Organic Chemistry

Organic Chemistry- The study

of carbon & carbon compounds

• Organic compounds are the

primary constituents of all living
organisms.
Draw an electron dot diagram of
carbon.
Χ●
●
Χ C
Χ●
●
Χ

Carbon is able to form 4 covalent

bonds (4 valence electrons) with
other carbon or other elements.
 II. Characteristics of Organic
Compounds
• They are nonpolar compounds – they do
not dissolve in polar solvents like Water.
O-

H+ +H

*remember the rule –

“likes dissolve likes”
4) They have low melting points – due to
weak intermolecular forces.
C-C ● ● ● C-C
STRONG STRONG
weak

5) They react slower than ionic

compounds – due to strong covalent
bonds between atoms.
Structural Formulas –
A 2D model shows bonding patterns and
shapes of molecules

Carbon is found in the center H

H C H
The short line – represents a
H
pair of electrons.
 Draw the structures for each
organic
H
1. Methane: CH4
H C H

2. Chloroform: CHCl3 H H

Cl C Cl

3. Ethane: C2 H6 Cl H H

Remember : Carbon H C C H
has 4 bonding sites. H H
 Types Of Bonds
Single Bond – single covalent bond in
which they share 1 pair of electrons. (2 e-)

● ●
C C ● C C
●● ●
● ●
Double Bond – carbon atoms may
share 2 pairs of electrons to form a
double bond.
● ●
●●
C C ●
C ●● C
●
Triple Bond – carbon atoms may share
3 pairs of electrons to form a triple bond.

C C ●●
●C ●● C ●
●●
 Types Of Compounds
Saturated Compound – organic
compounds in which carbon atoms are
bonded by SINGLE bonds.
ex. Methane: CH4
H
H C H
H
 Types Of Compounds
Unsaturated Compound – compounds
where carbon atoms have double or
triple bonds.

ex. ethene: C2H4

H H
H C C H
 Homologous Series of Hydrocarbons

• Organic compounds can be classified

into groups with related structures and
properties.

***As size of molecule increases the

boiling and freezing points increase.
Hydrocarbons are organic compounds
that consist of only Carbon and
Hydrogen atoms.

H H H
H C H H C C H

H H H
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 single
●Saturated hydrocarbons
 Alkanes = CnH2n+2
• A saturated hydrocarbon contains 5
carbons. What is the formula?
C5H2(5)+2 = C5H12
• A saturated hydrocarbon contains 20
carbons. What is the formula?
C20H2(20)+2 = C20H42

Saturated = Single
Alkanes

• CH4 = methane
• C2H6 = ethane
• C3H8 = propane
• C4H10 = butane
• C5H12 = pentane
The smaller the compound the Lower Boiling
point and Melting point is (less bonds to break)

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 Naming Organic Compounds
• Organic compounds are named according
to the IUPAC (international union of pure &
applied chemistry) system of
nomenclature.
Alkanes – end in ane
Alkenes – end in ene
Alkynes – end in yne
 Alkenes – CnH2n
series of unsaturated hydrocarbons
having one double bond (C=C)
• Also called ethylene
series (IUPAC name is
ethene)
• General formula CnH2n
Alkenes

• C2H4 = Ethene
• C3H6 = Propene
• C4H8 = Butene
• C5H10 = Pentene
• To find the number of
hydrogens, double the
number of carbons.
 1-Butene
This is 1-butene, because the double
bond is between the 1st and 2nd carbon
from the end.

ISOMERS: Molecules have the same

molecular formula, but have different
structural formulas.
Pentene

This is 1-pentene. The double bond is

on the first carbon from the end.

This is not another isomer of pentene.

This is also 2-pentene, just that the
double bond is closer to the right end.
 Alkynes –
a series of unsaturated
hydrocarbons that contain 1 triple
bond.
• Also called the acetylene series

General formula CnH2n-2

C C
Alkynes

• C2H2 = Ethyne
• C3H4 = Propyne
• C4H6 = Butyne
• C5H8 = Pentyne
Alkyl Groups – have one less
hydrogen than the corresponding
alkane.
• CH3 is methyl – one less H than
methane, CH4
H
H C H

H
Draw methyl
C2H5 is ethyl – one less H than ethane C2H6

Condensed
Formula:
CH2CH3

Ethane
C3H7 is propyl – one less H than propane C3H8

propane
 Benzene – a series of cyclic
unsaturated hydrocarbons.
General formula CnH2n-6
Benzene – C6H6 the simplest in the family
H

C
H
C C H

H C C H
C
H
 IUPAC Naming
Branched
Hydrocarbon Chains
Sometimes the hydrocarbon chains
are not straight and sometimes
they have other elements attached
to them. Here is how they are
named:

CH3 - CH2 - CH2 – CH – CH – CH - CH3

CH2 CH3 CH3
CH3
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
Step 1: Find the longest continuous chain
of carbons.
All bonds in the chain of carbons
are single bonds so ending is…ane.
There are 7 continuous carbons, so the
parent chain is heptane.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
4 5 6 7
1 2 3
CH2 CH3 CH3
CH3
• Step 2: Number the carbons in the main
sequence starting with the end that will
give the attached groups the smallest #.
This chain is numbered from right to left
because there is a substituent closest to
the right.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• Step 3 : Add numbers to the names of the
groups to identify their positions on the chain.
- these numbers become prefixes to the parent
chain. yl
ethane
In this ex. the positions are:
C2H6
5
2 - methyl, 3 - methyl, 4- ethyl
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• Step 4: Use prefixes to indicate the
appearance of a group more than once in the
structure.
Di = twice
Tri = three times
Tetra = four times
Penta = five times
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• This chain has 2 methyl groups so
dimethyl
is used.

