COURSE OUTLINE
Course Code: ORGCHEM 1
Course Title: Organic Chemistry
Course Description:
The fundamental structures of organic molecules and the comprehensive understanding
of the reactions and properties of organic molecules (from kinetic, thermodynamic, and
mechanistic viewpoints) is developed and applied to the synthesis of organic compounds and to
an appreciation of nature’s important molecules.
Course Credit: 5 units ( 3 units lec & 2 units lab)
WEEK TOPICS
1 Importance of Organic Chemistry
Definition of terms
2 Hydrocarbons & Hydrocarbon Derivatives
3 Alkanes
4 Cycloalkanes
5 PRELIMINARY EXAM
6 Alkenes & Cycloalkenes
7 Alkynes
8 Aromatic Hydrocarbons
9 Introduction to Organic Functional Groups & their
Chemistry
10 MIDTERM EXAM
11 Alcohols
12 Aldehydes
13 Ketones
14 Carboxylic Acids
15 Ethers
16 Esters
18 FINAL EXAMINATION
References:
Brown, Le May et.al. Chemistry: The Central Science.
De Guzman, Calanasan et.al. Introduction to College Chemistry
Morrison & Boyd. Organic Chemistry
Sackheim G. and D. Lehman. Chemistry for the Health Sciences
Web: http://infotrac.galegroup.com/itweb/phuphs
http://site.ebrary.com/lib/uphsl
Prepared by: Ernilda L. Decena, PhD
LECTURE 1
Organic chemistry is the study of the structure, properties, composition, reactions, and
preparation of carbon-containing compounds. The most common elements found in organic
compounds are carbon, hydrogen, oxygen, nitrogen, phosphorous, sulfur (C,H,O,N,P,S) and the
halogens, bromine, chlorine and iodine. This branch of chemistry was originally limited to
compounds produced by living organisms but has been broadened to include human-made
substances such as plastics. The range of application of organic compounds is enormous and also
includes, but is not limited to, pharmaceuticals, petrochemicals, food, explosives, paints, and
cosmetics.
Organic chemistry is a highly creative science in which chemists create new molecules and
explore the properties of existing compounds. Organic compounds are all around us. They are
central in the rubber, plastics, fuel, pharmaceutical, cosmetics, detergent, coatings, dyestuff, and
agrichemical industries, to name a few. The very foundations of biochemistry, biotechnology, and
medicine are built on organic compounds and their role in life processes. Many modern, high-tech
materials are at least partially composed of organic compounds . Organic chemists spend much of
their time creating new compounds and developing better ways of synthesizing previously known
compounds.
Properties of Organic Compounds:
1. Formed by covalent linkage
2. Burn readily
3. Less soluble in water, more soluble in organic liquid like alcohol, ether, chloroform
and benzene
4. Less stable toward heat
5. Rarely ionize
6. Less reactive
Organic Chemistry
Hydrocarbons Hydrocarbon Derivatives
Aromatic Aliphatic Alkyl Alcohols Carboxylic Ethers Esters
Halides Acids
Alkanes Alkenes Alkynes Aldehydes Ketones
Cycloalkanes Cycloakenes
HYDROCARBONS
& HYDROCARBON DERIVATIVES
ALKANES(PARAFFINS) CnH2n+2
Hydrocarbons are organic compounds composed solely of carbon and hydrogen atoms.
Atoms are bounded together by covalent bonds.
Alkanes are saturated hydrocarbons. Saturated hydrocarbons contain adequate amount
of hydrogen to carbon. Each carbon in alkane molecule shares four (4) pairs of
electrons to form four single covalent bonds. The alkanes form a homologous series.
A homologous series is a series of compounds in which each member differs from
next member by a constant amount and the members are called homologs.
ALKANES or PARAFFINS (Cn H2n + 2 )
Phase at Melting Point Boiling Point
NAME FORMULA Room Temp. (0C) . (0C)
Methane CH4 Gas -183 -162
Ethane C2H6 Gas -172 - 89
Propane C3H8 Gas -190 -42
Butane C4H10 Gas -135 -1
Pentane C5H12 Liquid -130 36
Hexane C6H14 Liquid -94 69
Heptane Liquid -90 98
Octane Liquid -57 126
Nonane Liquid -51 151
Decane Liquid -30 174
Higher alkanes are alkanes having nine or more carbon atoms. Nonane is the lightest alkane to
have a flash point above 25 °C, and is not classified as dangerously flammable. The term higher
alkanes is sometimes used literally as "alkanes with a higher number of carbon atoms".
