REACTIONS IN

ORGANIC CHEMISTRY
Created by Gab Paragas for
University of Santo Tomas
SCHOLIA TUTORIAL CLUB
(Preliminaries 2012)

Note to Reviewees
This PowerPoint presentation is an intellectual
property of Ramoncito Gabriel O. Paragas of UST
Pharmacy. This was created to aid in the review of
fellow Pharmacy, Med Tech, and Biochem students
taking the course. This presentation is not definitely
complete, and is not a substitute to self-study and
note taking. This is created for Scholia Tutorial Club.
Any unauthorized and improper use of this
presentation is prohibited.

What Well Talk about in a

while

Last exams, we reviewed about introductions to

organic chemistry. This preliminaries, we will go a
little bit deeper on the different reactions organic
compounds go through. If you will, we will discuss
the following:
Stereochemistry of Organic Compounds. We will
discuss the handedness of organic compounds. We
will encounter the terms enantiomers and
chirals.
The nature of Organic Reactions (Alkenes and
Alkynes). What makes these compounds react?
Reactions of Alkenes and Alkynes

What to expect from the

exam

Describing reactions through energy

diagrams
Web or Reaction Maps
Predictions of Reactants, Reagents
and Catalysts, Products and
Reactions
Index of Hydrogen Deficiency (IHD)
calculation
Ready?

Mind Map
Nature
Orgof
Reactions
Organic of
Reactions
Organic Compounds

Review of Fundamental
Concepts

Refresh!
From the last
powerpoint
and review
session, we
have
discussed
about multiple
bonds
between
Carbon atoms.
Lets review.

Alkenes, are also called olefins; they are

hydrocarbons that contain a carbon-carbon
double bond, C=C. They are sp2-sp2
hybridized, meaning they have 33.3% s
character, 66.6% p character. They have one
sigma bond (internally shielded), and one pi
bond (overlap, external, and weak). The pi
bond has pi electrons that attack
electrophiles, making alkenes nucleophiles.

Refresh!

Alkynes, on the other hand are

hydrocarbons that contain a carboncarbon triple bond, C=C. They are sp-sp
hybridized, with 50% s character, and
50% p character. They have one sigma,
two pi bonds. The more pi, where a
maximum of two is possible per carboncarbon, the more pi electrons.
Can YOU give some examples of
olefins and alkynes?

Refresh!

Commonly, from the last grading, we hear the term

aromatic. Aromatics are compounds that possess
characteristic smell, thus the name from the term aroma.
Generally, aromatics follow the following criteria:
Cyclic (interconnected Carbons and Other Atoms)
Have conjugated pi bonds (not cumulative or
successive), meaning they (pi) are alternate.
Follow Hckels rule which is Number of electrons =
4n + 2. n is the indicator of aromaticity, where it should
be a WHOLE NUMBER. If n is not whole, the compound is
non-aromatic. Tip: You can find the number of pi
electrons by counting the pi bonds multiplied to
two.

Refresh!

Is the figure below an aromatic compound?

Is it cyclic? YES.
Are the pi bonds conjugated/ non-successive? YES.
Does it follow Hckels rule? NO.
4 pi electrons = 4n + 2
4n = 2
n = (NOT A WHOLE NUMBER.)

Now What about

Nucleophiles and Electrophiles?
The very concept of electron transfer must be understood better
to proceed to the next topics with confidence. A lot of students
do not understand the philes, or lovers of chemistry. Well here
they are.

Nucleophiles, (n) are nucleon-loving compounds. Nucleons

are the protons and neutrons lying inside the nucleus of an
atom. Given that they are nucleon-loving, they are electrically
and chemically attracted with protons (+) or positively charged
atoms.
Has a negatively polarized electron-rich atom. When you see dots
around the compound like the one above , it is electron-rich,
nucleophilic. Tip: the more sigma bonds, the more nucleophilic.
Forms a bond by donating electron pair.

Now What about

Nucleophiles and Electrophiles?

Electrophiles (e+), from the name are

electron loving compounds or
atoms.

