NORFAZRIN MOHD HANIF

Pharmaceutical Chemistry
School of Pharmacy, MSU

SPH1203
Organic
Chemistry
Lecturers
1. Nik Nur Shamiha Nik Dzulkefli
nik_nurshamiha@msu.edu.my
03-55216473, 012-920 1066
2. Norfazrin Mohd. Hanif
norfazrin_mohdhanif@msu.edu.my , fazrinhanif@gmail.com
03-55216473 , 012-6681072
List of Chapters
1. Introduction To Organic Chemistry
2. Nomenclature & Isomerism
3. Aliphatic Hydrocarbon
4. Cycloalkanes
5. Concept of aromacity
6. Alcohol
7. Ethers
8. Aldehyde & Ketone
9. Carboxylic Acid
10. Amines
11. Heterocyclic Chemistry
SchemeofWork(SOW)
DATE TOPIC ASSIGNMENT TEST

10/02/14 14/02/14
WEEK 1

Topic 1 : Introduction to Organic Chemistry
Lecturer: Fazrin


17/02/14 21/02/14
WEEK 2
Topic 2 : Nomenclature & Isomerism
Lecturer: Fazrin

Practical 1 (A)
(Fazrin)

24/02/14 28/02/14
WEEK 3

Topic 3: Aliphatic Hydrocarbons (Part 1)
Lecturer: Fazrin

Practical 1 (B)
(Fazrin)

03/03/14 07/03/14
WEEK 4

Topic 3: Aliphatic Hydrocarbons (Part 2)
Lecturer: Fazrin
Quiz 1
(Fazrin)
Practical 2 (A)
(Fazrin)

10/03/14 14/03/14
WEEK 5

Topic 4 : Cycloalkanes (Part 1)
Lecturer: Fazrin


Practical 2 (B)
(Fazrin)

17/03/14 21/03/14
WEEK 6

Topic 4 : Cycloalkanes (Part 2)
Lecturer: Fazrin

Practical 3 (A)
(Fazrin)

24/03/14 28/03/14
WEEK 7


Topic 5 : Concept of aromacity (Part 1)
Lecturer: Fazrin

Quiz 2
(Fazrin)
Practical 3(B)
(Fazrin)

31/03/14 04/04/14
WEEK 8
Topic 5 : Concept of aromacity (Part 2)
Lecturer: Fazrin
Assignment

07/04/14 11/04/14
WEEK 9

Mid Sem Exam

14/04/14 18/04/14
WEEK 10
Mid Sem Exam
SchemeofWork(SOW)(contd)

21/04/14 25/04/14
WEEK 11

Topic 6 : Alcohol
Lecturer: Nik Shamiha


28/04/14 02/05/14
WEEK 12

Topic 7 : Ethers
Lecturer: Nik Shamiha

Practical 4 (A)
(Nik)

05/05/14 09/05/14
WEEK 13

Topic 8 : Aldehyde & Ketone
Lecturer: Nik Shamiha
Quiz 3
(Nik)
Practical 4 (B)
(Nik)

12/05/14 16/05/14
WEEK 14

Topic 9 : Carboxylic Acid
Lecturer: Nik Shamiha

Practical 5 (A)
(Nik)

19/05/14 23/05/14
WEEK 15

Topic 10 : Amines (Part 1)
Lecturer: Nik Shamiha
Quiz 4
(Nik)
Practical 5 (B)
(Nik)

26/05/14 30/05/14
WEEK 16

Topic 10 : Amines (Part 2)
Lecturer: Nik Shamiha


02/06/14 06/06/14
WEEK 17

Topic 10 : Heterocyclic Chemistry (Part 1)
Lecturer: Nik Shamiha
Quiz 5
(Nik)
Lab Test
(Nik)

09/06/14 13/06/14
WEEK 18

Topic 10 : Heterocyclic Chemistry (Part 2)
Lecturer: Nik Shamiha


16/06/14 20/06/14
WEEK 19

Revision

23/06/14 04/07/14
WEEK 20 & 21

Final Exam


SPH1203OrganicChemistry
Assessment
Assignment Quiz Practical Lab Test
Mid Term
Exam
Final Exam
5% 10% 10% 5% 20% 50%

1
Assignment


5
Quizzes


5
Practical


1
Lab test


1 Mid Term
Exam


1 Final Exam



Thank you
1-8
SPH 1203 ORGANIC CHEMISTRY

Chapter 1
Introduction to Organic Chemistry
NORFAZRIN MOHD HANIF
Pharmaceutical Chemistry
School of Pharmacy, MSU

1-9
CHAPTER OUTLINE
Introduction
Classification of Organic Compounds
Functional Groups
Electronegativity
Types of Reactions

