SEd Sci 221- ORGANIC CHEMISTRY

Chapter 3- Functional Groups and the Types of Organic Compounds

Introduction
This chapter is focused on the functional groups and the types of organic
compounds. You were previously introduced to several structural units that chemist
use to classify organic compounds and predict their reactivities. These functional
groups, which determine the chemical reactivity of a molecule under a given
conditions, can consist of a single atom such as Cl or group of atoms such as CO 2H.
the major families of organic compounds are characterized by their functional
groups.
In figure 1 and 2 summarizes five families introduced I the earlier chapters,
give examples of compounds that contain each functional group, and lists the suffix
or prefix used in the systematic nomenclature of compounds that contain each
functional group.
Learning Outcomes:
In this chapter, you are expected to:
1. Discuss the major types of organic compounds and identify important
functional groups;
2. Distinguish between the different hydrocarbon functional groups;

Learning Contents:
This chapter contains the following lessons for you to be able to meet the
expected learning outcomes:
1. Functional groups
2. Types of organic compounds
3. Different hydrocarbon functional groups
Functional Groups
In organic chemistry, a functional group is a substituent or moiety in
a molecule that causes the molecule's characteristic chemical reactions. The same
functional group will undergo the same or similar chemical reactions regardless of
the rest of the molecule's composition. This enables systematic prediction of
chemical reactions and behavior of chemical compounds and the design of chemical
synthesis.
The reactivity of a functional group can be modified by other functional groups
nearby. Functional group interconversion can be used in retrosynthetic analysis to
plan organic synthesis.
A functional group is a group of atoms in a molecule with distinctive chemical
properties, regardless of the other atoms in the molecule. The atoms in a functional

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group are linked to each other and to the rest of the molecule by covalent bonds. For
repeating units of polymers, functional groups attach to their nonpolar core
of carbon atoms and thus add chemical character to carbon chains. Functional
groups can also be charged, e.g. in carboxylate salts (–COO−), which turns the
molecule into a polyatomic ion or a complex ion. Functional groups binding to a
central atom in a coordination complex are called ligands. Complexation
and solvation are also caused by specific interactions of functional groups. In the
common rule of thumb "like dissolves like", it is the shared or mutually well-
interacting functional groups which give rise to solubility.
Functional groups also play an important part in organic compound nomenclature;
combining the names of the functional groups with the names of the parent alkanes
provides a way to distinguish compounds. The atoms of a functional group are linked
together and to the rest of the compound by covalent bonds.

Why are functional groups important?

The main reason is that they form the fundamental of an organic molecule,
Functional groups are important.
Explanation:

Just like bricks, cement etc are the most important constituencies to build a house,
Just like that in the sphere of Organic chemistry the presence of Functional groups is
also important.
The functional groups make a molecule special deciding on its reactivity and how it
interacts with other molecules.

Functional groups determine the following things of a molecule:

=>Its melting and boiling point
=>The stability of the molecule
=>The reactivity of the molecule
=>The polarity of the molecule.

These are only some of the basis chemical properties and physical properties which
can be identified through the presence of a functional group in the organic molecule
chain.
The molecules are also grouped on the basis of their functional groups as molecules
of the same functional group are tend to show the same properties and different vice
versa.
Some important functional groups are:

Alcohol= OL
Ketone= O
Carboxylic acid= COOH etc..

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 Figure 1 below, shows the classes of organic compounds

Hydrocarbons
Hydrocarbons are a class of molecule that is defined by functional groups
called hydrocarbyls that contain only carbon and hydrogen, but vary in the number
and order of double bonds. Each one differs in type (and scope) of reactivity.

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 There are also a large number of branched or ring alkanes that have specific
names, e.g., tert-butyl, bornyl, cyclohexyl, etc. Hydrocarbons may form charged
structures: positively charged carbocations or negative carbanions. Carbocations are
often named -um. Examples are tropylium and triphenylmethyl cations and
the cyclopentadienyl anion.

Chemica Structural
Group Formula Prefix Suffix Example
l class Formula

Alkane Alkyl R(CH2)nH alkyl- -ane

Ethane

Alkene Alkenyl R2C=CR2 alkenyl- -ene

Ethylene
(Ethene)

Alkyny alkynyl
Alkyne RC≡CR' -yne Acetylene
l -
(Ethyne)

-
Benzene RC6H5
Phenyl phenyl- benzen
derivative RPh
e

Cumene
(Isopropylbenzene)

Groups containing halogen

Haloalkanes are a class of molecule that is defined by a carbon–halogen bond. This
bond can be relatively weak (in the case of an iodoalkane) or quite stable (as in the
case of a fluoroalkane). In general, with the exception of fluorinated compounds,

46
haloalkanes readily undergo nucleophilic substitution reactions or elimination
reactions. The substitution on the carbon, the acidity of an adjacent proton, the
solvent conditions, etc. all can influence the outcome of the reactivity.

