An organic compound is one that has carbon

as the principal element

•Carbon is unique

•It has 6 electrons in its outer shell

arranges 1s22s2sp2 e e e
e
•It has room for 4 bonds to 4 other
atoms.

e
e

Organic compounds have specific geometry

around the carbon to carbon bond
The carbon atom forms bonds in a
tetrahedral structure with a bond
angle of 109.5O.

So a chain of carbon atoms makes

a zigzag pattern
•Introduction
•A hydrocarbon is a compound
consisting of only hydrogen and
carbon.
•The carbon to carbon can be single,
double, or triple bonds.
•The bonds are always nonpolar
Carbon-to-carbon bonds can be:

Single

Triple.
Double

Note that in each example, each carbon

atom has four dashes, which represent four
bonding pairs of electrons, satisfying the
octet rule.
Carbon-to-carbon chains can be

(A) straight

(B) branched

(C) closed ring.

 Naming alkanes

•Identify the longest continuous chain.

•The locations or other groups of atoms attached to
the longest chain are identified and numbered by
counting from the end of the molecule which keeps
the numbering system as low as possible.
•Hydrocarbon groups that are attached to the
longest continuous chain and named using the
parent name and changing the –ane suffix to –yl
Step-1 Identify the longest continuous chain

• Where is the longest continuous chain of carbons?

Prefixes for root word of Carbons

n 1 Meth 6 Hex

2 Eth 7 Hept

3 Prop 8 Oct

4 But 9 Non

5 Pent 10 Dec
 Endings

• Alkanes (all C-C single bonded parent

chain) end in –ane
– Methane CH4
– Ethane C2H6
– Propane C3H8
• Attached carbon groups (substituents) end
in –yl
– Methyl CH3 -
– Ethyl CH3CH2-
– Propyl CH3CH2CH2 –
3-ethylpentane
Step 2. Number the parent chain.

• Number the parent chain so that the attached

groups are on the lowest numbers
Methyl is on carbon #2 of the parent chain
Methyl is on carbon #4 of the parent chain

1 2 3 4 5 red is the right way for

5 4 3 2 1 this one!

18 27 Groups on 4, 6, and 7
36 72 81 1 2 3 4 5 6
45 54 63 1 6 5 4 3 72
1
Groups on 2, 3, and 5 Groups on 2 and 5 Groups on 3 and 6
Step 3. Name the attached groups.

• Carbon (alkyl) groups

– Methyl CH3 -
– Ethyl CH3CH2-
– Propyl CH3CH2CH2 –
• Halogens
– Fluoro (F-)
– Chloro (Cl-)
– Bromo (Br-)
– Iodo (I-)
Step 4. Designate where the group
is attached to the parent chain.
• Use the numbers of the parent chain from
step 2 to designate the location of the
attached groups to the parent chain.
2-methyl

1 2 3 4 5
Step 5. Alphabetize the groups,
combine like groups, and assemble.
• The prefixes di, tri, tetra
etc., used to designate
several groups of the same
kind
• Prefixes are not considered
when alphabetizing
(Example: dimethyl = m for 1,1,1-trichloro-1- 1,1-dichloro-1,1-
fluoromethane difluoromethane
alphabetizing)
• Parent chain goes LAST
 Structural Formulas
• “Lazy” way to write the Hydrogens
• Instead of drawing the bonds, just state
how many hydrogens are attached
• NOTE: The bonds are between
CARBONS in a parent chain, and not
hydrogens!

Structural Formula

Lewis Structure
 Order of Priority
• IN A TIE, halogens get the lower number
before alkyl groups

5 4 3 2 1

4-chloro-2-methylpentane or
2-chloro-4-methylpentane?
 Order of Priority
• IN A TIE between SIMILAR GROUPS, the
group lower ALPHABETICALLY gets the
lower number

4-bromo-2-chloropentane or
2-bromo-4-chloropentane ?
 Isomers
Isomers: Compounds with same molecular formula but
different structures.

• Straight chain alkanes: An

alkane that has all its carbons
connected in a row.

•Branched chain alkanes: An

alkane that has a branching
connection of carbons.
• Petroleum
products
and the
ranges of
hydrocar-
bons in
each
product.
• There is only one possible way
that the carbons in methane (CH4),
ethane (C2H6), and propane (C3H8)
can be arranged.
 • However, carbons in butane (C4H10) can
be arranged in two ways; four carbons in a
row (linear alkane) or a branching
(branched alkane). These two structures
are two isomers for butane.
 •Different isomers are completely different
compounds. They have different structures,
different physical properties such as melting
point and boiling point, and may have different
physiological properties.
• Number of possible isomers increases
rapidly with the number of carbons
– C30H62 – >4 billion possible isomers
 Properties of Alkanes
• Main property: will burn
 C C C
Types of Carbon AtomsH
• Primary carbon (1o) H
– a carbon bonded to
one other carbon
C C H
H
• Secondary carbon (2o)
H
– a carbon bonded to H
two other carbons C C C
C C C H
H
• Tertiary carbon (3o) H H
C C
– a carbon bonded to H C C C
three other carbons H C
C C H
C C H C
Unsaturated Hydrocarbons
• Can have more hydrogen atoms added
• Very important in biological systems
• Alkene: hydrocarbon that contains one
or more carbon-to-carbon double
bonds
• To show the presence of the double
bond, the –ane suffix from the alkane
name is changed to –ene.