1-10
1. Introduction - Organic Chemistry
Besides carbon, the most common elements in
organic compounds are hydrogen, oxygen,
nitrogen, sulfur, and the halogens.
All of the preceding elements are non-metals,
therefore organic compounds have covalent
bonding.
Any structural formula that obeys the bonding
rules in the following table probably represents a
possible compound.
A drawn structure that breaks the bonding rules is
unlikely to exist.
1-11
Bonding in Organic Compounds
Besides carbon, the most common elements in
organic compounds are hydrogen, oxygen,
nitrogen, sulfur, and the halogens.
All of the preceding elements are non-metals,
therefore organic compounds have covalent
bonding.
Any structural formula that obeys the bonding
rules in the following table probably represents a
possible compound.
A drawn structure that breaks the bonding rules is
unlikely to exist.
1-12
Numbers and Types of Bonds for
Common Elements in Organic Compounds

Application of the octet rule indicates that these elements should
bond as shown below:
1-13
Identifying Valid & Incorrect
Structural Formulas
An Example
Two structural formulas are shown above.
Which on does not represent a real
compound?
1-14
Identifying Valid & Incorrect
Structural Formulas
An Example
Two structural formulas are shown above.
Which on does not represent a real
compound?
In structure (a) each H and halogen has one
bond, each C has four bonds, and each O has
two bonds.
This is a valid structure.
1-15
Identifying Valid & Incorrect
Structural Formulas
An Example
As we examine (b), we note that each H
has one bond, each C has four bonds, the
N has three bonds, BUT the O has three
bonds.
The O should only have two bonds.
Therefore (b) is not a valid structure.
1-16
Identifying Incorrect Structural Formulas

The structural formula above appears in a
recent chemistry book. Check the number
of bonds to each atom and determine
whether any bonding rules are violated.

1-17
Identifying Incorrect Structural Formulas

This is not a valid
structure for caffeine!
O should have two
bonds, C should
have 4 bonds
Each N should
have 3 bonds
Each C should
have 4 bonds
1-18
Identifying Incorrect Structural Formulas

This is a valid structure for
caffeine!
1-19
2. Classification of Organic Compounds
1-20
Classification of Organic Compounds
Saturated compounds: Open chain compounds in which
carbon atoms of parent chain are bonded with single
bonds are called saturated acyclic compounds. Ex:







1-21
Classification of Organic Compounds
Unsaturated compounds: The open chain organic
compounds in which parent chain contains one or more
carbon-carbon double bonds or triple bonds are called
unsaturated acyclic compounds. Ex:









1-22
Classification of Organic Compounds
Alicyclic compounds: Organic compound that is both
aliphatic and cyclic. They contain one or more all-carbon
rings which may be either saturated or unsaturated, but
do not have aromatic character.For example










1-23
Classification of Organic Compounds
Aromatic compounds: Benzene is the parent aromatic
hydrocarbon. The organic compounds containing one or
more isolated or fused benzene rings and their
functionalized derivatives are called aromatic compounds
or benzenoid compound. For example:








1-24
Classification of Organic Compounds
Alicyclic heterocyclic compounds: The aliphatic cyclic
compounds containing one or more hetero atoms in their
ring are called alicyclic heterocyclic compounds.
For example








1-25
Classification of Organic Compounds
Aromatic heterocyclic compounds: The aromatic cyclic
compounds containing one or more hetero atoms in their
molecules are called aromatic heterocyclic compounds.
Example





1-26
3. Functional Groups
Functional group: an atom or group of atoms
within a molecule that shows a characteristic set
of physical and chemical properties
Functional groups are important for three
reason; they are
1. the units by which we divide organic compounds into
classes
2. the sites of characteristic chemical reactions
3. the basis for naming organic compounds
1-27
Functional Groups
1-28
Functional Groups
1-29
Alcohols
Contain an -OH (hydroxyl) group
General formula : CnH2n+1OH or CnH2n+2O




Ethanol may also be written as a condensed
structural formula
H-C-C-O-H
H
H
H
H
:
:
-C-O-H
Ethanol
(an alcohol)
Functional
group
CH
3
-CH
2
-OH CH
3
CH
2
OH
or
1-30
Alcohols
alcohols are classified as primary (1), secondary (2),
or tertiary (3) depending on the number of carbon
atoms bonded to the carbon bearing the -OH group
CH
3
-C-OH
CH
3
CH
3
CH
3
-C-OH
CH
3
H
CH
3
CH
3
CH
3
-C-OH
A 1 alcohol A 2 alcohol A 3 alcohol
1-31
Alcohols
there are two alcohols with molecular formula C
3
H
8
O
CH
3
CH
2
CH
2
OH
CH
3
CHCH
3
OH
H-C-C-C-O-H
H
H
H
H
H
H
C-C-C-H
H
H
OH
HH H
H
or
or
a 2 alcohol
a 1 alcohol
1-32
Amines
General formula : CnH2n+1NH2
Contain an amino group; nitrogen bonded to one,
two, or three carbon atoms
an amine may by 1, 2, or 3
C H
3
N H
H
C H
3
N H
C H
3
C H
3
N

