MSU-ISMP-GU-002.

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Effective Date: 7-DEC-2016

Activity No. 9

Formulas, Functional Groups and Nomenclature of Organic

Compounds

Formulas and Functional Groups

I- Introduction

Formulas of organic compounds are written in different ways and it is a prerequisite to students
who studies Organic Chemistry to be familiar with these formulas. When one would like to find an
information about a compound, one has to determine first its chemical formula. From the chemical
formula, the kinds of elements can be determined, their proportions, and the functional groups of the
compound. From a given formula, one can even predict the chemical property of the compound.

A chemical formula is a shortcut method of showing information about the chemical

proportions of atoms composing a particular chemical compound or molecule, using chemical element
symbols and numbers. Sometimes, these also includes symbols, such as parentheses, dashes, brackets,
commas, plus and minus signs. An organic compound can be written in different formulas. They are
molecular, empirical, structural, condensed and skeletal formula. A molecular formula simply shows
the number of each type of atom present. It tells you nothing about the bonding within the compound.
Empirical formula gives the simplest possible whole number ratio of all the different types of atoms
within the compound. Structural formula shows how atoms are arranged in the molecule. This means,
it shows all the bonds between atoms in a molecule. Condensed formula shows the order of atoms but
are written in a single line to save space and make it more convenient and faster to write out. And in
skeletal formula, the hydrogens are omittedand line ends or vertices represents carbons. Functional
groups and atoms aother than carbon and hydrogen are still shown. From the given formulas,
functional groups can be identified. Take note the maximum covalent bonds that the following atoms
can form with another atom are:
C – 4 covalent bonds O – 2 covalent bonds S – 2 covalent bonds
H – 1 covalent bond N – 3 covalent bonds Halogens such as F, Cl, Br, I – 1 covalent bond

Take note that for every 1 covalent bond formed by 2 atoms, it means that a pair of electrons is shared
by the two atoms.

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II- Objectives

At the end of this activity, you should be able to:

1. write the, molecular, empirical, structural, condensed and skeletal formula of organic compounds
2. classify the organic compounds based on the functional groups.

Nomenclature of Organic Compounds

I- Introduction
In studying organic chemistry, one of the first topics that one will encounter is the proper way
of naming organic compounds be it in IUPAC System or Systematic System. The primary function is
to ensure that a spoken or written chemical name leaves no doubt concerning which chemical
compound the name refers to. In addition, it is also of paramount importance that one knows the proper
way to write the formulas of the written names of organic compounds. Mastery in these subject matters
will lead to deeper understanding of the reactions of organic compounds with other substances.

Alkanes
Hydrocarbons are organic compounds composing only of the elements carbon and hydrogen.
They are alkanes, alkenes and alkynes. Alkanes (straight chain) or cycloalkanes (rings) are
hydrocarbons having only single bonds. These are also referred to as saturated hydrocarbons. Although
these hydrocarbons have no functional groups, they constitute the framework on which functional
groups are located in other classes of compounds, and provide an ideal starting point for studying and
naming organic compounds. The alkanes and cycloalkanes are also members of a larger class of
compounds referred to as aliphatic. Simply put, aliphatic compounds are compounds that do not
incorporate any aromatic rings in their molecular structure.

Table below lists the IUPAC names assigned to simple continuous-chain alkanes from C-1 to
C-10 and table 2 gives examples of cycloalkanes. A common "ane" suffix identifies these
compounds as alkanes and cylcoalkanes. The names methane through decane should be
memorized, since they constitute the root of many IUPAC names. The general formula for
alkane is CnH2n + 2 while cycloalkane is CnH2n where n is the number of carbons.

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Table 1: Simple alkanes

Name Molecular Condensed Structural Formula
Formula Formula
Methane CH4 CH4 CH4
Ethane C2H6 CH3CH3 CH3-CH3
Propane C3H8 CH3CH2CH3 CH3-CH2-CH3
Butane C4H10 CH3CH2CH2CH3 CH3-CH2-CH2-CH3
Pentane C5H12 CH3(CH2)3CH3 CH3-CH2-CH2-CH2-CH3
Hexane C6H14 CH3(CH2)4CH3 CH3-CH2-CH2-CH2-CH2-CH3
Heptane C7H16 CH3(CH2)5CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH3
Octane C8H18 CH3(CH2)6CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH3
Nonane C9H20 CH3(CH2)7CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3
Decane C10H22 CH3(CH2)8CH3 CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH3

Table 2: Cycloalkanes

Alkyl Groups
An alkyl is a functional group of an organic chemical that contains only carbon and hydrogen
atoms, which are arranged in a chain. They have general formula CnH2n+1. Alkyl groups usually appear
as substituent in other group of organic compounds usually branched organic compounds.

