ORGANIC

COMPOUNDS
The unique properties of the CARBON
atom will help one understand the
properties of organic compounds.
■ Form covalent bonds
■ Share electrons with may different elements
(H, O, N, and C)
■ Has 4 valence electrons and therefore can
form 4 stable covalent bonds
■ Its ability to bond with other carbon atoms to
form chains of endless variety. (property
called CATENATION) – most unique property
■ Can form a variety of geometrical structures
(straight chains, branched chains, cyclics, sheeets, and spheres)
 Hydrocarbon

Aliphatic Cyclic
(Open Chain) (Closed Chain)

Unsaturated
Saturated Alicyclic Aromatic
(ALKANE)
CnH2n+2 ALKENE ALKYNE
(Cycloalkane) (Benzene)
(Olefins)
CnH2n Cn H2n-2
There are ways in which we can represent the bonding
of hydrocarbons

CONDENSED STRUCTURAL
EXPANDED/COMPLETE C4H10 FORMULA
STRUCTURAL
FORMULA MOLECULAR FORMULA

BUTANE

C-C-C-C

LINE FORM CARBON SKELETAL FORM

The classification of organic compounds is
based on the presence of the group of
atoms called FUNCTIONAL GROUPS
■ HYDROCARBONS
■ ETHERS
■ ALCOHOLS
■ ALDEHYDES
■ KETONES
■ CARBOXYLIC ACIS
■ ESTERS
■ AMINES
Note: Compounds containing similar functional groups
often undergo similar reactions.
 Compounds that have the same molecular
formula but have different structures are
called ISOMERS.

CH3CH2CH2CH2CH2CH3

CH3CH(CH3)CH2CH2CH3
CH3CH(CH3)CH2CH2CH3 The 5
ISOMERS
Of C6H14

CH3CH2CH(CH3)CH2CH3 CH3CH(CH3) CH(CH3)CH3

Constitutional isomers ARE COMPOUNDS WHICH HAVE THE
SAME CHEMICAL FORMULA BUT DIFFERENT STRUCTURAL
FORMULA.

C4H10

MOLECULAR FORMULA
BUTANE

EXPANDED/COMPLETE
STRUCTURAL
FORMULA

BUTANE 2 METHYL PROPANE

Numerical Roots for Carbon Chains and Branches
PREFIX + ROOT + SUFFIX
Roots Number of C
atoms
meth- 1
eth- 2
prop- 3
but- 4
pent-
5
hex-
6
hept-
oct- 7
non- 8
9
dec- 10
undec- 11
pentadec- 15
triacont- 30
There are a few common branched substituents
you should MEMORIZE.
All carbons attached to other elements via all
single bonds have molecular orbitals that are
HYBRIDIZED.
■ Each sp3 hybridized carbon has four sp3 orbitals
■ The bond between the two carbons is made up of
the overlap of the two sp3 orbitals. This type of
head-on overlap forms the sigma ( ) bond.
■ In general, all single bonds are considered
SIGMA bonds. (All ALKANES are all SIGMA
bonds)
■ All carbons with a double bond has a molecular
orbital of sp2.
■ All carbons with a triple bond = one sp and 2 p
orbital
The three types of hydrocarbons (Alkanes,
Alkenes and Alkynes) have the following
properties:

■ Generally non-polar
■ Dominant intermolecular force (IMF) : LONDON
FORCES

The longer alkenes & alkynes have stronger IMF

and exhibit higher boiling and melting points
Simple rules to follow in naming hydrocarbons

1) Identify the longest carbon chain. This chain is called

the parent chain.
2) Identify all of the substituents (groups appending from
the parent chain).
3) Number the carbons of the parent chain from the end
that gives the substituents the lowest numbers. When
comparing a series of numbers, the series that is the
"lowest" is the one which contains the lowest number
at the occasion of the first difference. If two or more
side chains are in equivalent positions, assign the
lowest number to the one which will come first in the
name.
Simple rules to follow in naming hydrocarbons

4) If the same substituent occurs more than once, the

location of each point on which the substituent occurs
is given. In addition, the number of times the
substituent group occurs is indicated by a prefix (di,
tri, tetra, etc.).
5) If there are two or more different substituents they are
listed in alphabetical order using the base name
(ignore the prefixes). The only prefix which is used
when putting the substituents in alphabetical order
is iso as in isopropyl or isobutyl. The prefixes sec-
and tert- are not used in determining alphabetical
order except when compared with each other.
 Simple rules to follow in naming hydrocarbons

6) If chains of equal length are competing for selection as the parent

chain, then the choice goes in series to:
a) the chain which has the greatest number of side chains.
b) the chain whose substituents have the lowest- numbers
c) the chain having the greatest number of carbon atoms in the smaller
side chain.
d) the chain having the least branched side chains.

7) A cyclic (ring) hydrocarbon is designated by the prefix cyclo-which

appears directly in front of the base name.
■ In summary, the name of the compound is written out with the
substituents in alphabetical order followed by the base name (derived
from the number of carbons in the parent chain). Commas are used
between numbers and dashes are used between letters and
numbers. There are no spaces in the name.
 Simple rules to follow in naming hydrocarbons

5) If there are two or more different substituents they are

listed in alphabetical order using the base name
(ignore the prefixes). The only prefix which is used
when putting the substituents in alphabetical order
is iso as in isopropyl or isobutyl. The prefixes sec-
and tert- are not used in determining alphabetical
order except when compared with each other.
6) If chains of equal length are competing for selection
as the parent chain, then the choice goes in series to:
a) the chain which has the greatest number of side
chains.
b) the chain whose substituents have the lowest-
numbers.
c) the chain having the greatest number of carbon
atoms in the smaller side chain.
d)the chain having the least branched side chains.
Draw the complete (expanded), condensed
structural and line structural diagrams of the
following organic compounds

