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ORGANIC CHEMISTRY!
Created by Gab Paragas for
University of Santo Tomas
SCHOLIA TUTORIAL CLUB
(Monthlies 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 IS CARBON?
WHAT IS CARBON?
WHAT IS CARBON?
WHAT IS CARBON?
POINTERS FOR
ORGANIC CHEMISTRY LECTURE MONTHLIES
Introduction to Organic Chemistry:
Understanding the Nature of Organic
Compounds
Structure and Bonding: Acids and Bases
Polarity
Acidity
and Alkalinity
Functional Groups
Structural Effects
Isomerism, and Basic Interpretations of
Structures
MIND MAP
Organic
IntroChemistry
Acid-Base
to CarbonMonthlies
Chemistry
INTRODUCTION TO ORGANIC
CHEMISTRY:
UNDERSTANDING THE NATURE
OF ORGANIC COMPOUNDS
ORGANIC CHEMISTRY VS
INORGANIC CHEMISTRY
Organic Chemistry
Inorganic Chemistry
However,
FUNCTIONAL GROUPS
FUNCTIONAL GROUPS:
C-C MULTIPLE BONDS
Alkanes: most basic bonding of carbon to
another carbon. Single bonds (sigma bonds/ )
connect these carbons, and mostly hydrogen
atoms take the place of empty spaces. H3C-CH3
Alkenes: double bond between carbons (one
sigma, one pi bond/ ). H2C=CH2
Alkynes: triple bond between carbons (one
sigma, two pi). HC=CH
Prefix
Example
Meth-
Methane
Eth-
Ethene
Prop-
Propene
But-
Butene
Pent-
Pentane
Hex-
Hexyne
Hept-
Heptyne
Oct-
Octane
Non-
Nonane
10
Dec-
Decane
Carbons
CHARACTERISTICS OF COVALENT
BONDS
Bond
Bond
Bond
Bond Angle
Hybridization
Strength
Length
CC
340 kJ/mol
154 pm
109.5
sp-sp
C=C
610 kJ/mol
133 pm
120
sp-sp
C=C
830 kJ/mol
120 pm
180
sp-sp
Covalent bonds are bonds exhibiting equal sharing of electrons
between atoms. These bonds are stable, and they have limitations
to attractions.
CHARACTERISTICS OF COVALENT
BONDS
DEFINING
BOND LENGTH AND BOND
STRENGTH
Bond
Bond
Bond
Bond Angle
Hybridization
Strength
Length
CC
340 kJ/mol
154 pm
109.5
sp-sp
C=C
610 kJ/mol
133 pm
120
sp-sp
C=C
830 kJ/mol
120 pm
180
sp-sp
Bond
Bond
Bond Angle
Hybridization
Strength
Length
CC
340 kJ/mol
154 pm
109.5
sp-sp
C=C
610 kJ/mol
133 pm
120
sp-sp
C=C
830 kJ/mol
120 pm
180
sp-sp
HYBRIDIZATION
sp3-sp3: single bond
between atoms. The sp3
orbital is shaped long
enough, giving you a long
sigma bond.
sp2-sp2: double bond
between atoms.
sp-sp: triple bonds
between atoms
All these hybridization
statuses are depending
on the number of
valence/ outer electrons.
HYBRIDIZATION: CHARACTER
sp3
sp2
sp
s
character
Character
px
py
pz
25%
25%
25%
25%
33%
33%
33%
-------
50%
50%
-------
-------
100%
-------
-------
-------
HYBRIDIZATION
FUNCTIONAL GROUPS:
CYCLICS AND AROMATICS
FUNCTIONAL GROUPS:
CYCLICS AND AROMATICS
Cycloalkane
Benzene/ Aromatic
C6H12
Has no smell.
C6H6
FUNCTIONAL GROUPS:
CARBON SINGLY BONDED TO AN
ELECTRONEGATIVE ATOM
Name
Structure
Name
Example
Ending
Alkyl
Bond
R-X
---------------
CH3Br
Alcohol
R-OH
-ol
CH3CH2OH
Ether
R-O-R
ether
CH3OCH3
Halide
(alkoxy
Carbon
alkane)
Amine
R-NH2
-amine
CH3NH2
Thiol
R-SH
-thiol
CH3SH
Sulfide
R-S-R
sulfide
CH3SCH3
FUNCTIONAL GROUPS:
CARBONYL GROUPS
acid
Anhydrides
Esters
Thioesters
Acid
halides
Amides
Nitriles
Aldehydes
Ketones
POLARITY OF ORGANIC
COMPOUNDS
POLARITY OF ORGANIC
COMPOUNDS
Heres the thing you always have to remember
about polarity: if there is inequality of
electronegativity (ability to attract other atoms to
itself), there is taking poles; a partially positive
(+) pole and a partially negative (-) pole,
thus the name polar. (Also called dipole.)