They are e- poor (electron poor),

meaning they lack electrons and they
want to have some. This is satisfied by
bond formation.
Has a positively polarized electronpoor atom.
Forms a bond by accepting an
electron-pair. Tip: When you can see a +
sign, or incomplete or missing dots around

Now What about

Nucleophiles and Electrophiles?

Take a look at the illustration below to

better understand nucleophiles and
electrophiles.

Mechanism of
Neuclophile-Electrophile Interaction

Observe the e- transfer from the

illustration.

Which is the Nucleophile, the Electrophile?

From where did the electrons transfer?
What product is formed?

Kinds of Organic Reactions

Now that we have learned about alkenes and
alkynes, let us now tackle their chemical reactivity.
Organic Chemical Reactions can be organized
either by what kinds of reactions occur or by how
these reactions occur. There are four reactions we
would tackle, but we may also add one more.

Addition Reaction
Elimination Reaction
Substitution Reaction
Rearrangement Reaction, and
Redox (Reduction-Oxidation) Reaction

Kinds of Organic Reactions

Addition Reaction occurs with two

reactants adding together to form
one single product with no leftover
atom, meaning, all are used up.

Kinds of Organic Reactions

Elimination Reaction however is the

opposite of addition reaction. It
occurs when an organic reactant
(one) splits down to two separate
products. A bunch of factors is
responsible for this. This includes
catalysts (acids, etc), initiators (UV,
light) and even solvents.

Kinds of Organic Reactions

Substitution Reaction, from its name

occurs when two reactants exchange
partners to give to new products.
The parts substitute each other to form
new different products. It goes like this:
A and B are in a relationship but they
broke up. A found C, so for B to get
back at A, B befriends D to make A
jealous. The Example below is the
chlorination of methane.
AB + CD AC + BD

Kinds of Organic Reactions

Rearrangement Reaction occurs when

a reactant undergoes some twists or
reorganization of bonds and atoms
to give the isomeric products (same
formula, different structure). The above
photo is the general rearrangement
scheme of reaction.

Kinds of Organic Reactions

Although not taught by some professors, let us take a look

at this fifth reaction, Redox.
Redox Reaction is the simultaneous reductionoxidation of and organic compound when an agent is
added to it. Mostly, these agents are above the arrow or
yield sign to indicate that they do not fully interact with
the organic compound. The general considerations are
as follows:

If by any case you INCREASE THE H (Hydrogen) in the

compound, the product was reduced. This is
accompanied by the DECREASE OF C, O, N, S, Se,
Halogen bondings.
If the case is the INCREASE OF OXYGEN, OXIdation
occurred.

Its a matter of Make-orBreak

Now, as these reactions progress,

there comes the process of bondbreaking and making for a product to be
formed.
Bond Breaking (-lysis) is the
breaking or cleaving of atomic
bonds to separate the components.

A HOMOLYTIC/ RADICAL bond-breaking

is when a bond breaks, the two atoms get
a fair and equal share of the valence/
outer electrons. Homo means share.

Its a matter of Make-orBreak

Bond Breaking (cont.)

A HETEROLYTIC/ POLAR bond breaking occurs when

one of the two atoms gets everything/ something
and the other gets nothing and loses something.
Hetero means solo. Take a look at the illustration:

Note:

A heterolytic bond breaking is polar because it

produces products with charge, or a positive and
negative pole. B gets all the valence e-, so it gets more
electrons, so more negative. The one left must be
positive. Its like this: the one left by someone should
become positive in thinking and must move on.

Its a matter of Make-orBreak

Bond-making (-genesis) is the

making or forming of bonds
between atoms to form a stable
product.

A HOMOGENIC/ RADICAL bond-making

is the symmetrical bond formation
where both atoms give an electron for
sharing.

A HETEROGENIC/ POLAR bond-making

occurs when only one gives electrons
for sharing and the other just takes.