– General formula of CnHn

• Simplest: ethylene, C2H4
• Ethylene is the gas that ripens fruit, and a ripe fruit
emits the gas, which will act on unripe fruit. Thus,
a ripe tomato placed in a sealed bag with green
tomatoes will help ripen them.
Naming of Alkene is similar to naming alkanes
except:
• The longest continuous chain must contain
the double bond.
• The base name now ends in –ene.
• The carbons are numbered so as to keep the
number for the double bond as low as
possible.
• The base name is given a number which
identifies the location of the double bond.
 Alkynes

• Alkyne: hydrocarbon that

contains one or more carbon-to-
carbon triple bonds
• Naming an alkyne is similar to
the alkenes, except the base
name ends in –yne.

• General formula of CnH2n–2

• Simplest: acetylene, C2H2
 Properties of Alkenes and Alkynes
• Similar physical properties to alkanes

• Undergo more reactions than alkanes

– Addition reaction: add compounds across double

bond
– Importantly, they can form polymers
 Cyclic Hydrocarbons
• Carbon atom chains in form of rings
• Can be represented by structural
formulas or symbolic representations
• Cycloalkanes and Aromatic Hydrocarbons
– Cycloalkanes are alkanes (only carbon to carbon
single bonds) which form a ring structure.

• The "straight" chain has carbon

atoms that are able to rotate freely
around their single bonds,
sometimes linking up in a closed
ring.
• (B) Ring compounds of the first
four cycloalkanes.
– An aromatic compound is one that is based on the
benzene ring(C6H6).
H
– Structure: Alternating single & Double Bonding
H H

H H

–A benzene ring that is attached to another compound is

given the name phenyl.
 Functional Groups
• Group of atoms that gives a family
of organic compounds its
characteristic chemical and
physical properties
• Alkyl group: derived from alkane by
removing a H
– R stands for alkyl group in general
 Halogens

– Halogens (F2, Cl2, Br2, I2,) can all add to a

hydrocarbon to form am alkyl halide.
• When naming the halogen the –ine ending is
replaced by –o
• Fluorine becomes fluoro
• Chlorine becomes chloro
• Bromine becomes bromo
• Iodine becomes iodo
Common examples of organic halides.
 Alcohol Family
• –hydroxyl(OH) group
• Replace -e with -ol
• CH3OH, methanol, simplest
• Produced industrially
– Mainly a chemical intermediate
• C2H5OH, ethanol
• Made industrially and by fermentation
– Industrially produced alcohol has noxious
substances added
• Small, simple alcohols tend to be toxic
 Multifunctional Alcohols
• Several common alcohols have more than one –OH
group
• Ethylene glycol: main ingredient in antifreeze
• Glycerol: used in lotions
– Ingredent in some explosives
 Ethers
• Two alkyl groups attached to same O
– Example CH3CH2-O-CH2CH3
• Used mainly as solvent
• Little chemical reactivity
– Insoluble in water
– Highly flammable
 Aldehydes and Ketones
• Both contain carbonyl group (C=O)
• Aldehyde: R-CHO
• Ketone: R-CO-R’
 Common Aldehydes
• Change -e ending to -al
• Produced by oxidation of alcohols
• Formaldehyde – used as a preservative
• Larger ones used as fragrances
– Benzaldehyde – flavor in maraschino
cherries O

C H
 Common Ketones
• Change -e ending to -one
• Acetone most common ketone
– Used primarily as a solvent
• Produced by oxidation of alcohols

C
H3 C CH3
 Carboxylic Acid
• Contains C=O and –OH group on same
carbon
• Change -e to -oic acid
• Acetic acid: acid in vinegar
O

R C

OH
 The red ants, like other ants, make the
simplest of the organic acids, formic acid.
The sting of bees, ants, and some plants
contains formic acid, along with some other
irritating materials. Formic acid is HCOOH.
 Esters
• Derived from carboxylic acids and
alcohols
• Tend to be fragrant
– Methyl butyrate apple
– Ethyl butyrate pineapple
– Ethyl formate rum
– Methyl salicylate wintergreen