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
< TARGET="display">
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)
< TARGET="display">
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
1 2 3 4 5 6 7
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:
C 2H 6
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
C2H6
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 + H2 0
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
Butane bromine Bromobutane + Hydrogen
+ 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 H2O
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