1) 3, 3-dimethyl hexane
2) 4-butyl-6-ethyl-2, 5-dimethyl decane
3) 3-ethyl-4-methly-1-hexene
4) 3-methyl-1-pentene
5) 4, 5-dimethyl-2-hexyne
6) 2,5,7-trimethyl-3-octyne
When a functional group is present, the compound is
generally called a HYDROCARBON DERIVATIVE.
Type of Hydrocarbon General Formula Functional group
Derivative
Alcohol R-OH hydroxyl

Ether R-O-R’ Ether (alkoxyl)

Aldehyde RC(O)H carbonyl

Ketone RC(O)R’ carbonyl

Carboxylic acid RCOOH carbonyl

Amine R-NH2 amino

Ester RC(O)OR’ ester

Amide RC(O)-NH2 amido

Halocarbon R-X halogen

 ALCOHOLS are organic compounds that contain the
hydroxyl (-OH) functional group.

• Examples of alcohol – methanol;

ethanol (2-carbon alcohol that can be produced by
yeasts = fermentation)

• Due to the presence of the –OH group, alcohols can exhibit

HYDROGEN BONDING and have relatively stronger
Intermolecular forces of attraction (IMFA) than hydrocarbons
of relatively same size.

• Short carbon chains; relatively polar; can dissolve in water

due to the H-bond.
 Naming ALCOHOLS
• Replace the suffix –ane/-ene/-yne with –anol.
• If there are more than one hydroxyl group (-OH), the suffix is
expanded to include a prefix that indicates the number of –
OH groups present (-anediol, -anetriol, etc)
• The position of the hydroxyl group(s) on the parent chain
is(are) indicated by placing the number(s) corresponding to
the location(s) on the parent chain directly in fromt of the
base name (same as alkenes)
 Naming ETHERS
• The two alkyl groups attached to the oxygen are put in
alphabetical order with spaces in between names
• This will be followed by the word ETHER.
• The prefix di- is used for both alkyl groups are the same.
 Naming ALDEHYDES
• Named by replacing the suffix –ane with –anal.
• If more than one –CHO group, a prefix that indicates the
number of –CHO groups present (-anedial, etc)
• there should not be more than 2 of these groups on the parent
chain as they must occur at the ends
 Naming Ketones
• Named by replacing the suffix –ane with –anone.
• If more than one carbonyl group (C=O), the suffix is expanded to
include a prefix that indicates the number of carbonyl group(s) present
(-anedione, -anetrione, etc)
• The position of the carbonyl group(s) on the parent chain is (are)
indicated by placing the number(s) corresponding to the location(s) on
the parent chain directly in front of the base name (same as alkenes)
 Naming Carboxylic Acids

• Named by replacing the suffix –ane with –anoic acid.

• If there are two -COOH groups, the suffix is expanded to
include a prefix that indicates the number of -COOH groups
present (-anedioic acid - there should not be more than 2 of
these groups on the parent chain as they must occur at the
ends).
• It is not necessary to indicate the position of the -COOH
group because this group will be at the end of the parent chain
and its carbon is automatically assigned as C-1.
Naming Carboxylic Acids
 Naming Esters
• Systematic names of esters are based on the name of the
corresponding carboxylic acid. Remember esters look like
this:

• The alkyl group is named like a substituent using the -

yl ending. This is followed by a space.
• The acyl portion of the name (what is left over) is named by
replacing the -ic acid suffix of the corresponding carboxylic
acid with -ate.
Naming Carboxylic Acids
 Naming Amines
• They are named like ethers, the alkyl (R) groups attached to
the nitrogen are put in alphabetical order with no spaces
between the names and these are followed by the word amine.
• The prefixes di- and tri- are used if two or three of the alkyl
groups are the same. 
• NOTE: Some books put spaces between the parts of the name,
but we will not. Follow the examples.
 HALOCARBONS are organic compound containing
halogens as functional groups.

■ Organic compounds containing halogen atoms covalently

bonded to aliphatic hydrocarbons are called ALKYL
HALIDE.
■ If the halogen atom is bonded to benzene or other aromatic
compounds they are called an ARYL HALIDE. (Ex.
Chlorobenzene)
 HALOCARBONS are organic compound containing
halogens as functional groups.

NAMING HALOCARBONS
1) Aliphatic – a prefix indicates which halogen is present;
change -ine to –o. (fluorine – fluoro)
2) If more than one kind is present in the same molecule, the
halogens are named alphabetically.
3) Number the carbon atoms in such a way that the lowest
position is given to the substituent (branch) that comes first
in the alphabet.
H Br F Cl H
H C C- C C C H 1-bromo-3-chloro-
H H H H H 2-flouro butane
 HALOCARBONS are organic compound containing
halogens as functional groups.

NAMING HALOCARBONS
4) For ARYL HALIDE, the benzene ring is numbered to give
each substituent the lowest position number possible.
 Naming Alkyl Halides
• The halogen is treated as a substituent on an alkane chain. The
halo- substituent is considered of equal rank with an alkyl
substituent in the numbering of the parent chain.

F fluoro-
Cl chloro-
Br bromo-
I iodo-
Functional group Prefix Suffix
carboxylic acids none -oic acid
aldehydes none -al
ketones none -one
alchols hydroxy- -ol
amines amino- -amine
ethers alkoxy- -ether
fluorine fluoro- none
chlorine chloro- none
bromine bromo- none
iodine iodo- none