Nature of Organic
Reactions

Mechanisms of Organic
Reactions

We have discussed in the recent

slides the processes required for
reactions to proceed. The following
processes are:
Bond-Breaking
Nucleophilic electrons attack to
Electrophile
Bond-Making
Now, lets take focus on the
heterogenic/polar reaction of
organic compounds to better

Making the Transition

The reaction above describes the polar/

heterogenic bond-making between the H-Cl
atoms to the ethylene atoms. We notice that
the pi electrons from the pi bond of the
ethylene attacks the Hydrogen of HCl. This
tells us that ethylene is the nucleophile, and
HCl is the electrophile.

Making the Transition

The attack then forces bond breaking between

the H-Cl, where the bond (possessing electrons)
all join the Cl. There is a heterolysis.
Come to notice, if the electrons of the bond of
ethylene attacks the H, it leaves one C, so the
one left becomes positive. Same for the H, where
Cl takes all the electrons.

Making the Transition

So you may ask me, what happens next?

The positive charge of one carbon (carbocation,

carbon with +) then attracts the negative charge
of chloride, same as the positive charge of H
attracted the pi electrons of ethylene. The Product
then becomes an alkane; a hydrohalogenated
alkane to be exact.

Making the Transition

Contrary to what others suppose, organic
reactions do not proceed in a snap. They happen
step by step, blow by blow, one make and
break at a time.
We notice in the past example that there is a
transition state. Before ethylene, an alkene
became an alkane chloroethane, first became
positively charged, thus the name CARBOCATION
(CARBO=carbon; CATION=positive charge). The
bracketed state is called the transition state. The
compound inside the bracket is called the
CARBOCATION INTERMEDIATE.

Mechanism of Reaction

The Graphic Interpretation:

Energy Diagram
The diagram in the
right is called an
energy diagram. It is
a pictorial
description of a
reaction, following the
course of reaction
from reactant to
product. This actually is
the energy diagram
of the Ethylene plus
HCl reaction.

The Graphic Interpretation:

Energy Diagram

An energy diagram for

the reaction of ethylene
with HCl. Two separate
steps are involved,
each with its own
activation energy,
transition state, and
energy change. The
energy minimum
between the two steps
represents the
carbocation reaction
intermediate.

The Graphic Interpretation:

Energy Diagram
Parts of the diagram:
Axes: Energy and
Reaction Progress.
A. Reactants Phase
B. First Transition
state, where the
distance between A
and B is the
Activation energy
Eact

C. The Carbocation
intermediate

The Graphic Interpretation:

Energy Diagram
Parts of the diagram
(cont.):
D. Second Transition
state where the
carbocation attracts
Cl E. The Product and
Stable phase
F. Overall energy
change, where the final
energy state is
subtracted from the
initial.

The Graphic Interpretation:

Energy Diagram
So what can we
infer from the
diagram?
How many steps
are there?
Is the reaction
fast or slow?
Is it endothermic
or exothermic?
Is it favorable?

The Graphic Interpretation:

Energy Diagram
So what can we infer
from the diagram?
How many steps
are there? (TWO)
Is the reaction fast
or slow? (SLOW)
Is it endothermic or
exothermic? (EXO)
Is it favorable? (FAV)

The Graphic Interpretation:

Energy Diagram

How did we know those things with just a

diagram?
Number of steps is determined by counting
the number of peaks in the diagram. The
peaks tell us of energy changes that accompany
reactions.
Speed of reaction is determined by the
length of distance between A and B, or
deeper, the amount of energy needed to
reach B from A. The longer the distance, the
slower the reaction. Like climbing a mountain,
the higher the peak, the slower you can reach it.

The Graphic Interpretation:

Energy Diagram

How did we know those things with just a diagram?

(cont.)
Heat flow is determined by the value of energy of
the reactants versus the products. In the
diagram, the products have lower energy
requirement compared to the reactant phase.
Thus it is exothermic because it releases heat,
and reaches stability with lower energy.
Favorable or not, if the reaction is exothermic, it
is favorable. Lower energy of the product tells
us that the product is stable even on lower
energy than before, and thats what we want.

The Graphic Interpretation:

Energy Diagram
Exercise: Draw a diagram with the
following data.
Two Step
Fast
Endothermic and Unfavorable
Exercise: Interpret the table below,
and determine the parts of the
diagram.
How many steps?
Label the steps, which is fastest?

