduction to Organic Molecules and Functional Groups 52 Arranged by: Janet A. Dungog
The Electronegativity of Z

1. The electronegative heteroatom Z creates a polar bond, making carbon electron deficient.

C Z lone pair

electron-deficient C

2. The lone pairs on Z are available for reaction with protons and other electrophiles, especially when Z
= N or O.

Examples of Compounds Containing C–Z  Bonds

Several simple compounds in this category are widely used.

An alkyl halide used as a local anesthetic.

Cl
Chloroethane quickly evaporates when sprayed on a wound,
chloroethane causing a cooling sensation that numbs the site of an injury

O
It is the first common general anesthetic.
CH3CH2 CH2CH3

diethyl ether

O
OH
O O
H
O
O

hemibrevetoxin B

Compounds Containing a C=O Bonds

Unit 3 Introduction to Organic Molecules and Functional Groups 53 Arranged by: Janet A. Dungog
The C=O

1. The polar C – O bond makes the carbonyl carbon an electrophile, while the lone pairs on O allow it to
react as a nucleophile and base.

2. The carbonyl group also contains a  bond that is more easily broken than a C – O  bond.

Many different types of functional groups possess a C – O double bond (a carbonyl group), as shown below.

Type of General Structure Example 3-D Structure Functional

Compound Group

Aldehyde O O C=O
C C carbonyl group
R H CH3 H

Ketone O O C=O
C C carbonyl group
R R' CH3 CH3

Carboxylic acid O O -COOH

C C carboxy group
R OH CH3 OH

Ester O O

C
-COOR
C
R OR CH3 OCH3

Amide O O -CONH2, -
CONHR,
C H ( or R ) C
R N CH3 NH2 or
-CONR2
H ( or R )

Acid chloride O O

C
-COCl
C Cl
R Cl CH3

Unit 3 Introduction to Organic Molecules and Functional Groups 54 Arranged by: Janet A. Dungog
Examples of Compounds Containing a C=O Bonds
Atenolol and donepezil are examples of useful drugs that contain a variety of functional groups.

aromatic ring

ether
H2N
Atenolol is a a blocker, a group
O of drugs used to treat
amide O N hypertension.
H
OH amine
atenolol
( used to treat high blood pressure)

alcohol

ketone
aromatic O
ring
Donepezil, sold under the trade
aromatic
ring
name Aricept, is used to treat
CH3O N
mild to moderate dementia
ether associated with Alzheimer's
CH3O disease.
amine
donepezil
( used to treat Alzheimer's disease)

The importance of a functional group cannot be overstated. A functional group determines all the
following properties of a molecule:

bonding and shape nomenclature chemical reactivity

physical properties type and strength of intermolecular forces

Exercise

1. Classify each of the following compounds as an alkane, alkene, alkyne, alcohol, aldehyde, amine, and
so forth.

( ) ( ) CH3 C CH O
7 12
sex attractant of the common housefly H

OH OH O

obtained from oil of cloves

Unit 3 Introduction to Organic Molecules and Functional Groups 55 Arranged by: Janet A. Dungog
2. Oseltamivir (trade name Tamiflu), the most effective antiviral drug against avian influenza currently
available, can be prepared in 10 steps from shikimic acid. Identify the functional groups in Tamiflu and
shikimic acid.

O CO2CH2CH3
HO CO2H
O
10 steps

HO N
H
OH NH2

shikimic acid Tamiflu

3. Identify all of the functional groups in Crixivan, an important drug in the treatment of AIDS.

N OH C 6H5
H H OH
N NH
N H
H
O
HN O

C( CH3) 3

4. Identify all of the functional groups in the following molecule.

O O OH
O

N O
H O
OH H
HO O
O
O

5. Draw the structure of a compound fitting each description:

An aldehyde with molecular formula C4H8O A carboxylic acid with molecular formula C4H8O2

A ketone with molecular formula C4H8O2 An ester with molecular formula C4H8O2

Unit 3 Introduction to Organic Molecules and Functional Groups 56 Arranged by: Janet A. Dungog
6. The compounds, whose structures are shown below, incorporate a variety of functional groups. The
questions ask you to identify which compounds have a specific functional group. For each compound
that has the designated group, enter the appropriate number(s) in the answer box. The aromatic rings
should not be counted as double bonds.

CH2
O
CH3

CH3
H3C CH2 N
1. limonene 2. muscone 3. nicotine

O
CH3

OH
OH H3C
O
O
HO N
H3C O
H
H3C CH3
4. aspirin 5. geraniol 6. acetaminophen

1. Which have carbon-carbon double bonds?

2. Which have a ketone carbonyl group?

3. Which have an aldehyde carbonyl group?

4. Which have amino groups?

5. Which have aromatic rings?

6. Which have a hydroxyl group?

7. Which have ether groups?

8. Which have an ester group?

9. Which have an amide group?

10. Which have a carboxylic acid group?

Unit 3 Introduction to Organic Molecules and Functional Groups 57 Arranged by: Janet A. Dungog
6. The compounds, whose structures are shown below, are all natural substances from a variety of
sources. The questions concern the functional groups that are present in these compounds, and
require you to enter appropriate letters (A through H) in the answer box for each question.

O N
H3C

O O
CO2H
N HO
O
CH3
CH2
A nepe talactone O
( essence of catnip) B strychnine ( a plant alkaloid) C hirsutic acid ( a fungal me ta bolite )

O
O

H H
H Br
H Br Cl
O H
D progesterone E helminthospora l ( E ) -1,6-dibromo-2,7-dichloro-3,7-dimethyloct-3-ene
( a progestin hormone) ( a fungal toxin) ( from red algae)

1. Which compounds have a carbon-carbon triple bond?

2. Which have an aldehyde or ketone carbonyl group?

3. Which have an amino group?

4. Which have a carboxylic acid group?

5. Which have an epoxide group?

6. Which have an ether group?

7. Which have an ester group?

8. Which have a hydroxyl group?

9. Which have an aromatic ring?

Unit 3 Introduction to Organic Molecules and Functional Groups 58 Arranged by: Janet A. Dungog