Organic Chemistry

K A R L C H R I S TO P H E R L . W E B E R , R M T, M S M T © , M L S ( A S C P I ) C M , N Y ( C LT )
D E PA RT M E N T O F M E D I C A L T E C H N O LO G Y/ M E D I C A L L A B O R ATO RY S C I E N C E
C O L L EG E O F A L L I E D M E D I C A L H E A LT H S C I E N C ES
U N I V E R S I T Y O F N E G R O S O C C I D E N TA L R E C O L E TO S
Learning Objectives
At the end of the topic, the students should be able to:
1. Define organic chemistry
2. Identify hydrocarbon compounds
3. State the properties and uses of hydrocarbon
4. Name some hydrocarbons using IUPAC and common names
5. Give the structures of the functional groups

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Organic chemistry
is a branch of chemistry that deals with the study of
carbon and its compound.

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Definition of Terms:

 hydrocarbons – usually they contain hydrogen atoms and perhaps other

atoms, such as oxygen, nitrogen, sulfur, and halogens

 aromatic hydrocarbons – contain benzene rings; six-membered rings of carbon

atoms with alternating single and double carbon-carbon bonds or similar
structural features

 aliphatic hydrocarbons – contain no benzene rings, usually straight chain and

sometimes closed chain
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Definition of Terms:
 saturated hydrocarbons – carbon to carbon single bond, usually
soluble in water

 unsaturated hydrocarbons – contains double(=) or triple(≡) carbon

to carbon bond, usually insoluble in water

 alkane – also called as paraffins; a hydrocarbon in which all carbon

atoms are bonded to the maximum number of hydrogen atoms
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 Definition of Terms:
 cycloalkanes – are saturated hydrocarbons in which the carbon atoms form a ring

 alkene – it contains a carbon-carbon double bond; also called olefins

 alkynes – are unsaturated hydrocarbons containing a carbon-carbon triple bond

 benzene - six-membered rings of carbon atoms with alternating single and double
carbon-carbon bonds
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 General formulas and structures
alkane – CnH2n+2
if n=1 therefore: CH4
if n=2 therefore: C2H6

alkene – CnH2n
if n=3 therefore: C3H6
if n=4 therefore: C4H8

alkyne – CnH2n-2
if n=5 therefore: C5H8
if n=6 therefore: C6H10
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General formulas and structures
o cycoalkane – CnH2n

cyclobutane cyclopropane cyclohexane

benzene – C6H6

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ALKANES
OCCURRENCE
◦ The most important source of alkanes is natural gas and fossil oil.
◦ Natural gas contains primarily methane and ethane alongside
some propane and butane.
◦ Methane is also present in biogas produced by methanogenic
bacteria acting on decaying animal and vegetable matter.
◦ Fossil oil is a mixture of liquid alkanes and other hydrocarbons

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Properties of alkanes
Alkanes are Nonpolar
Boiling points, melting points, and densities generally increases with the size of
the alkane:
◦ Decane > Heptane > Butane
◦ Straight chain alkanes have a higher boiling point than branched alkanes due to the greater
surface area in contact.

Alkanes containing 1 to 4 carbons are gases at room temperature

Alkanes containing 5 to 17 carbons are colorless liquids
Alkanes containing 18 or more carbons are white, waxy solids.
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ALKANES
Uses of Alkanes
◦ Pentane to octane reasonably volatile liquids that are used as fuels in internal
combustion engines. They are also good solvents for nonpolar substances.
◦ Nonane to hexadecane are used as kerosene and jet fuel.
◦ Alkanes from hexadecane are liquids of high viscosity and are commonly used
as lubricating oil.
◦ Petroleum jelly, a semi-solid mixture of hydrocarbons (mainly higher than 25
carbons), is used as a skin protectant in cosmetic skin care
◦ Many solid alkanes find use as paraffin wax in candles.

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Types of Alkanes
1. Linear alkanes have the carbons bonded together in a chain-like
structure, similar to a snake
2. Branched alkanes are derived from linear alkanes, but instead of
having just a straight chain in their chemical structure, it is branched
with one or more alkyl groups.
◦ alkyl group is a group of carbon and hydrogen atoms attached to an alkane
molecule
3. Cyclic alkanes or cycloalkanes consist of hydrogen and carbon atoms
bonded together with single bonds, where the carbon atoms bond
together to form a ring or loop. 14
ALKENES
Physical Properties of Alkenes
◦ Alkenes are non-polar, and they are both immiscible in
water and less dense than water.
◦They are generally soluble in organic solvents.
◦ they do not conduct electricity.

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ALKENES
Reactivity of Alkenes
◦ Alkenes are more reactive than their related alkanes due
to the relative instability of the double bond.
◦ They are more likely to participate in a variety of
reactions, including combustion, addition, hydrogenation,
and halogenation reactions

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ALKENES
Uses of Alkenes --Plastics and Rubber
◦ simple alkenes, for instance ethene and propene, are essential for the
manufacture of polymers like polystyrene and polyvinyl chloride (PVC) that
are needed to make plastic products
◦ alkene, 1,3-butadiene, is also responsible for the manufacture of plastic
products like our toilet seats, which is something that we use every day.
Besides plastic products
◦ 1,3-butadiene is also used to manufacture rubber products like golf club
heads and bumper bars.

