Unit 1) General Organic Chemistry

What is organic compound?

Molecules containing carbon, typically bonded to

hydrogen, oxygen, nitrogen, and other elements.

a) Basics l
Organic Chemistry is all about reactions.

¥ Reagents Ð Reactive chemical species that trigger the reaction

by attacking another species.
¥ Substrate Ð The species that is attacked by a reagent in an
organic reaction.

Bond Fission

breakage of existing
chemical bonds and
the formation of new
ones.
Electrophiles Ð They are electron-deficient species
that attack the substrate at a region where the
electron density is high.

Nucleophiles Ð They are electron-rich species that

tend to donate their electrons. generally attack
the reagent at a region where the electron density
is low.

Bond break in two different ways:

Homolytic Fission
Each participating atom leaves with one
unpaired electron. The chemical species that
are created as a result of homolytic fission
are called free radicals. They are highly
Take place in any solvent
reactive (due to their unstable electron
configurations).
Heterolytic Fission
*Do not depend on type of atom
One atom retains both the electrons and the
other retains none. Heterolytic fissions
feature the formation of an ion pair Ð a
positively charged cation and a negatively
charged anion.
Take place in polar solvent *Electronegativity of A and B should be different .

Jo e- leta hai vo Negative Jo e- deta hai vo positive

Water
CH3 Br

CH3 Br
Sunlight
CH3 Br
Classification of Organic compounds based on functional Group
 Reaction Intermediates

Homolytic and heterolytic bond fission forms short lived

species called as reaction Intermediates.
These short lived species are very reactive and are
quickly converted to more stable molecules.

Reactants→ Intermediate (Transition State) → Product

Puri organic
chemistry me
har koi apna
octate pura krne
ke liye tadap rha
hota hai,
Hybridization You can find the
hybridization of an
atom by finding its
steric number: The steric
Can anyone please number = the number of
tell me how to atoms bonded to the atom
calculate the + the number of lone
hybridization? pairs the atom has. If the
steric number is 4, the
atom is s p 3 hybridized.
If the steric number is 3,
the atom is s p 2
hybridized and if it is 2
then sp hybridized
 Hydrogen Bonding
Hydrogen bonds form between molecules when hydrogen is covalently
bonded to small, highlyelectronegative atoms such as:

Oxygen You do a lot of

¥ Example: H20 How can we bonding talking
with your
Fluorine remember
friends on the
¥ Example: HF these? FON.
Nitrogen
¥ Example: NH3

Electronegativity

F, O, N -
Top 3 highest
electronegativity
b)Isomerism
 Conformational Isomers

Potential Energy is inversely proportional to stability

 c)Steps for IUPAC
Naming of a Compound
Step 1: Identify the carbon chain with Step 3: Determine what the prefix
the longest length in our compound. (starting) & suffix (ending) should be.

Step 2: Identify the longest carbon

chain root name.

Step 4: Give the side groups names.

The infixes, like cyclo, spiro,

bicyclo, are added between the
prefix(es) and root word in the
IUPAC name to indicate the nature
of parent chain.
 d)Electron Displacement Effect

Polarisation effect Polarisability effect

(permanent) (temporary)

Inductive Hyperconjugative

Inductomeric Electromeric
Resonence

+I
Inductive Effect
-I
The introduction of an electron-rich or electron-
deficient species to a carbon chain results in the Important Note: The magnitude of the partial charge
decreases down the carbon chain. Its magnitude can be
formation of a permanent dipole. This effect is neglected from the 4th carbon atom in the chain.
called the inductive effect since the dipole is
induced by the difference in the electronegativities
of the atoms in the molecule.

1 It is a permanent effect.
2 It is dependent on distance (its magnitude decreases as the distance between the atoms increases).
3 It is relayed through sigma bonds.