Catalysis
Speed of reaction depends in so many
factors. However, a positive speed
change is achieved biochemically by
enzymes. As pharmacists, medical
technologists and biochemists, we
should know the difference of catalyzed
reactions with non-catalyzed. Catalyzed
reactions are generally faster. Enzymes
are biological catalysts. They help aid
metabolic processes and many body
functions.

Catalysis

An energy diagram for

a typical, enzymecatalyzed biological
reaction (blue curve)
versus an uncatalyzed
laboratory reaction
(red curve). The
biological reaction
takes place in several
steps, each of which
has a relatively small
activation energy.

Catalysis
So what can we
infer from the
diagram?
How many steps
are there?
Is the reaction
fast or slow?
Is it endothermic
or exothermic?
Is it favorable?

Reactions of Organic Compounds

A Brief Note

Before we begin discussing organic reactions, we

want to briefly discuss some things with you.
This next chapter is all about memorization.
As much as you have to know the mechanisms
by heart, you also have to know and memorize
by heart the reactions themselves. We may
teach you these, but the sole success of
knowing these things may depend on you.
The memorization is on your shoulders.
Things to Highlight: Process, Reagents and
Products of the Organic Reactions.

MARKONIKOV RULES!

Nah.. Its actually Markonikovs rule.

To tell you the truth, I was kind of
bored and intrigued by the many
complex definitions of Markonikovs
rule. Let me however rephrase the rule
to a simpler and more relatable concept.
Markonikovs rule is a rule of
socializing. It basically is a rule for
Hydrogen, where Hydrogen doesnt
want to be out-of-place nor crowded
because hes claustrophobic.

MARKONIKOV RULES!

Markonikovs rule is a rule of

socializing. It basically is a rule for
Hydrogen, where Hydrogen doesnt want
to be out-of-place nor crowded because
hes claustrophobic.
Take a look at the basic example of
vinylchloride.
H2C=CHCl + H-Br
?
Where will the RED H go? To the YELLOW
C, or the GREEN C?
What about the BLUE Br?

MARKONIKOV RULES!

H2C=CHCl + H-Br
?
Where will the RED H go? To the YELLOW
C, or the GREEN C? (To the Yellow C)
What about the BLUE Br? (The blue Br
will go to the Green C)
H Br
Product: H C C H
H Cl
Remember your steric effects.

Stability

To better understand Markonikovs Rule,

take a look at the illustration:

The illustration tells us that whenever

possible, we must produce a product
that is Tertiary or Secondary. This guides
us in determining if the product we formed is
favorable or not, most likely to happen
or not.

Reactions of Alkenes

Lets divide the reactions to three. It is much

easier to memorize when you know that
some reactions belong together.
Electrophilic Addition. The alkene is the
NUCLEOPHILE, and its pi electrons attack
the ELECTROPHILE.
Oxidation. Basically, addition of Oxygen
by oxidizing agents such as KMnO4
Polymerization. Repetitive addition of
small identical monomer units.

Electrophilic Addition
1. Hydrohalogenation (HX)

Reagents:
Alkene plus
HX (where H is
Hydro, X is any
Halogen: Cl, Br, I)
Ether (as
solvent)

Mechanism:
Follows
Markonikovs
Rule
(Regiospecific)
Product:
Alkylhalide

General Reaction Scheme:

Examples:

Electrophilic Addition
2. Hydration (H2O)

Reagents:
Alkene plus
H2O
Acid Catalyst
(H2SO4, H3PO4)
under blah-blah
conditions

Mechanism:
See Next slide
Acid lends Proton
Syn-addition
(same side)
Product: Alkyl
Alcohol

General Reaction Scheme:

Examples:

Electrophilic Addition
2. Hydration (H2O)

Electrophilic Addition
3. Halogenation(X-X)

Reagents:
Alkene plus
X-X (where X is
X2; Cl or Br)
Solvent
General Reaction Scheme:

Mechanism:
Antistereochemis
try (where it is
not steric effectsensitive)
Product: Dihaloalkane
Examples:

Electrophilic Addition
4. Hydrogenation/ Reduction (H-H)

Reagents:
Alkene plus
H-H or H2
Needs a Metal
Catalyst (PtO2
or Pd/C)
General Reaction Scheme:

Mechanism:
See next slide
H-H adsorbs to
the catalyst, and
disentegrates
Product: Alkane
Examples:

Electrophilic Addition
4. Hydrogenation (H-H)

Oxidation
1. Epoxidation (Epoxy = Cyclic Ether)

Reagents:
Alkene plus
Epoxidizing
agent (such as
Carboxylic Acid)
General Reaction Scheme:

Mechanism:
Epoxidation, or
addition of
epoxidizing agent
Product:
Epoxide/Oxiran
e
(3-Membered ring, with O )
Examples:

Oxidation
2. Hydroxylation (with KMnO4)

Reagents:
Alkene plus
KMnO4 in Basic
Medium (NaOH)
General Reaction Scheme:

Mechanism:
Two OH groups will
attach to the original
site of the double bond
Syn addition (same
side)

Product:
Alkanediol
Examples:

Oxidation
3. Strong Oxidation (with KMnO4)

Reagents:
Alkene plus
KMnO4 in Acidic
Medium (H3O+)
General Reaction Scheme:

Mechanism:
Oxidative
Cleavage
Product: Two
possible
Two ketones (if
4 Rs)
One ketone,
one CO2
Examples:

Polymerization:
Radical Addition of to Alkenes

Reagents:
Alkene
Polymerized by
addition of
monomers
General Reaction Scheme:

Mechanism:
Initiation
Propagation
Termination
Product:
Polymer
Examples:
See next Slide.

Polymerization:
Radical Addition of to Alkenes

STEP 1 Initiation: The polymerization reaction

is initiated when a few radicals are generated on
heating a small amount of benzoyl peroxide
catalyst to break the weak O-O bond. A
benzoyloxy radical then adds to the C-C bond of
ethylene to generate a carbon radical. One
electron from the carboncarbon double bond
pairs up with the odd electron on the benzoyloxy
radical to form a C-O bond, and the other
electron remains on carbon.

Polymerization:
Radical Addition of to Alkenes

STEP 2 Propagation: Polymerization occurs

when the carbon radical formed in the initiation
step adds to another ethylene molecule to yield
another radical. Repetition of the process for
hundreds or thousands of times builds the
polymer chain.

Polymerization:
Radical Addition of to Alkenes

Termination: The polymerization process is

eventually ended by a reaction that consumes
the radical. Combination of two growing chains is
one possible chain-terminating reaction.

Ethylene is not unique in its ability to form a

polymer. Many substituted ethylenes, called vinyl
monomers, undergo polymerization, yielding
polymers with substituent groups regularly spaced
along the polymer chain. Propylene, for example,
yields polypropylene.

Reactions of Alkynes

Reactions of Alkynes

Reactions of Alkynes

Reactions of Alkynes

Reactions of Alkynes

Reactions of Alkynes

Reactions of Alkynes

Alkane Reactions

The main type of reaction for alkanes

is substitution. Presence of initiator is as
well needed. Alkanes are strong and
stable, so it takes special conditions
before they can react. Initiators may
include UV or any Light.
Example:

Aromatic Reactions

Aromatic Reactions
So let us introduce to you the reactivity of
aromatic compounds. In General Organic
Chemistry, we are only talking about Benzene
(C6H6), and sometimes Naphthalene (C10H8).
In the last powerpoint presentation, we have
emphasized to you that resonance makes a
benzene ring stable. Anything that is stable
is hard to react with, because they want to
remain stable. It takes special conditions
before aromatics react, and attain once
more stability.