Table 1: First 10 Simple Alkyl Groups

Name Molecular Condensed Structural Formula
Formula Formula
Methyl CH3- CH3- CH43
Ethyl C2H5- CH3CH2- CH3-CH2-
Propyl C3H7- CH3CH2CH2- CH3-CH2-CH2-
Butyl C4H9- CH3CH2CH2CH2- CH3-CH2-CH2-CH2-
Pentane C5H11- CH3(CH2)3CH2- CH3-CH2-CH2-CH2-CH2-
Hexane C6H13- CH3(CH2)4CH2- CH3-CH2-CH2-CH2-CH2-CH2-
Heptane C7H15- CH3(CH2)5CH2- CH3-CH2-CH2-CH2-CH2-CH2-CH2-

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Octane C8H17- CH3(CH2)6CH2- CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-

Nonane C9H19- CH3(CH2)7CH2- CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-
Decane CH3-CH2-CH2-CH2-CH2-CH2-CH2-CH2-CH2-
C10H21- CH3(CH2)8CH2-
CH2-

Alkenes and Alkynes

Alkenes and alkynes are unsaturated aliphatic hydrocarbons. Alkenes and alkynes are hydrocarbons
which respectively have carbon-carbon double bond and carbon-carbon triple bond functional
groups, respectively.

This is the maximum H:C ratio for a given number of carbo

Alkane R–CH2–CH2–R CnH2n+2
atoms.

Each double bond reduces the number of hydrogen atoms

Alkene R–CH=CH–R CnH2n
2.

Alkyne R–C≡C–R CnH2n-2 Each triple bond reduces the number of hydrogen atoms b

IUPAC Rules for Alkene and Cycloalkene Nomenclature

1. The name follows the name of the alkane. The ene suffix (ending) indicates an alkene or
cycloalkene.
2. The longest chain chosen for the root name must include both carbon atoms of the double bond.
3. The root chain must be numbered from the end nearest a double bond carbon atom. If the
double bond is in the center of the chain, the nearest substituent rule is used to determine the
end where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the double bond is used as the
double bond locator. If more than one double bond is present the compound is named as a diene,
triene or equivalent prefix indicating the number of double bonds, and each double bond is
assigned a locator number.
5. In cycloalkenes the double bond carbons are assigned ring locations #1 and #2. Which of the
two is #1 may be determined by the nearest substituent rule.
6. Substituent groups containing double bonds are:
H2C=CH– Vinyl group
H2C=CH–CH2– Allyl group

Example:
CH3-CH=CH2 Propene
CH3-CH=CH-CH3 2-Butene
CH3-CH2-CH=CH-CH=CH2 1,3-Hexadiene

IUPAC Rules for Alkyne Nomenclature

1. The name follows the name of alkane. The yne suffix (ending) indicates an alkyne or
cycloalkyne.
2. The longest chain chosen for the root name must include both carbon atoms of the triple bond.
3. The root chain must be numbered from the end nearest a triple bond carbon atom. If the triple
bond is in the center of the chain, the nearest substituent rule is used to determine the end
where numbering starts.
4. The smaller of the two numbers designating the carbon atoms of the triple bond is used as the
triple bond locator.

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5. If several multiple bonds are present, each must be assigned a locator number. Double bonds
precede triple bonds in the IUPAC name, but the chain is numbered from the end nearest a
multiple bond, regardless of its nature.
6. Because the triple bond is linear, it can only be accommodated in rings larger than ten carbons.
In simple cycloalkynes the triple bond carbons are assigned ring locations #1 and #2. Which of
the two is #1 may be determined by the nearest substituent rule.
7. Substituent groups containing triple bonds are:
HC≡C– Ethynyl group
HC≡CH–CH2– Propargyl group
Example:
CH3-C≡CH Propyne
CH3-C≡C-CH3 2-Butyne
CH3-CH2-C≡C-C≡CH 1,3-Hexadiyne

