REVIEW OF

ORGANIC CHEMISTRY
Jose Philip G. Maglalang, RPh

J.P Maglalang, RPh

PHARMACEUTICAL BIOCHEMISTRY

Learning Objective/s
• To be able to understand and familiarize the
different concepts in Organic Chemistry

J.P Maglalang, RPh

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INTRODUCTION

ORGANIC CHEMISTRY

• A chemistry of carbon compounds.

• But not all carbon compounds are
organic.
• Carbonate (CO32-), Cyanide (CN-),
Bicarbonate (HCO3-), Carbon dioxide (CO2)
and Carbon monoxide (CO).

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PROPERTIES OF TYPICAL ORGANIC AND INORGANIC
COMPOUND
Property Organic compound Inorganic compound
Bonding with molecule Usually, covalent Often ionic
Generally weak Quite strong
Forces between molecules
(Intermolecular force) (Electrostatic force)
Gases, liquids or low melting- Usually high melting-
Normal physical state
point solids point solids
Flammability Often flammable Usually, nonflammable
Solubility in water Insoluble Soluble
Conductivity Non - conductor Conductor
Rate of chemical reaction Slow and complex Fast and simple

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TYPES OF ORGANIC COMPOUND

ACYCLIC OR ALIPHATIC COMPOUNDS

• Molecules have chains of carbon atoms

but no rings. the chains may be
unbranched or branched.
• Saturated compounds that only contain
single bond
• Unsaturated compounds that contain
double or triple bond

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TYPES OF ORGANIC COMPOUND

ALICYCLIC OR CYCLIC COMPOUNDS

• Close chain of carbon atoms

• Rings form the shape of POLYGON
(triangle, square, rectangle or etc.)
• Carbocyclic or Homocyclic
compounds contain rings of carbon atoms
• Heterocyclic compounds contain at
least one atom in the ring must be a
heteroatom, an atom that is not carbon.

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TYPES OF ORGANIC COMPOUND

AROMATIC/ARENE COMPOUNDS

• Hydrocarbons which contain benzene,

or some other related ring structure.

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FUNCTIONAL GROUPS

FUNCTIONAL GROUPS

• An atom or group of atoms which

determine the chemical and physical
properties of an organic compound

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IMPORTANCE

THEY ARE THE UNITS BY WHICH WE

DIVIDE ORGANIC COMPOUNDS INTO
CLASSES

THEY ARE THE SITE OF CHEMICAL

REACTION

SERVES A BASIC NAMING OF ORGANIC

COMPOUNDS

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FUNCTIONAL GROUPS

J.P Maglalang, RPh

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FUNCTIONAL GROUPS

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FUNCTIONAL GROUPS

ALKYL GROUP CARBONYL GROUP

• A functional group of an organic chemical • Functional group composed of a carbon
that contains only carbon and hydrogen atom double-bonded to an oxygen atom
atoms

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FUNCTIONAL GROUPS

HYDROXYL GROUP CARBOXYL GROUP

• Functional group consisting of an oxygen • Functional group consisting of a carbonyl
atom with two lone pairs bonded to a group with a hydroxyl group
hydrogen atom.

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NAMING OF FUNCTIONAL GROUPS

IDENTIFY THE LONGEST CARBON CHAIN

CONTAINING THE HIGHEST-ORDER
FUNCTIONAL GROUP

NUMBER THE CHAIN

NAME THE SUBSTITUENTS

ASSIGN A NUMBER TO EACH

SUBSTITUENT

COMPLETE THE NAME

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EXERCISE
Give the IUPAC or COMMON NAME, and Identify what of functional group in given chemical formulas.

1 3
5

2,2,4-trimethylpentane propanone (acetone)

benzenecarboxylic
2 acid (benzoic acid)
4

p-nitrophenol methyl ethanoate (methyl acetate)

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STRUCTURAL FORMULA

KEKULE FORMULAS

• A Lewis structure in which bonded

electron pairs in covalent bonds are
shown as lines.
• Kekulé was the first to suggest a
sensible structure for benzene.

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STRUCTURAL FORMULA

CONDENSED FORMULA

• To save space and time in the

representation of organic structures, it
is common practice to use "condensed
formulas" in which the bonds are not
shown explicitly.

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STRUCTURAL FORMULA

3D STRUCTURAL FORMULA

• This shape is dependent on the

preferred spatial orientation of
covalent bonds to atoms having two or
more bonding partners
• Three dimensional configurations are
best viewed with the aid of models.

