A review on the
Basic Concepts
of 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.
The structures for each
organic molecule H
1. Methane: CH4
H C H
2. Chloroform: CHCl3 H
H
Cl C Cl
3. Ethane: C2 H6 H H
Remember : Carbon has 4 Cl H C C H
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.
H
ex. Methane: CH4
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
In this ex. the positions are: ethane
2 - methyl, 3 - methyl, 4 - ethyl C 2H6
5
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
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
R C
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 preserve
2 O biological samples
H C 3
1
4 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
H2 O
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
CH3 CH2 -O- CH2 CH2 CH3
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 and an alcohol. C O
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
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
O
group:
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!