Type of IUPAC Name Common Name

Compound
Alkanes 1. Find the longest continuous
carbon chain in the compound and
consider it as parent compound and
determine its name by changing the
yl of alkyl name to ane of alkane
name.
2. If there are substituent present,
number the carbon starting from the
end of the chain nearest to the
substituent.
3. Name the compound by naming
first the location of the substituent
on the main chain followed by a
hyphen(-) then the name of the
subsituent (such chloro for Cl,
fluoro for F, bromo for Br, iodo for
I, alkyl name of substituent)
followed by the parent alkane
name.
4. If the same substituent occurs
more than once in the compound, a
separate position number is given
for each, and the prefixes di for 2,
tri for 3, tetra for 4, penta for 5, and
so forth are used before the name of
the
substituent (example 2,4-
Dibromopentane for the compound
CH3CHBrCH2CHBrCH3). Take
note that the position of the
substituent are separated by a
comma.
5. If there are different kinds of
substituent, place the names of the
substituent in alphabetical order.
By convention, halogen
substituents are placed before alkyl
substituents. Again the carbon
numbers are separated by commas,
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and numbers are separated from

names by hyphens. Example: 2-
Bromo-3,3-dimethylpentane for the
compound
CH3
│
CH3CHBrCCH2CH3
│
CH3

Alkenes Name the parent compound using Name the parent compound using the
the longest continuous carbon chain longest continuous carbon chain
containing the double bond. containing the double bond. Change
Change ane ending of alkane name ane ending of alkane name to ylene.
to ene. The position of the double The position of the double bond/s
bond should be indicated for should be indicated for alkenes with
alkenes with four carbons or more. four carbons or more. Count the
Count the position of the carbon position of the carbon nearest to the
nearest to the double bond. double bond.

Example: CH2=CH2 Ethene Example: Ethane to Ethylene

Example: CH3CH=CHCH3 Example: CH3CH=CHCH3

(position 4 3 2 1 (position 4 3 2 1
of carbon) of carbon)

2-Butene or But-2-ene 2-Butylene or But-2-ylene

If substituents are present, just like , If substituents are present, just like
the position and name of the alkane the position and name of the
substituents will come ahead of the substituents will come ahead of the
parent name. parent name.

Example: CH3CH2CH2CCl=CH2 Example: CH3CH2CH2CCl=CH2

5 4 3 2 1 5 4 3 2 1
2-Chloro-1-Pentene or 2-Chloro-1-pentylene
2-Chloropent-1-ene or 2-Chloropent-1-ylene

Alkyne Name the parent compound using C ≡ C is called acetylene

the longest continuous carbon chain
containing the double bond. Change Name the Alkyl group attached to
ane ending of alkane name to yne, acetylene then the word acetylene
from butane and up the position of
triple bond should be indicated Example: CH3CH2C≡CH

Example: Ethane to Ethyne Ethyl acetylene

CH≡CH

Example: CH3CH2C≡CH
1-Butyne

If substituents are present, just like

alkane the position and name of the
substituents will come ahead of the
parent name.

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Example: CH3CH2CHClC≡CH
5 4 3 2 1
3-Chloro-1-Pentyne or
3-Chloropent-1-yne

Alkyl Halide Name the halogen such as fluoro, Name the alkyl group then the
or chloro, bromo, and iodo then the halogen ending in ide,
Haloalkanes alkane name.
Example: CH3CH2 – Cl
Example: CH3CH2 – Cl Ethyl chloride
Chloro ethane
Primary Start the name with amino (for NH2) Name the alkyl (R) group then
Amine then the alkane name of the alkyl continue the word amine
group (R).
Example: CH3 – NH2
Example: CH3 – NH2 Methylamine
Aminomethane
Secondary Start with N-then the alkyl (R) group Name the two R group ( in
Amine (with fewer carbon) attach to N then alphabetical order) then end with
amino and then alkane name of the amine
other R group

Example: CH3 – NH – CH2CH3

N-Methylaminoethane Example: CH3 – NH – CH2CH3
Ethylmethylamine

Tertiary Start with N,N-then the two R group Name the three R group then end
Amine (with fewer carbon) attach to N then with amine.
amino and then the alkane name of
the other R group (R with most
carbon atom).

Example: CH3
| Example:
CH3
CH3 – N– CH2CH3 |
N,N-Dimethylaminoethane CH3 – C– CH2CH3
Dimethylethylamine
Alcohols Change ane ending of alkane name Name the R group then the word
to ol. alcohol.

Example: CH3CH2 – OH Example: CH3CH2 – OH

Ethanol Ethyl alcohol
Phenols The position of OH group in phenols
is always in carbon 1 of the benzene
structure and counting is always
clockwise.

Write the position of the substituent

Carbon 2 and 5 are also called ortho
(o); 3 and 6 are also called meta (m);
and carbon 4 is para (p) followed by
a hypen then the name of substituent
such as fluoro, chloro, bromo, iodo
followed by the name phenol.