Chemical Formul Structural

Group Prefix Suffix Example
class a Formula

haloalkane halo RX halo- alkyl halide Chloroethane

(Ethyl chloride)

fluoroalkane fluoro RF fluoro- alkyl fluoride

Fluoromethane
(Methyl
fluoride)

chloroalkane chloro RCl chloro- alkyl chloride

Chloromethane
(Methyl
chloride)

alkyl bromid
bromoalkane bromo RBr bromo-
e

Bromomethane
(Methyl
bromide)

iodoalkane iodo RI iodo- alkyl iodide

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 Iodomethane
(Methyl iodide)

Groups containing oxygen

Compounds that contain C-O bonds each possess differing reactivity based
upon the location and hybridization of the C-O bond, owing to the electron-
withdrawing effect of sp-hybridized oxygen (carbonyl groups) and the donating
effects of sp2-hybridized oxygen (alcohol groups).

Stru
Ch
ctur
emi Gr
Form al Prefi Exa
cal ou Suffix
ula For x mple
cla p
mul
ss
a

Alc Hy
hydr
oho dro ROH -ol
oxy-
l xyl
Meth
anol

-oyl- 
(-
Car COR Butan
Ket RCO one
bon ') -one
one R' (Met
yl or
oxo- hyl
(=O) ethyl
keton
e)

Ald Ald RCH form -al

ehy ehy O yl- (-
de de COH
)
or
oxo- Aceta
(=O) ldehy
de
(Etha

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 nal)

carb
onofl
uorid
-oyl fl
oyl-
uorid
carb
e
onoc
-oyl c Acety
Ac Hal hlori
hlorid l
yl ofo RCO doyl-
e chlori
hali rm X carb
-oyl b de
de yl onob
romid (Etha
romi
e noyl
doyl-
-oyl io chlor
carb
dide ide)
onoi
odid
oyl-

Triph
Car (alko osgen
Car bon xyca alkyl c e
ROC
bon ate rbon arbon (bis(t
OOR'
ate este yl)ox ate richl
r y- orom
ethyl)
carbo
nate)

Sodiu
Car Car m
box box RCO carb acetat
-oate
ylat ylat O− oxy- e
e e (Sodi
um
ethan
oate)

Car
box Car
RCO carb -oic a
ylic box Aceti
OH oxy- cid
aci yl c acid
d (Etha
noic
acid)

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 alka
noyl
Ethyl
Car oxy-
alkyl butyr
Est boa RCO or
alkano ate
er lko OR' alko
ate (Ethy
xy xyca
l
rbon
butan
yl
oate)

Hy
Hy alkyl 
dro hydr
dro ROO hydro tert-
per oper
per H peroxi Butyl
oxi oxy- hydro
oxy de
de perox
ide

Per alkyl  Di-

Per ROO pero
oxi peroxi tert-
oxy R' xy-
de de butyl
perox
ide

Dieth
Eth Eth alko alkyl e yl
ROR' ether
er er xy- ther
(Etho
xyeth
ane)
He He -al
R2CH alko
mia mia alkyl 
(OR1) xy -
cet cet hemia
(OH) ol
al al cetal
RC(O -one
He He alko
Rʺ) alkyl 
mik mik xy -
(OH) hemik
etal etal ol
R' etal
-al
RCH(
Ac Ac dialk dialky
OR')
etal etal oxy- l acet
(OR")
al
Ket Ket
al ( al ( RC(O
-one
or  or  R") dialk
dialky
Ac Ac (OR oxy-
l ketal
etal etal ‴)R'
) )
RC(O
Ort Ort
R') trialk
hoe hoe
(OR") oxy-
ster ster
(OR‴)

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 Het 1,2-
ero Me Meth
meth
cyc thyl (– - ylene
ylen
le ene OCH2 dioxol dioxy
edio
(if dio O–) e benze
xy-
cyc xy ne
lic) (1,3-
Benz
odiox
ole)

Ort Ort
hoc hoc C(OR tetraa
arb arb ) tetral lkyl or
ona ona (OR') koxy thoca
te te (OR") - rbona Tetra
este este (OR‴) te meth
r r oxym
ethan
e
Org
ani Car
c box R1(C
aci ylic O)O( anhyd Butyr
d anh CO)R ride ic
anh ydr 2 anhyd
ydr ide ride
ide

Groups containing nitrogen

Compounds that contain nitrogen in this category may contain C-O bonds,
such as in the case of amides.