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STRUCTURAL FORMULA

SKELETAL FORMULA

• Line-Angle Formula
• A two-dimensional representation of
molecular entities in which atoms are
shown joined by lines representing
single or multiple bonds, without any
indication or implication concerning
the spatial direction of bonds

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STEREOCHEMISTRY

STEREOCHEMISTRY

• The branch of chemistry concerned

with the three-dimensional
arrangement of atoms and molecules
and the effect of this on chemical
reactions.
• IMPORTANT NOTES TO TAKE:
• We need at least one sp3-
hybridized carbon

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STEREOCHEMISTRY

ISOMERS

• Two or more compounds with the

same molecular formula but a different
arrangement of atoms in the molecule
and different properties.

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THEY CAN DIFFER IN

ARRANGEMENT OF BONDS

CONFIGURATION

CONFORMATION

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ISOMERS

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ISOMERS

STRUCTURAL / CONSTITUTIONAL
ISOMERS
• Compounds with same molecular
formula but different in arrangement
or connectivity

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STRUCTURAL / CONSTITUTIONAL ISOMERS

Skeletal / Chain Positional Functional

Same molecular formula Same molecular formula Same molecular formula
Different in structure Different in structure Different in structure
Different in parent name Same in parent name Different in functional group
Different in branching Different in branching

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ISOMERS

STEREOISOMERS

• Have the same molecular formula and

connectivity of atoms in their
molecules, but different 3D orientation
of their atoms in space

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STEREOISOMERS

CONFORMATIONAL ISOMERS /
CONFORMERS
• Stereoisomerism in which the isomers
can be interconverted just by rotations
about formally single bonds about σ
bonds.
• Temporary difference

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STEREOISOMERS

CONFIGURATIONAL ISOMERS

• Two molecules with the same

constitution but different configuration
and the isomers cannot be
interconverted without breaking and
remaking covalent bonds.
• Permanent difference

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CONFIGURATIONAL ISOMERS

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CONFIGURATIONAL ISOMERS

GEOMETRIC

• Isomers in which the order of atom

bonding is the same but the
arrangement of atoms in space is
different.
• Cis isomer atoms on the same side of the
molecule
• Trans isomer atoms has on opposite
sides of the molecule

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CONFIGURATIONAL ISOMERS

OPTICAL

• Molecule can exist as two isomers that are

non-superimposable, mirror image of each
other
• They have same physical properties, but they
rotate polarized light in opposite direction
• Enantiomers - Two molecules that are
nonsuperimposable mirror images of each
other
• Diastereomers - non-mirror-image,
nonsuperimposable configurational
isomers
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SUMMARY

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ORGANIC REACTIONS
OXIDATION
• The replacement of C - H bonds by C – O
• Decrease in the number of carbon-hydrogen
bonds.

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ORGANIC REACTIONS

REDUCTION
• The replacement of C - O bonds by C – H

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ORGANIC REACTIONS

HYDROGENATION
• Addition pairs of hydrogen atoms to a
compound

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ORGANIC REACTIONS

HYDROLYSIS
• The cleavage of chemical bonds by the
addition of water

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ORGANIC REACTIONS
HALOGENATION
• Reaction of a compound with a halogen and
results in the halogen being added to the
compound

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ORGANIC REACTIONS

ESTERIFICATION
• Process of combining an organic acid
(RCOOH) with an alcohol (ROH) to form
an ester (RCOOR) and water

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ORGANIC REACTIONS

SUBSTITUTION
• Chemical reaction during which one
functional group in a chemical
compound is replaced by another
functional group.

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SUBSTITUTION REACTIONS

NUCLEOPHILE
• Reactant that donates a pair of
electrons to form a new covalent bond

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SUBSTITUTION REACTIONS

LEAVING GROUP
• An atom or group of atoms which
breaks away from the rest of the
molecule

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SUBSTITUTION REACTIONS

SUBSTRATE
• Chemical of interest that is being
modified

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SUBSTITUTION REACTIONS
1. FORMATION OF A CARBOCATION

SN1 MECHANISM
• Substitution Nucleophilic Unimolecular
• Overall rate of this reaction depends on one 2. NUCLEOPHILIC ATTACK
molecule, the substrate losing its leaving group
• Attack of nucleophile from the back side or
front side

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SUBSTITUTION REACTIONS

SN2 MECHANISM
• Substitution Nucleophilic Bimolecular
• Reaction rate will depend on two molecules
coming together
• There is no carbocation is involved and the
nucleophile plays much active role
• Attack of nucleophile from the back side
• 2 steps

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REFERENCES

• Hart, H., Craine, L. E., & Hart, D. J. (1999). Organic

chemistry: A short course. Boston: Houghton
Mifflin Co.
• Stoker, H. (2012). General, Organic and Biological
Chemistry, 6 th Ed.

J.P Maglalang, RPh