Important Note: electron-donating species decrease the Remember:

stability of carbanions and increase the stability of ¥ -I Groups (electron-withdrawing groups) increase
carbocations due to the +I effect. Electron-withdrawing acidity and decrease the basicity.
species increase the stability of carbanions and decrease the ¥ +I Groups (electron-donating groups) decrease
stability of carbocations due to the -I effect. acidity and increase basicity.
 +R Effect: It occurs when a lone pair of
electrons is released into a molecule.
Resonance effect
The resonance effect involves the delocalization of pi electrons -R Effect: It occurs primarily due to electron-
and lone pairs over molecules. This results in several withdrawing species or species with vacant p or d
hypothetical molecular structures known as resonance orbitals.
structures. It occurs at an intramolecular level and does not
alter the structural arrangement of atoms in the molecule (the
arrangement of electrons can vary).

The stabilization offered by resonance is greatest when an equivalent resonating structure (known as a
resonance hybrid) can be drawn for the molecule.

For O3

For Co3
 Conditions for Resonance

(i Compound must be planar (sp/sp2)

(ii) Compound must be conjugated.

Rules for drawing Resonating Structure

Rule - 1
Each RS of a compound must have a valid structure (octet rule
must be followed except atoms with variable valency)

Rule - 2
Each RS must have same number of unpaired electrons

Rule-3
Each RS must have each atom at its own position and must be
same in all RS. Resonance is a phenomena of delocalization of -
electrons only (no movement of a electrons)

Rule-4
RS having unlike charges on adjacent same atoms is usually
neglected in consideration to contribution to hybrid as they are
highly unstable.

No of Resonating structures?
 +R effect corresponds to mesomeric effect. It is the phenomenon by which
an aromatic ring gets activated at different corners of the ring.(Benzene).
Groups like F, Cl,OH, OR and NH2, NHR, NR2 etc. are found to show +R
effects
Gives e- to ring- lone pairs , negative charge species

-R effect is the phenomenon when a functional group participating in

resonance induces relatively greater positive charge in the first and the
third atom of the ring.
Groups like COOH, CHO, NO2, CN and NO etc show ÐR effect.

Takes e- from ring- positive charge species

Principle 1. Atoms, in general, ÒdonÕt likeÓ charges, so having no charge is better:

Principle 2. The resonance structure with a complete octet is more stable:

Principle 3. The Resonating structures having unlike charges closer and like charges away
are more stable

Principle 4. The Resonating structures having negative charge on more

electronegative & +ve charge on the more electropositive atom is relatively more
stable:
 Hyperconjugation
Carbocations are stabilised by adjacent sigma bonds that donate electrons to vacant p-
orbitals. This effect is a permanent effect and is called hyperconjugation (also called
no-bond resonance). Here, the delocalization of the positive charge increases stability of
compound.
The stability added by hyperconjugation is directly proportional to the total number of
hyper-conjugating structures, which is, in turn, directly proportional to the total number of
alpha hydrogens.
*Do not depend on dist'a''n'ce. Only inductive effect depends on distance

No of hyper conjugating
structure = 1 +no of alpha
hydrogens ,

Negatives charge and free radical

Plus Charge and double bonds

Order of Priority:

Aromaticity> Dancing resonance ( observed in

tricyclopropylmethyl carbocation ) > resonance effect >
hyperconjugation > electromeric effect > inductive effect.

Note: For Halogens Inductive effect is more dominating than resonence

 e)Aromaticity
What is Aromatic compound ?
All cyclic compounds which are unusually stabilised than its
analogous open chain structure.

Q1
What are the four conditions for aromaticity?
It should be in a ring form.
It should be planar or flat. (sp or sp2)
It should be Conjugated.
It must satisfy the 4n + 2 rule. Huckle Rule
n must be positive integer for aromatic compound
 f)Acid base Strength

Acids are proton Bases are proton

donors/ electron accepters/ electron
pair acceptors. pair doners.

Isolated > Resonated > Aromatic

+I effect +R effect directly proportional to Basic strength

-I effect -R effect directly proportional to Acidic strength
Basic strength is vice versa of acidic strength
' More effective position order

P> o> m
In Hydrogen bonding case Otho will be more powerful

Example
g)Common types of organic reactions