At low pressure both propane and butane gets liquefied, hence they form the main components
of LPG.
NOMENCLATURE
1. For straight chain alkane, except for the first four, take the Greek prefix + ANE at the
ending.
2. For branched-chain:
a. Determine the longest continuous chain of carbon atoms in the molecule.
b. Number the carbon atoms of the longest continuous chain consecutively, starting
from the carbon nearest the branching.
c. Name the branch.
• Branched alkanes are also known as Isoparaffins.
Branches:
Alkyl Group
-CH3 methyl -CH2 CH2CH3 propyl
-CH2CH3 ethyl -CH2 CH2 CH2CH3 butyl
Halogens
-Br bromo -F fluoro
-Cl chloro -I iodo
d. If more than one alkyl group is attached- use di, tri, tetra etc.
e. If different alkyl groups are present, name the branches in alphabetical order
Isoalkane:A Compound of six carbon or less in which all except one, form a continuous chain
and the one carbon is attached to the next-to-the-end carbon.
Classes of Carbon and Hydrogen Atoms in Alkane Molecule
1. Primary Carbon ( 10) . Carbon attached to only one carbon atom
2. Secondary Carbon ( 20). Carbon attached to two carbon atoms.
3. Tertiary Carbon ( 30). Carbon attached to three carbon atoms.
• Hydrogen atoms are similarly classified.
• A ( 10) hydrogen is attached to a ( 10) carbon atom.
Isomerism is the phenomenon whereby certain compounds, with the same molecular
formula, exist in different forms owing to their different organization of atoms. The concept
of isomerism illustrates the fundamental importance of molecular structure and shape in
organic chemistry.
Isomers are substances with the same molecular formula but different molecular
structures. Each isomer has its own conformation.
Conformation is the different arrangements of atoms that can be converted into another
by rotation about the single bonds.
Types:
1. Stereoisomers. Isomers that are different from each other only in the way atoms are
oriented in space(but are like one another with respect to which atoms are joined)
2. Diastereomers. Stereoisomers that are not mirror images(superimposable) of each other
3. Enantiomers. Isomers which are mirror images of each other.
4. Geometric Isomers. Diastereomers that owe their existence to hindered rotation about the
double bonds.
• A branched-chain isomer has lower boiling point than a straight chian isomer because
with branching the shape of the molecules tend to approach that of a sphere. The surface
area decreases, intermolecular forces become weak and are over come at a lower
temperature.
Physical Properties of Alkanes:
1. Molecules are held entirely by covalent bonds.
2. Hydrocarbons are non-polar, london forces increase as molecule grows (larger surface
area, stronger intermolecular forces of attraction)
3. IMFA are london forces so alkanes have low melting point and boiling points. The
process of boiling and melting requires overcoming the IMFA. However, boiling and
melting points rise as the number of carbon atom increases.
Chemical Properties:
1. Burn in air or pure oxygen to form CO2 + H2O
2. React with halogens by continuous substitution forming hydrogen derivatives
Ex: CH4 + Br2 CH3Br + HBr
3. Do not react with aqueous solutions.
4. 4. Undergo thermal decomposition. Alkanes with large molecular weight are broken
down into smaller ones by heat.
REACTIONS:
1. Combustion/Oxidation
High temp.
CH4 + 2 O2 CO2 + H2O
2. Halogenation
light
+ Cl2 + H-Cl
X2 : Cl2 ˃ Br2 H2 : 30 ˃ 20 ˃ 10
CYCLOALKANES ( CnH2n). Compounds containing rings of saturated carbon atoms .
Cycloalkanes have higher boiling point and densities than the corresponding alkanes because of
their compact structure.
Cycloalkanes have higher boiling point and densities than the corresponding alkanes
because of the compact structure.
Cyclopropane
Reactions:
1. Addition reaction with hydrogen(Hydrogenation)
80-100oC
+ H2 CH3-CH2-CH3
Ni
2000C
+ H2 CH3-CH2- CH2- CH3
Ni
2. Halogenation( For cyclopropane and cylcobutane only): Addition Reaction
80-100oC
+ Br2 Br- CH2-CH2-CH2-Br
Ni
2000C
+ HBr Br-CH2-CH2- CH2- CH3
Ni
3. Halogenation of Cycloalkanes: Substitution
light
+ Cl2 + HCl
