84.
204 :
Introduction to Organic and Polymer
Chemistry
Overview of Organic Chemistry
Basic understanding of different categories of
organic compounds like alkanes, alkenes,
alkynes, aromatic compounds, organic
alcohols, ethers, epoxides, aldehydes and
ketones, carboxylic acids and amine
compounds.
Different types of Organic reactions like
substitution,elimination and some typical
polymerization reactions.
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Organic Chemistry
Organic chemistry: Branch of Chemistry in which we study the compounds
of Carbon and Hydrogen and a few other elements like O,N,S,P &
Halogens.
Over 10 million organic compounds have been identified.
About 1000 new ones are discovered or synthesized and identified each day!
What is unique about Carbon??
Catenation
C is a small atom
It forms single, double, and triple bonds.
It has 4 valence electrons.
It is intermediate in electronegativity (2.5).
It forms strong bonds with C, H, O, N, S, the halogens, and some metals.
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Electronic Structure of Atoms
Figure 1.1 Schematic of an
Atom
A small dense nucleus,
diameter 10-14 10-15 m,
which contains positively
charged protons, neutrons,
and most of the mass of the
atom.
Extranuclear space,
diameter 10-10 m, which
contains negatively
charged electrons.
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Electronic Structure of Atoms
Electrons are confined to regions of space
called principle energy levels (shells).
Each shell can hold 2n2 electrons (n = 1, 2, 3,
4......).
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Electronic Structure of Atoms
Shells are divided into subshells called
orbitals, which are designated by the letters
s, p, d,
s (one per shell)
p (set of three per shell 2 and higher)
d (set of five per shell 3 and higher)
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Electronic Structure of Atoms
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Lewis Structures
Gilbert N. Lewis
Valence shell: The outermost electron shell of
an atom.
Valence electrons: Electrons in the valence
shell of an atom. These electrons are used in
forming chemical bonds.
Lewis structure of an atom
The symbol of the atom represents the nucleus and
all inner shell electrons.
Dots represent electrons in the valence shell of the
atom.
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Lewis Structures
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Lewis Model of Bonding
Why do different atoms react??
Atoms react so that each atom acquires the electronic configuration of the
noble gas nearest to it in atomic number.
OCTET RULE
An atom that gains electrons becomes an anion.
An atom that loses electrons becomes a cation.
Formation of CHEMICAL BOND:
Ionic bond: A chemical bond resulting from the electrostatic attraction of an anion
and a cation.
Covalent bond: A chemical bond resulting from two atoms sharing one or more pairs
of electrons.
We classify chemical bonds as ionic, polar covalent, and nonpolar covalent
based on the difference in electronegativity between the bonded atoms.
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Electronegativity
Electronegativity: A measure of the force of
an atom's attraction for the electrons it shares
in a chemical bond with another atom.
Pauling scale
Increases from left to
right within a period.
Increases from bottom
to top in a group.
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Electronegativity
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Electronegativity
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Ionic Bonds
An ionic bond forms by the transfer of
electrons from the valence shell of an atom of
lower electronegativity to the valence shell of
an atom of higher electronegativity.
We show the transfer of a single electron by a
single-headed (barbed) curved arrow.
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Covalent Bonds
A covalent bond forms when electron pairs
are shared between two atoms whose
difference in electronegativity is 1.9 or less.
An example is the formation of a covalent bond
between two hydrogen atoms.
The shared pair of electrons completes the
valence shell of each hydrogen.
Formation of Methane (CH4)
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Polar Covalent Bonds
In a polar covalent bond:
The more electronegative atom has a partial
negative charge, indicated by the symbol .
The less electronegative atom has a partial
positive charge, indicated by the symbol +.
In an electron density model:
Red indicates a region
of high electron density.
Blue indicates a region
of low electron density.
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Drawing Lewis Structures
To draw a Lewis structure:
Determine the number of valence electrons in the
molecule or ion.
Determine the connectivity (arrangement) of atoms.
Connect the atoms by single line between atoms.
Arrange the remaining electrons so that each atom
has a complete valence shell.
Show bonding electrons as single lines.
Show nonbonding electrons as pairs of dots.
Atoms share 1 pair of electrons in a single bond, 2
pairs in a double bond, and 3 pairs in a triple bond.
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Lewis Structures
In neutral molecules containing C, H, N, O,
and halogen
Hydrogen has one bond.
Carbon has 4 bonds and no unshared electrons.
Nitrogen has 3 bonds and 1 unshared pair of
electrons.
Oxygen has 2 bonds and 2 unshared pairs of
electrons.
Halogen has 1 bond and 3 unshared pairs of
electrons.
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Lewis Structures
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Polar and Nonpolar Molecules
A molecule is polar if:
It has polar bonds and
The vector sum of its bonds dipoles is zero (that
is, the bond dipoles cancel each other).