Aromatic Reactions: Substitution

1. Nitration

Reagents:
Benzene +
HNO3
H2SO4
General Reaction Scheme:

Mechanism:
As illustrated
Product:
Nitrobenzene
Examples:

Aromatic Reactions: Substitution

2. Sulfonation

Reagents:
Benzene +
SO3
H2SO4
General Reaction Scheme:

Mechanism:
As illustrated
Product:
Benzenesulfonic
Acid
Examples:

Aromatic Reactions: Substitution

3. Bromination

Reagents:
Benzene +
Br-Br
FeBr3 Catalyst
General Reaction Scheme:

Mechanism:
See Next Slide
Product:
Bromobenzene
Examples:

Aromatic Reactions: Substitution

3. Bromination

Aromatic Reactions: Substitution

4. Halogenation (Chlorination, Iodin)

Reagents:
Benzene +
X-X (Cl, I)
FeCl3 or FeI3
Catalyst
General Reaction Scheme:

Mechanism:
As illustrated
Product:
Halobenzene
Examples:

Friedel-Crafts AlkylationAcylation

Yes, these two geniuses discovered the process.

Today, in the industry, alkylation and acylation of
aromatics are two of the most useful processes
of electrophilic aromatic substitution. Alkylation
is done by the introduction of an alkyl to replace
one H around the benzene ring. Acyl means
Carboxylic Acid Chloride, thus acylation is the
introduction of carboxylic acid chloride
(RCOOCl), or acid anhydride.
Remember: It is crucial to remember that only
the Friedel-Crafts Aromatic Reactions utilize
Aluminum-halide catalysts.

Friedel-Crafts Alkylation

General Reaction Scheme:

Friedel-Crafts Acylation

Closely related with the alkylation, it has

the same mechanism, but different
reagents.
Example:

General Reaction Scheme:

Reduction of Benzene: Hydrogenation

If the Benzene Ring is introduced

with Hydrogen Gas (H-H), take note:
THERE IS NO REACTION. The reason is
the inertia/ inert character of benzene,
and the pressure requirements of H2
H2
No Reaction (NR)
If however, Benzene reacts with H-H
under some blah-blah conditions,
or any condition regarding pressure, a
reaction occurs, producing

Reduction of Benzene: Hydrogenation

H2

No Reaction (NR)
If however, Benzene reacts with H-H under
some blah-blah conditions, or any condition
regarding pressure, a reaction occurs, producing
cyclohexane.

Exam Technique: If you see any blah-blah

conditions, let the reaction proceed by copying the
whole structure without the aromatic ring.

Oxidation of Benzene:
KMnO4

Same as Reduction/ Hydrogenation of the Benzene

ring, Benzene will not react as well with KMnO 4, a
strong oxidizing agent, under simple conditions.
KMnO4
No Reaction
Only with Water, will benzene react with and oxidant.
Benzoic Acid is always the product.
Exam Tip: Aromatic Redox is really tricky. Always
remember that only at blah-blah conditions,
benzene is reduced, oxidized. Dont get confused!

Classification of Substituent Effects in

Electrophilic Aromatic Substitutions

Directing Deactivators and Activators tell

us of the probability of positions
around the benzene ring. When your
benzene ring is already substituted
and an electrophile reacts again to
it, the diagram below helps you
determine the final structure to
achieve stability, based on
reactivity. The following positions are
Ortho (1,2), Meta (1,3) and Para
(1,4).

Classification of Substituent Effects in

Electrophilic Aromatic Substitutions

Substituent effects in electrophilic aromatic

substitutions. All activating groups are ortho- and
para-directing, and all deactivating groups other than
halogen are meta-directing. The halogens are unique
in being deactivating but ortho- and para-directing.

Steriochemistry and Regiospecificity

Basics of Stereochemistry
Chiral

Chirals are any compounds with

carbon (chiral center) that has 4
different groups surrounding it.

Achiral

Achirals have two or more

identical groups around its chiral
center. (Carbon that causes
chirality)

To the Left or to the Right?

Configuration is the term used to name the

drawing of specific three-dimensional
representation of a chiral molecule with the
chirality center surrounded by R-groups. Steps
follow:
RULE 1 Look at the four atoms directly attached
to the chirality center, and rank them according to
atomic number. The atom with the highest atomic
number has the highest ranking (first), and the
atom with the lowest atomic number (usually
hydrogen) has the lowest ranking (fourth).