Chemical Structural
Group Formula Prefix Suffix Example
class Formula

carboxami
do-
Carboxami
Amide RCONR'R" or -amide
de
carbamoyl Acetamide
- (Ethanamide)

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 Primary
RNH2 amino- -amine
amine
Methylamine
(Methanamine)

Secondary
R'R"NH amino- -amine
amine
Dimethylamine

Amines

Tertiary
R3 N amino- -amine
amine
Trimethylamine

4° -
ammonium R4N+ ammonio- ammoniu
ion m
Choline

Imine
Primary
RC(=NH)R' imino- -imine
ketimine

Secondary
imino- -imine
ketimine

Primary RC(=NH)H imino- -imine

aldimine

Ethanimine

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 Secondary
RC(=NR')H imino- -imine
aldimine

Imide Imide (RCO)2NR' imido- -imide

Succinimide
(Pyrrolidine-2,5-dione)

alkyl azi
Azide Azide RN3 azido-
de

Phenyl azide
(Azidobenzene)

Azo Azo
RN2R' azo- -diazene Methyl orange
compound (Diimide)
(p-dimethylamino-

azobenzenesulfonic acid)

alkyl cya
Cyanate ROCN cyanato-
nate
Methyl cyanate
Cyanates

isocyanato alkyl iso
Isocyanate RNCO
- cyanate
Methyl isocyanate

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 nitrooxy-, alkyl nit
Nitrate Nitrate RONO2
nitroxy- rate
Amyl nitrate
(1-nitrooxypentane)

alkanenit
rile
Nitrile RCN cyano-
alkyl cya
nide Benzonitrile
Nitrile (Phenyl cyanide)
alkaneiso
nitrile
Isonitrile RNC isocyano-
alkyl iso Methyl isocyanide
cyanide

nitrosooxy alkyl nit
Nitrite Nitrosooxy RONO
- rite Isoamyl nitrite
(3-methyl-1-
nitrosooxybutane)

Nitro
Nitro RNO2 nitro-  
compound
Nitromethane

Nitroso nitroso-
Nitroso RNO  
compound (Nitrosyl-)
Nitrosobenzene

Oxime Oxime RCH=NOH   Oxime

Acetone oxime
(2-Propanone oxime)

4-pyridyl
(pyridin-4-
yl)
3-pyridyl
Pyridine
Pyridyl RC5H4N (pyridin-3- -pyridine
derivative
yl)
Nicotine
2-pyridyl
(pyridin-2-
yl)

(- -
Carbamat
Carbamate RO(C=O)NR2 carbamoyl carbamat Chlorpropham
e ester
)oxy- e (Isopropyl (3-
chlorophenyl)carbamate)

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Carboxylic Acid Derivatives

The functional groups at the heart of this chapter are called carboxylic

acid derivatives: they include carboxylic acids themselves, carboxylates
(deprotonated carboxylic acids), amides, esters, thioesters, and acyl phosphates.

Cyclic esters and amides are referred to as lactones and lactams, respectively.

Carboxylic acid any hydrides and acid chlorides, which also fall under the carboxylic
acid derivative category, are not generally found in biomolecules but are useful intermediates
in laboratory synthesis. They are discussed in a section on laboratory reactions at the end of
this chapter.

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 Carboxylic acid derivatives can be distinguished from aldehydes and
ketones by the presence of a group containing an electronegative heteroatom -
usually oxygen, nitrogen, or sulfur – bonded directly to the carbonyl carbon.
You can think of a carboxylic acid derivative as having two sides. One side is
the acyl group, which is the carbonyl plus the attached alkyl (R) group. In the
specific cases where R is a hydrogen or methyl, chemists use the terms formyl
and acetyl group, respectively. One the other side is the heteroatom-linked
group: in this text, we will sometimes refer to this component as the ‘acyl X'
group (this, however, is not a standard term in organic chemistry).

Notice that the acyl X groups are simply deprotonated forms of other
functional groups linked to the acyl group: in an amide, for example, the acyl X
group is an amine, while in an ester the acyl X group is an alcohol.

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Fatty acid' molecules such as stearate are carboxylates with long carbon chains for
acyl groups.

The aromas of many fruits come from small ester-containing molecules:

57
The 'peptide bonds' that link amino acids together in proteins are amides.

Acetyl-Coenzyme A, a very important two carbon (acetyl group) 'building block'

molecule in metabolism, is characterized by reactions at its thioester functional
group:

58
Teaching and Learning Activities:
Activity 1:

Draw the structures indicated:

a. compound A after is has been acetylated (ie. an acetyl group added)

b. compound B after it has been formylated
c. compound C after it has been formylated
d. Compound D after it has been acetylated

Recommended learning materials and resources for supplementary reading:

The recommended learning materials and resources in this chapter include the URL
of the resources from the Internet (PDF, youtube, slideshare, etc.)

Flexible Teaching Learning Modality (FTLM):

This chapter adopts the synchronous and asynchronous learning modalities for you
to have better access and learning of the lessons. This may include google classroom,
moodle, schoology, edmodo, Podcast, printed materials and other resources depending on
your needs and capacity to use the material.

Assessment Task

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Name all carboxylic acid derivative groups in the molecules below.

References:
Book:
Carey, Francis A. Organic Chemistry. University of Virginia 3 rd Edition ©1996, The McGraw-
Hill Companies, Inc.
Internet:
https://chem.libretexts.org/Under_Construction/Purgatory/Book
%3A_Organic_Chemistry_with_a_Biological_Emphasis_(Soderberg)

Organic Chemistry With a Biological Emphasis by Tim Soderberg (University of Minnesota,

Morris)

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