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Example: F

2-Fluorophenol or
o-Fluorophenol

Ethers Name the R group (with fewer Name the two R groups
carbon) ending in oxy then the alphabetically then the word ether.
alkane name of the other R group.

Example: CH3CH2 – O – CH3 Example: CH3CH2 – O – CH3

Methoxyethane Ethylmethyl ether

Aldehydes Change ane ending of alkane name Names ends in aldehyde,

to al. O
O ‖
‖ Example: H – C - H
Example: CH3 – C - H Formaldehyde
Ethanal
O
‖
Example: CH3 – C - H
Acetaldehyde

O
‖
Example: CH3CH2 – C - H
Propionaldehyde
O
‖
Example: CH3CH2CH2 – C - H
Butyraldehyde
O
‖
Example: CH3CH2CH2CH2 – C - H
Valeraldehyde

Example:CH3CH2CH2CH2CH2–C-H
Capraldehyde

Example:
Benzaldehyde
Ketones Change ane ending of alkane name Name the two R groups then the
to one. Number carbon nearest to word ketone, except
C=O. Indicate carbon number of O
C=O when naming, except ketones ‖
with 3 and 4 carbons. CH3 – C – CH3 which is named
acetone
O
‖ O
Example: CH3CH2CH2 – C – CH3 ‖
5 4 3 2 1 Example: CH3CH2CH2 – C – CH3
2- Pentanone Methylpropyl ketone

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Carboxylic Change e ending of alkane name to Change the aldehyde name by

acid oic acid. ending in ic and then the word
acid. Add n- before the name when
the carboxylic acid has 4 carbons
and up.
O
‖ O
Example: CH3 – C - OH ‖
Ethanoic acid Example: CH3 – C - OH
Acetic acid

Carboxylic Name the R group attached to Name the R group attached to

Ester terminal O of the -COO- group and terminal O of the -COO- group and
the other R group including in the the other R group including in the
count the carbon in -COO- group count the carbon in the -COO-
ending in oate. group similar to aldehydes’
common name but this time ending
in ate.
Example: O
‖ Example: O
CH3 – C – O – CH2CH3 ‖
Ethyl ethanoate CH3 – C – O – CH2CH3
Ethyl acetate

II- Objectives
At the end of this activity, you should be able to:
1. write the IUPAC and common names of organic compounds and writing the formulas.

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DATA AND ANSWER SHEET NO. 9

Name: _________________________ Yr/Sec: ____________________ Date Performed: ___________

Course: ________________________ Group Number: _____________ Date Submitted: ___________
Class Schedule: _________________ Lab. Instructor: _____________ Score: ___________

Formulas, Functional Groups and Nomenclature of Organic Compounds

Supply the missing information in Tables A and B

Table A
Name of Compound Molecular Empirical Condensed Line Skeletal Functional
Formula Formula Formula Structural Formula Group
Formula
1. Hexane C6H14

2. Ethene C2H4

3. Ethyne C2H2

4. Propanol CH3CH2CH2OH

5. Butanal C4H8O

6. Butanone C4H8O

7. Propanoic Acid CH3CH2COOH

8. Ethylmethanoate CH3CH2COOCH3

9. Propanamine CH3CH2CH2NH2

10. Methoxymethane CH3OCH3

Table B
Type of General Molecular Skeletal Formula
Structure
Compound Formula Formula

C6H12

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Table C. Give the IUPAC and Common Name the following organic compounds.

1. CH3CH2CH2CH2COOCH2CH2CH2CH3 2. CH3CH2CH2CH2CH2COCH2CH2CH2CH3

_________________________________ ________________________________________

_________________________________ ________________________________________

3. CH3CH2 CH2CH2CHOHCH3 4. CH3CH2CH2 –O– CH2CH2CH2CH3

_________________________________ _____________________________________

__________________________________ ______________________________________

5. CH3CH2CH2CH2CH2CH2CH2COOH 6. CH3C ≡CCH2CH3

___________________________________ ____________________________________

___________________________________ ____________________________________

7. CH3CH2CH2CH2CH2NH2 8. CH3CH2CH=CHCH2CH2CH3

___________________________________ ____________________________________

___________________________________ ____________________________________

9. CH3CH2CH2CH2CH2CHO 10. CH3CH2CH2CH2CH2NHCH2CH2CH3

___________________________________ ___________________________________

___________________________________ ___________________________________

Conclusion

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