C H
3
C H
3
Methylamine
(a 1 amine)
Dimethylamine
(a 2 amine)
Trimethylamine
(a 3 amine)
:

:

:

1-33
Aldehydes and Ketones
General formula aldehydes: CnH2nO
General formula ketone : CnH2nO
Contain a carbonyl (C=O) group
C H
O
CH
3
-C-H
O
CH
3
-C-CH
3
O
C
O
Functional
group
Acetaldehyde
(an aldehyde)
Acetone
(a ketone)
Functional
group
1-34
Carboxylic Acids
General formula : CnH2nO2 or CnH2n+1COOH
Contain a carboxyl (-COOH) group
C O
O
H CH
3
-C-O-H
O
CH
3
COOH CH
3
CO
2
H
: :
:
:
or or
Acetic aci d
(a carboxyli c acid)
Functional
group
1-35
Carboxylic Esters
Ester: a derivative of a carboxylic acid in which
the carboxyl hydrogen is replaced by a carbon
group
General formula : CnH2nO2
C O
O
Functional
group
CH
3
-C-O-CH
2
-CH
3
Ethyl acetate
(an ester)
:
:
: :
O
1-36
Carboxylic Amide
Carboxylic amide, commonly referred to as an
amide: a derivative of a carboxylic acid in which
the -OH of the -COOH group is replaced by an
amine




General formula : CnH2n+1CONH2

CH
3
-C-N-H
H
Acetamide
(a 1 amide)
O
C N
O
Functional
group
1-37
4. Electronegativity
Electronegativity:
a measure of the force of an atoms attraction of
electrons that is shares in a chemical bond with
another atom.
1-38
Electrophile And Nucleophile
Reagents in organic reactions can be classified either
electrophiles or nucleophiles depending on whether they
attack regions of high electron density (-) or regions of
low electron density (+).
regions of low electron density (+) also known as
electron-deficient sites.
Electrophiles:
- a species (ion or molecule) which attacks by a negatively
charged carbon atom by accepting an electron pair.
- Lewis acid
-positive ions or molecule that have an electron-deficient
atom (+).
- known as electrophilic reagents
1-39
Electrophile And Nucleophile
Nucleophile:
- a species (ion or molecule) that attacks a positively
charged carbon atom by donating an electron pair to
form a dative covalent bond.

- known as nucleophilic reagents

- Lewis bases

- negative ions or molecules that have at least one
lone pair of electrons.
1-40
Examples of nucleophiles and electrophiles
OH, RO
C
R-OH
C C
H
2
O
C
+
RN
2
+
BF
3
AlCl
3
CN
-
nucleophiles
(donors of electron pairs)
electrophiles
(acceptors of electron pairs)
CI, Br, I
(carbanion)
NH
3
, RNH
2
Reducing agents
Oxidising agents
H
+
(or H
3
O
+
), NO
2
+
(nitronium ion)
Cl
2
, Br
2
(carbocation)
FeBr
3
, ZnCl
2
Cl
+
, Br
+
, I
+
1-41
Examples of nucleophiles and electrophiles
CH
3
N
H
H
CH
3
CH
2
Cl
CH
3
N
H
H
CH
2
CH
3
Cl
nucleophile electrophile
+
-
1-42
5. TYPES OF REACTIONS
Substitutions
Additions
Eliminations
Rearrangements

1-43
SUBSTITUTION REACTIONS
Substitutions are the characteristic reactions of saturated
compounds such as alkanes and alkyl halides, and of
aromatic compounds (even though they are unsaturated).
In a substitution, one group replaces another.
For example, methyl chloride reacts with sodium
hydroxide to produce methyl alcohol and sodium
chloride:
In this reaction a hydroxide ion from sodium hydroxide
replaces the chlorine of methyl chloride.

1-44
ADDITIONS REACTIONS
Additions are characteristic of compounds with multiple
bonds. Ethene, for example, reacts with bromine by an
addition. In an addition all parts of the adding reagent
appear in the product; two molecules become one.


1-45
ELIMINATIONS REACTIONS
Eliminations are the opposite of additions. In elimination
one molecule loses the elements of another small
molecule. Elimination reactions give us a method for
preparing compounds with double and triple bonds.
Eg: Dehydrohalogenation, a reaction that is used to
prepare alkenes. In dehydrohalogenation, as the word
suggests, the elements of a hydrogen halide are
eliminated. An alkyl halide becomes an alkene:
1-46
REARRANGEMENT REACTIONS
In a rearrangement a molecule undergoes a
reorganization of its constituent parts. For example,
heating thefollowing alkene with a strong acid causes the
formation of another isomeric alkene.
In this rearrangement not only have the positions of the
double bond and a hydrogen atom changed but a methyl
group has moved from one carbon to another.
1-47
THANK YOU!