To the Left or to the Right?

RULE 2 If a decision cant be reached by

ranking the first atoms in the substituent, look
at the second, third, or fourth atoms away from
the chirality center until the first difference is
found.
RULE 3 Multiple-bonded atoms are equivalent
to the same number of single bonded atoms.
Configuration tells you of the rotation of chirals.
The two classifications are S (sinister, Left)
and R (rectus, Right).

To the Left or to the Right?

Optically

As pharmacists, the rotation of compounds are very

important for us. In Physical Pharmacy, potency is
discovered with rotation. Two rotations are seen in a
polarizer; the Levorotatory (left) and the
Dextrorotatory (Right). These two are very important in
drug formulations.
Dextrometorphan, an antitussive, is more potent than
its levorotatory counterpart.
Levothyroxine Sodium, a reformulated thyroid hormone
is more effective in treatment of acute hyperthyroidism.
Esomeprazole is the equal formulation of the levo-dextro
rotatories of the drug. This is non-potent, because dextro
counteracts the effect of levo, the more potent.
Omeprazole, the marketed drug that is potent is more
levorotatory.

Exam Reminders

Web Diagrams

Interconnected components tell of a

story.
This type of exam is given to test the
flexibility of the student. The strategy is
memorization
It asks of

Reagents
Products
Reaction Names

Predicting the X Factor

Predicting missing components of the

web diagram is easy when you come to
know by heart the mechanisms, and
even required reagents or occurring
products.

The main weapon you have here is

memorization. Memorize the Reactions,
Reagents, Products, and yes- even the
catalysts and conditions.

Knowing the Missing:

The Index of Hydrogen Deficiency

Suppose you are given problems about reactions. You are given a
compound A (C8H8) with a strange formula that is almost
impossible. It reacts with a certain reagent then becomes B. The
end point is, they would ask you what are the compounds.

Heres my advice: ASH the problem down

Alkane: Get the Alkane of C8 (Formula: CnH2n+2)

Subtract: Get the difference of the alkane with C8H8
Half: Divide the answer to two, thats the number of your missing H.

And your on your way! If the answer is 1, the structure may be

1 ring or 1 pi bond; if the answer is 2, the structure may be
a triple bond, or a ring with one pi, or two double bonds, or
two rings attached to each other. Have it divisible!
This calculation is called The Index of Hydrogen Deficiency (IHD),
but I prefer it as ASH method.

Some Pointers and Advice

General:

In Organic Chemistry Course, Preliminaries is

composed of the Lec and Lab Exams. This is
only the Lecture.
The prelims is 40% of the total Org Chem
grade.

Passing grade is 75%, however this is still

adjustable, like the quizzes. Aim for Gold! Aim
for Lithium (Scholia Peeps get this :)

Memorize is the best advise.

Tips and Advice

Before the exam, obtain all necessary reviewers and prepare

yourself.
Do not cram.
About 12 to 24 hours before the exam, do not review and try
to relax. Just make quick browsing on your notes. This prevents
you from forgetting some of the most important principles.
It is useful to memorize values.
Make sure you have your permit (if issued), and your
writing aids. If calculators and other tables are allowed, bring
them. Prepare them the night before.
On the exam day, be at the venue about 30 minutes before
the exam. This will relax you, and give you time for some
last minute browsing of notes.
Best advice: Dedicate this fight to the Lord!

Make it Shine!

Study hard! Grades are the reflection of our

hardwork, but it doesnt determine who we are to be.

I apologize for any mistake; in grammar, spelling,

concept, and interpretation contained in this tutorial
presentation.
Presentation Based on: Fundamentals of Organic
Chemistry 7th International Edition (McMurry,
2011)
Photos are taken from the same book and the world
wide web.

I CAN DO ALL THIS

THROUGH HIM WHO
GIVES ME
STRENGTH.
- APOSTLE PAUL,
PHILIPPIANS 4:13
Thanks for Listening! RGO Paragas 2012