Step 5: List the alkyl groups in alphabetical

order.
In this ex. dimethyl is listed before the ethyl.
7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3

Step 6: Use punctuation

- use commas to separate numbers
-hyphens to separate numbers with
words.
 7 6 5 4 3 2 1
CH3 - CH2 - CH2 – CH – CH – CH - CH3
CH2 CH3 CH3
CH3
• The name of this compound is:

2,3-dimethyl – 4-ethyl heptane

 CH3 CH3
CH3 - CH2 – CH – CH2 – CH - CH3
6 5 4 3 2 1

Step 1: 6 carbons = hex

All single bonds = ends in ane
So parent chain is hexane

Step 2: start numbering from right to left

Step 3: 2 -methyl and 4 -methyl
 CH3 CH3
CH3 - CH2 – CH – CH2 – CH - CH3
6 5 4 3 2 1

2,4 dimethyl hexane

When naming with a double/triple bond-
start # carbons closest to the bond.

CH3 CH3

C C C C C
1 2 3 4 5

3,4 dimethyl, 2-pentene

Now start with name and draw the structure.
• 3-ethylhexane
C C C C C C
CH2
CH3
You can place H’s all around or just leave as is.

H C H
yl
H C H ethane
C 2H 6
H 5
• 2,2,4-trimethylpentane

CH3
C C C C C

CH3 CH3
 Other Organic Compounds
Functional Groups – specific groupings of atoms
that give characteristic properties to organic
compounds.

halides F (fluoro-)
Cl (chloro-)
Br (bromo-)
I (iodo-)
What group do these belong to?
Halogens
• Alcohols -OH hydroxyl

• Organic acids -COOH carboxyl

• Aldehydes O -CHO carbonyl

• Ketones -C-
• Ethers -O-
O
• Esters -C-O
• Amines -N- O
• Amides -C-NH
 Halides
Cmpds that are formed
when any halogen
(F,Cl,Br,I) replaces an
H atom in an alkane.

The functional
group is the halide
(F,Cl,Br,I)
 Halides
• They are named by citing the location of the
halogen attached to the chain
Drop the “ine” and add “o”
F

2- fluoropropane
 Alcohols
• Are organic cmpds in which one or more of the
hydrogens is replaced with an – OH group.

- OH group is called the hydroxyl group

Monohydroxyl Alcohols
-have one –OH group
H
R C OH

H
Shortcut way to represent a primary alcohol
R-OH
R stands for REST of the molecule
 IUPAC naming of alcohols
• Replace the final “e” with “-ol”
● methane methanol CH3OH
● ethane ethanol C2H5OH
● propane propanol C3H7OH
● butane butanol C4H9OH
● pentane pentanol C5H11OH
Ex. 2-propanol

H OH H
H C C C H
H H H

1 2 3
 Organic acids – have the
functional group -COOH
• R-COOH
O
Carboxyl
R C
group OH
 IUPAC naming of Organic Acids
 Replace the final “e” with “-oic ”acid
H
Methanoic acid - HCOOH
O H C H
R C H
OH
Aldehydes- contain the functional
group -CHO
R-CHO O
R C
H
 IUPAC naming of Aldehydes-
• Replace the final “e” the the ending “al”
First member of the aldehyde family is methanal
-its common name is formaldehyde
Used to
2 O preserve
H C 3 biological
1 samples
4 H
• Alcohols can be oxidized to aldehydes

H O
R C OH + Oxidizing R C + H20
agent H
H
methanol methanal water
Draw ethanal

H
O
H C C
H
H
 Ketones – contain the functional
group R-CO-R
 Replace the final “e” with “-one”.