Carbon dioxide has two polar covalent bonds and
because of its geometry, is a nonpolar molecule.
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Polar and Nonpolar Molecules
A water molecule has two polar bonds and,
because its geometry, is a polar molecule.
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Polar and Nonpolar Molecules
An ammonia molecule has three polar
covalent bonds, and because of its geometry,
is a polar molecule.
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Polar and Nonpolar Molecules
Chloromethane and formaldehyde are polar
molecules.
Acetylene is a nonpolar molecule.
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Resonance
A way to describe
molecules and ions for
which no single Lewis
structure provides a truly
accurate representation.
Here are three Lewis
structures for the
carbonate ion:
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Resonance
Linus Pauling - 1930s
Many molecules and ions are best described by
writing two or more Lewis structures.
Individual Lewis structures are called
contributing structures.
Connect individual contributing structures by a
double-headed (resonance) arrow.
The molecule or ion is a hybrid of the various
contributing structures.
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Resonance
Figure 1.12 The carbonate ion as a hybrid of
three equivalent contributing structures.
Curved arrows show the redistribution of
valence electrons between one contributing
structure and the next.
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Resonance
Curved arrow: A symbol used to show the
redistribution of valence electrons.
In using curved arrows, there are only two
allowed types of electron redistribution:
from a bond to an adjacent atom.
from an atom to an adjacent bond.
Electron pushing by the use of curved arrows
is a survival skill in organic chemistry.
learn it well!
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Shapes of Atomic Orbitals
All s orbitals have the shape of a sphere, with
its center at the nucleus.
Of the s orbitals, a 1s orbital is the smallest, a 2s
orbital is larger, and a 3s orbital is larger still.
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Shapes of Atomic Orbitals
A p orbital consists of two lobes arranged in a
straight line with the center at the nucleus.
p orbitals come in sets of three: 2px, 2py, and 2pz.
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Orbital Overlap Model of Bonding
A covalent bond forms when a portion of an
atomic orbital of one atom overlaps a portion
of an atomic orbital of another atom.
In forming the covalent bond in HH, for
example, there is overlap of the 1s orbitals of
each hydrogen.
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Hybrid Orbitals
Hybridization of atomic orbitals.
2nd row elements use sp3, sp2, and sp hybrid
orbitals for bonding.
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Hybrid Orbitals
We study three types of hybrid atomic orbitals:
sp3 (one s orbital + three p orbitals give four sp3 hybrid
orbitals).
sp2 (one s orbital + two p orbitals give three sp2 hybrid
orbitals).
sp (one s orbital + one p orbital give two sp hybid
orbitals).
Overlap of hybrid orbitals can form two types of
bonds, depending on the geometry of the overlap:
bonds are formed by direct overlap.
bonds are formed by parallel overlap.
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sp3 Hybrid Orbitals
Each sp3 hybrid orbital has two lobes of unequal
size.
The four sp3 hybrid orbitals are directed toward the
corners of a regular tetrahedron at angles of
109.5.
Figure 1.16 sp3 hybrid orbitals.
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sp3 Hybrid Orbitals
Figure 1.17 Orbital overlap picture of methane,
ammonia, and water.
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sp2 Hybrid Orbitals
A single sp2 hybrid orbital has two lobes of
unequal size.
The three sp2 hybrid orbitals are directed toward
the corners of an equilateral triangle at angles of
120.
The unhybridized 2p orbital is perpendicular to the
plane of the three sp2 hybrid orbitals.
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sp2 Hybrid Orbitals
Figure 1.19 Covalent bonding in ethylene.
Ethylene is a planar molecule.
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sp2 Hybrid Orbitals
Figure 1.20 A carbon-oxygen double bond consists
of one sigma () bond and one pi () bond.
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sp Hybrid Orbitals
A single sp hybrid orbital has two lobes of unequal
size.
The two sp hybrid orbitals lie in a line at an angle of 180.
The two unhybridized 2p orbitals are perpendicular to each
other and to the line through the two sp hybrid orbitals.
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sp Hybrid Orbitals
Figure 1.22 Covalent bonding in acetylene. A
carbon-carbon triple bond consists of one sigma
() bond and two pi () bonds.
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Hybrid Orbitals
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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
reasons, they are:
The units by which we divide organic compounds
into classes.
The sites of characteristic chemical reactions.
The basis for naming organic compounds.
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Functional Groups
Alcohol: A compound that contains an OH
(hydroxyl group) bonded to a tetrahedral
carbon atom.
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Functional Groups
Amine: A compound that contains an amino
groupa nitrogen atom bonded to one, two,
or three carbon atoms.
Amines are classified as 1, 2, and 3 according
to the number of carbon atoms bonded directly to
the nitrogen atom.
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Functional Groups
Carbonyl group (C=O) of aldehydes and
ketones.
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Functional Groups
Carboxyl group of carboxylic acids.
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