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 PROPERTIES OF ALKYNES
The physical properties of alkynes are very similar to those of the alkenes.
◦ The first three members of alkyne family — ethyne, propyne and butyne are
colourless gases, the next eight members are liquids and the higher ones are solids.
Except for ethyne, which has characteristic smell, all members are odourless.
◦ The boiling point of alkynes increases with molar mass. Among hydrocarbons,
alkynes have higher boiling point than alkenes and alkanes because of the presence
of triple bond in alkynes.
◦ Alkynes like alkanes and alkenes are non-polar; therefore, they are insoluble in water
but readily dissolve in organic solvents such as ether, carbon tetrachloride and
benzene.
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Some Interesting Alkynes
◦ Acetylene (H-CC-H) is a colorless gas that burns in oxygen to form
CO2 and H2O. The combustion of acetylene releases more
energy per mole of product formed than any other hydrocarbons.
It burns with a very hot flame and is an excellent fuel.

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NOMENCLATURE/NAMING
Alkane, Alkene and Alkyne

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branches or substituents attached to the carbon
atom in the hydrocarbon chain.
Halogen Group
Br – bromo
Cl – chloro
F – fluoro
I – iodo
Halogen branch

4-bromo-2-chloro-1-fluoro-3-iodoheptane
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Alkyl Group – use the name with –yl ending if it becomes a branch
methane – methyl CH3 -
Ethane – ethyl CH3-CH2 -
propane – propyl CH3-CH2-CH2 -
Butane – butyl CH3-CH2-CH2-CH2 -
pentane – pentyl CH3-CH2-CH2-CH2-CH2 -

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Alkyl branch
◦ 3-methylheptane

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 Rules in naming Alkanes

 Locate the longest continuous chain in the series of carbon

atoms. Assign a number to the carbon atom starting from the
end closest to the branch.
 Alphabetized the alkyl and halogen branches and assign a
number to where it is attached.
 Use the Greek prefixes (di-,tri-,tetra-,penta-) for more than
one same branches.

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EXAMPLES

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Cycloalkanes

cyclopropane cyclobutane

cyclohexane 27
Rules in naming Cycloalkane
 Substituents are named similarly to straight-chained
alkanes. The carbons in the ring are numbered so that the
substituents have the smallest numbers.
Add the prefix cyclo- to the alkane name

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EXAMPLES

1-bromo-2-chlorocyclopropane

1,2-ibromo-3-fluorocyclobutane

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ALKENES, ALKYNES, AROMATIC
HYDROCARBONS

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alkenes
unsaturated hydrocarbons that contain one or more carbon-carbon
double bonds.
the simplest alkene is ethene or ethylene

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ALKYNES
unsaturated hydrocarbons that contain one or more carbon-carbon triple bonds
the simplest alkyne is ethyne or acetylene
◦

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Ethylene AND ETHEPHON
ethylene (ethene)
◦ natural ripening agent for fruits

ethephon
◦

Upon metabolism by the plant, it is converted into ethylene

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cis-trans isomers
cis-trans isomers
◦ isomers that have the same connectivity of their atoms but a
different arrangement of their atoms in space.

◦ cis-trans stereoisomers result from the presence of either a ring of

a carbon-carbon double bond

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 cis-trans isomers
 Cis–trans isomerism, also known as geometric isomerism or
configurational isomerism

 cis indicates that the functional groups are on the same side of
the carbon chain while trans conveys that functional groups are
on opposing sides of the carbon chain.

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cis-trans isomers
2-butene
cis-2-butene and trans-2-butene
◦

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Naming an alkene (IUPAC)
RULES:
1. Find the longest chain containing the double bond and assign a number to
the carbon atom nearest to the double bond.
2. Indicate the number of the carbon atom where the double bond is located.

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3. For branching alkene, the branch chains are named as in alkanes.

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Examples (alkenes)

3,6-decadiene

7,8,8-tribromo-6-ethyl-6,7-dimethyl-2,4-nonadiene

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Naming alkyne (IUPAC)
The alkynes are named by IUPAC rules in the same way as the alkenes:
suffix is -yne instead of –ene

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Combined double bond and triple bond

A molecule that contains both double and triple bonds is called an

alkenyne. The chain can be numbered starting with the end closest to
the functional group that appears first.

6-ethyl-3-methyl-1,4-nonenyne
or 6-ethyl-3-methyl-4-nonen-1-yne

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Cycloalkene and cycloalkyne
Basic rules of naming cycloalkenes
1. Number the carbon atoms in the ring so that double bond is
between carbon atom1 and carbon atom2.
2. Give lower numbers to the group/branch encountered first.
3. Number and list groups in alphabetical order.

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1.

2.

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3.

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4.

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answers

1.

2.

3. 2,3,4,6-tetrachloro-1,8-decenyne
2,3,4,6-tetrachloro-1-decen-8-yne

4. 1,5-dimethylcyclopentene

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Aromatic hydrocarbon
benzene and its
derivatives

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Aromatic Hydrocarbon
 aromatic hydrocarbon is also known as arene

removal of H from alkane is called alkyl group (R-)

 removal of H from an arene is called an aryl group (Ar-)

 removal of H from benzene, - called phenyl group

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Kekule structure

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Fused-ring aromatic hc

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Rules in naming Benzene
1. The parent structure is the fused-ring benzene. Assign the
smallest possible numbers to indicate the location of the branched
alkanes. Start numbering where the substituent is located and if
there is only one branch no need to put a number.
2. Identify the different branch groups attached to the benzene ring.
3. Follow this format: (location of branch)-(branch name)(parent
chain)

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Derivative of phenol

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Naming:
When two groups are on the benzene ring, three
isomers are possible. Use the prefixes ortho- (o),
meta- (m), and para- (p)

1,2- or ortho-
1,3- or meta-
1,4- or para-
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A numbering system is used, to show the positions of two or more groups:

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