ELECTRONEGATIVITY
POLARITY OF ORGANIC
COMPOUNDS
+
C-N
(2.5 3.0)
Notice Nitrogens pull to Carbon. The bigger the
electronegativity value, the more negative,
thus, more attracting/ pull.
As the element is more in the right and upper
side of the Periodic Table, the more
electronegative.
POLARITY OF ORGANIC
COMPOUNDS
Take a look at this example:
+
Li - C
(1.0 2.5)
POLARITY OF ORGANIC
COMPOUNDS
POLARITY OF ORGANIC
COMPOUNDS
Take a look:
C Cl
(2.5 3.0)
Polar right? But what if there are four Chlorine
atoms that will bond with Carbon, will it still
be polar?
Cl
Cl C Cl
Cl
Poles are neutralized by opposing pulls. N-Polar.
X
:Y
Non-Polar bonding is called an induced dipole;
because it is not polar, inducing the dipolarity of the
bond. Non Polar bonds are also covalent.
Covalent bonds share e- equally between atoms.
X: Y
Ionic bonding is the total giving up of electrons
from a cation, and an anion takes the valence. This
makes a total positive and total negative character, not
partial (polar).
X+ :Y
Lewis
A Base is a H+ acceptor.
ORGANIC ACIDS
Organic Acids are mostly compounds having the
Carboxylic Acid Group or the C=OOH group.
The longer the chain, the less acidic.
If there is an unusual atom, like a electrophile/ electronrich atom (F, O, N, Cl, Br, I), it is acidic. Take note that
the halogen atoms (except F) are components of strong
acids. They make the compound acidic. The nearer they
are to the C=OOH, the more acidic.
Branching decreases the acidity. Why? Because
branching creates bulkiness, thus the steric effect. If there
is steric effect, the more atoms will be fighting for the
lone electrons of the carboxyl group. Thus less acidic,
more basic.
ORGANIC BASES
Organic Bases are mostly composed of a chain
..
with an amine NH2, the basic component of the organic base.
There is a lone pair above the amine, and the more available it
is, the more basic.
The longer the chain attached to the amine, the less available
the lone pair for bonding.
FORMAL CHARGE:
STRUCTURAL EFFECTS
STRUCTURAL EFFECTS
RESONANCE
(-ELECTRON
DELOCALIZATION)
RESONANCE
(-ELECTRON
DELOCALIZATION)
C-H HYPERCONJUGATION
( - ELECTRON DELOCALIZATION)
INDUCTIVE EFFECT
Electron
Attracting: acidic
Repelling: alkaline
Amines (R NH2)
STERIC EFFECT
It is not ionic.
It is not H-Bonding.
Dipole-Induced
Dipole
Induced Dipole-Induced Dipole
Polar
Non-Polar
H-BONDING
ISOMERISM, AND
BASIC INTERPRETATIONS
OF STRUCTURES
ISOMERS:
COMPOUNDS WHICH ARE NOT
IDENTICAL BUT HAVE THE
SAME CHEMICAL FORMULA.
Isomers
Constitutional
CONSTITUTIONAL ISOMER
STRUCTURES
chain.
Straight: you form a straight chain.
Tip:
CONSTITUTIONAL ISOMER
STRUCTURES
Cycloalkanes
Alcohol Ether
(Alco-Et)
Aldehyde Ketone
(Alco-Ket)
Alkynes Cycloalkenes Alkadienes
Carboxylic Acid Ester
(Carbo-ster)
CONFORMERS
CONFORMERS
STEREOISOMERS
same side
Trans: opposite sides
The rule is that you cut the middle of double bond, then you see if
the compound has the substituents are on the same side or not (ex:
UP - UP). Prioritize the one with a larger atom. no.
STEREOISOMERS
Zusammen:
GENERAL:
In Organic Chemistry Course, Lecture only has a
monthly exam.
The monthlies of the Lecture is equivalent to 20% of the
total Org Chem grade.