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 H
H C H
Carbon is found in the center
H
The short line – represents a pair of electrons.
Draw the structures for each organic
1. Methane: CH4 H
H C H
H H
2. Chloroform: CHCl3 Cl C Cl
Cl H H
3. Ethane: C2 H6
H C C H
Remember : Carbon has 4 H H
bonding sites.
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 = C H
5 12
• 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
Classification of carbon atoms
Carbons have a special terminology to describe how many
other carbons they are attached to.
● Primary carbons (1o) attached to one other C atom
● Secondary carbons (2o) are attached to two other C’s
● Tertiary carbons (3o) are attached to three other C’s
● Quaternary carbons (4o) are attached to four C's
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
Heterocyclic Aromatic Compounds
at least one carbon
atom is replaced by
one of the
heteroatoms
oxygen, nitrogen,
or sulfur.
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
In this ex. the positions are: ethane
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.
yl
H C H ethane
C2H6
H C H 5
H
• 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
Methanol (methyl alcohol)
produced by heating wood chips in the absence of air.
common name wood alcohol.
a polar organic solvent and is widely used as an industrial solvent.
It is more toxic than ethanol
may cause blindness or death if large amounts are inhaled or ingested.
Ethanol (ethyl alcohol)
Produced since prehistoric times, mostly through the fermentation of fruit juices.
also known as grain alcohol because it is often made from grains, such as corn
(maize), wheat, rye, and barley.
excellent motor fuel with a high octane rating and low emissions; however, it
should be used in a fuel system designed to withstand the alcohol’s tendency to
dissolve plastic parts.
Isopropyl alcohol (2-propanol)
Made by indirect hydration of propylene (CH2CHCH3).
Isopropyl alcohol is commonly used as an industrial solvent and as a
rubbing alcohol applied to the skin.
Is more toxic than ethanol, it has less of a drying effect on the skin,
Glycerol (also called glycerine)
is a sweet syrupy substance with three alcohol hydroxyl groups. Its
systematic name is propane-1,2,3-triol.
Was first obtained as a by-product of soap manufacture, through the
saponification (hydrolysis in base) of fats.
During World War II, large quantities of glycerol were needed for the
production of glyceryl trinitrate (nitroglycerin) (dynamite)
Nitroglycerin is also used as a coronary vasodilator (a drug that relaxes and
expands blood vessels) for symptomatic relief of chest pain caused by poor
circulation to the heart.
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
Methanoic acid - HCOOH
H
O H C H
R C
OH H
Formic acid, the simplest carboxylic acid, is employed in textile
treatment and as an acid reducing agent.
Acetic acid - used in the production of cellulose plastics and
esters.
Aspirin, the ester of salicylic acid, is prepared from acetic acid.
Palmitic acid and stearic acid - manufacture of soaps,
cosmetics, pharmaceuticals, candles, and protective coatings.
Stearic acid - used in rubber manufacture.
Acrylic acid - production of polymers (long-chain molecules)
known as acrylates.
Oleic acid - manufacture of soaps and detergents and of
textiles.
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
Oxidizing
R C OH + agent R C + H 20
H
H
methanol methanal water
Formaldehyde is a gas but is generally handled as a 37 percent solution in water,
called formalin. It is used in tanning, preserving, and embalming and as a
germicide, fungicide, and insecticide for plants and vegetables, but its largest
application is in the production of certain polymeric materials. The plastic Bakelite
is made by a reaction between formaldehyde and phenol.
Aldehydes occur naturally in
flavouring agents.
Benzaldehyde, which
provides the odour and
flavour of fresh almonds
cinnamaldehyde - oil of
cinnamon.
vanillin - the main flavouring
agent of vanilla beans.
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” + H2O
Primary Primary ether
alcohol alcohol
H 2O
Diethyl ether- used as a general anesthetic
ethyl ethyl
H H H H
H C C O C C H
H H H H
Oxygen bridge
Condensed formula
CH3 CH2 -O- CH2 CH3
Dimethyl ether-
methyl methyl
H H
H C O C H
H H
Oxygen bridge
Condensed formula
CH3 -O- CH3
Name These:
Condensed
formula CH3-O- CH2 CH3
Methyl ethyl ether
CH3CH2-O- CH2CH2CH3
Ethyl propyl ether
Ethers are also important in medicine and pharmacology,
especially for use as anesthetics. For example, diethyl ether
(CH3CH2―O―CH2CH3), simply known as ether, was first used as
a surgical anesthetic in 1842. Codeine, a potent pain-relieving
drug, is the methyl ether of morphine. Because ether is highly
flammable, it has largely been replaced by less-flammable
anesthetics, including nitrous oxide (N2O) and halothane
(CF3―CHClBr).
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
methanamine ethanamine
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.)
H2O
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 C C C C H2O
HO
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
1. 2.
Cl
4.
3.
5. 6.
2-butanol
https://www.slideshare.net/wewwchemistry/hybridisation-of-the-carbon-atom?from_action=save
Brown, W. H. (2019, March 28). ketone. Encyclopedia Britannica.
https://www.britannica.com/science/ketone