• The simplest member

of the ketone family is
propanone.
• IUPAC name is propanone but its
common name is acetone, it is an
important industrial solvent.
R R

H O H

H C C C H
H H
Ethers -
• when two primary alcohols are treated
with a dehydrating agent, water is
removed and the 2 alcohols are joined
together by an oxygen “bridge”.
R-OH + R-OH R-O-R + H20

Primary Primary ether

alcohol alcohol

H2O
 Diethyl ether- used as a general
anesthetic
ethyl ethyl

H H H H

H C C O C C H
H H Oxygen bridge H H

Condensed formula
CH3 CH2 -O- CH2 CH3
 Dimethyl ether-
methyl methyl

H H

H C O C H
H Oxygen bridge H

Condensed formula
CH3 -O- CH3
Name These:
Condensed
formula CH3-O- CH2 CH3
Methyl ethyl ether

CH3CH2-O- CH2CH2CH3
Ethyl propyl ether
 Esters – are organic cmpds with the
general formula R-CO-O-R
O
They are formed in a rxn
between an organic acid C O
and an alcohol.
Draw this:

Esters have strong fragrant aromas and are

what make pineapples, bananas,
wintergreen & oranges so YummY!
 IUPAC naming of Esters:
H H O H H
H C C C O C C H
H H H H

O
1. Look at chain after the –C-O- write its prefix
Ex.(meth,eth, etc.) and add –yl to the end of
prefix
In this ex. : eth + yl = ethyl
 H H O H H
H C C C O C C H
H H H H
Condensed formula
CH3 CH2 COO CH2CH3
2. Give the name of the carbon chain that
includes the C=O, leave off the last letter
and add –oate. Propane - 3 C’s and single bonds
propane + oate = propanoate
Ethyl propanoate
 Ex.) Draw ethyl pentanoate

H H H H O H H
H C C C C C O C C H
H H H H H H

Now you’ve got it!

 Amines – contain the functional
group -N-
• It is a derivative of ammonia – NH3
• IUPAC naming of amines –
- replace the final –e with “-amine”

H Draw:

H C NH2 C C NH2

H
ethanamine
methanamine
 Amides – contain the functional
group: O
C NH
Found at the end of a carbon chain
• IUPAC naming of amides:
-drop the final –e and add “amide”
H H O
H C C C NH2 propanamide
H H
Amide

butanamide

Synthetic Polyamides: nylon, kevlar

Natural Polyamide: silk!
 Organic Reactions
• Substitution – replacement of one kind of
atom or group with another atom or group
• If this rxn occurs between an alkane
and a halogen, it is called
halogenation.

*only happens with alkanes –

single bonds!!!!
 Substitution

+ Br2 Br + HBr

Hydrogen
Butane + bromine Bromobutane +
bromide

C4H10 + Br2  C4H9Br + HBr

The second Br can then substitute for another H.

For Ex: Find the products of

C3H8 + F2  C3H7F + HF
 Addition –adding one or more
groups at a double or triple bond.
• Double bond is broken…becomes a
single bond.

*only happens with alkenes &

alkynes – double/triple bonds!!!!
 Addition
• Alkene + Halogen  Alkyl Halide
• The double bond is broken, and the
halogen adds at either side of where the
double bond was.
saturated

unsaturated
 Fermentation
-Molecules are broken down
- enzymes act as catalysts
-Anaerobic respiration

glucose ethanol + Carbon

dioxide
 Esterification
• Organic Acid + Alcohol  Ester + Water
-COOH -OH -COO -H2O

-These are slow reversible reactions

-similar to neutralization rxn in inorganic

Acid + base = salt + water

Saponification – is the hydrolysis of
fats by bases.
• The breaking of an ester to produce an
organic acid plus an alcohol.
(glycerol ester) (soap) (alcohol)
Fat + water = organic acid + glycerol

What is this the reverse process of?

Esterification
Organic Acid + Alcohol  Ester + Water
Saponification - hydrolysis of an ester
in presence of a hot base (alkali)
Glycerol ester + 3 NaOH  soap + glycerol

Fat base alcohol soap

 Polymers- are composed of many
repeating units of monomers
• Natural polymers
-starch – long chains of sugars
-proteins – long chains of amino acids
-cellulose – made of repeating units of sugar

starch cellulose
 Polymers
• Synthetic (man made) polymers:
- nylon, rayon - polyester

- polyethylene - silicone
 Polymerization- formation of
polymers from monomers
• Formation of larger molecules from smaller
ones. :
2 Methods

1. Condensation polymerization: bonding

of monomers by dehydration synthesis
 Monomers have at least two functional groups
 -OH on ends
 Condensation polymerization
Ex.) H 2O
H H H H
HO C C
HO
+ HO C C
HO
H H Leaves an H H
monomer oxygen bridge monomer

H H H H
+
O HO
HO C C C C H 2O
H H H H
polymer
 Addition Polymerization -
C C + C C + C C
monomer
monomer monomer
ethylene
ethylene
ethylene
C C C C C C

polymer

polyethylene
 Finding missing reactants &
products in organic rxns
• In balanced rxns the number of atoms on the
left must equal the number of atoms on the
right. Ex.) C2H6 + Cl2 C2H5Cl +
Left side Right side missing
C= 2 C= 2 C= 0
H= 6 H= 5 H= 1
Cl = 2 Cl = 1 Cl = 1
Missing product must be HCl
This is a substitution rxn because hydrogen
atom of ethane is replaced by chlorine.
• Try this one: Ex.) C2H4 + Br2 C2H4 Br2
This is a addition rxn

 What process makes…

saponification
combustion
fermentation

addition
polymerization
Condensation
polymerization