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ORGCHEM Lec 1-1

The document provides an overview of topics to be covered in an organic chemistry lesson over the course of a week, including: 1) The history of organic chemistry from the vitalism theory to Wohler's synthesis of urea. 2) Atomic structure theories from Dalton to Schrodinger and electron configurations. 3) Chemical bonding theories including valence bond theory and hybridization. 4) Polar and nonpolar covalent bonds and electronegativity. Sample exercises are also provided on predicting acid-base reactions from pKa values and identifying Lewis acids and bases.

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Nathan Ray Alim
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37 views70 pages

ORGCHEM Lec 1-1

The document provides an overview of topics to be covered in an organic chemistry lesson over the course of a week, including: 1) The history of organic chemistry from the vitalism theory to Wohler's synthesis of urea. 2) Atomic structure theories from Dalton to Schrodinger and electron configurations. 3) Chemical bonding theories including valence bond theory and hybridization. 4) Polar and nonpolar covalent bonds and electronegativity. Sample exercises are also provided on predicting acid-base reactions from pKa values and identifying Lewis acids and bases.

Uploaded by

Nathan Ray Alim
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© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Nathan Ray Alim, Ph.D.

LESSON OVERVIEW
• Week 1
– History of Organic Chemistry
– Atomic structure
– Electron configuration
– Chemical bonding theory (Valence Bond Theory,
Hybridization)
– Polar and nonpolar covalent bonds
– Electronegativity
TEXTBOOK:
https://www.dropbox.com/s/117swhykztyqjwf/McMurry%208
E%20Organic%20Chemistry.pdf?dl=0
HISTORY OF ORGANIC CHEMISTRY
• The name organic chemistry came from the word
organism.
• Prior to 1828, all organic compounds had been
obtained from organisms or their remains. The
scientific philosophy back then was that the
synthesis of organic compounds could only be
produced within living matter while inorganic
compounds were synthesized from non-living
matter.
• A theory known as "Vitalism" stated that a "vital
force" from living organisms was necessary to make
an organic compound.
• In 1828, a German chemist Friedrich Wöhler (1800-
1882) amazed the science community by using the
inorganic compound ammonium cyanate, NH4OCN
to synthesize urea, H2NCONH2, an organic substance
found in the urine of many animals. This led to the
disappearance of the "Vitalism" theory.
MODERN ORGANIC CHEMISTRY
ATOMIC THEORY

• SOLID SPHERE MODEL – JOHN DALTON


• PLUM PUDDING MODEL – J. J. THOMSON
• NUCLEAR MODEL – ERNEST RUTHERFORD
• PLANETARY MODEL – NIELS BOHR
• QUANTUM MODEL – ERWIN SHRÖDINGER
ATOMIC STRUCTURE
HISTORY OF ATOMIC THEORY
ATOMIC STRUCTURE
ATOMIC STRUCTURE
ATOMIC STRUCTURE –
Electron Configuration
ATOMIC STRUCTURE – Electron Configuration
CHEMICAL BONDING THEORY

ASSIGNMENT: READ ON THE HISTORY OF THE DEVELOPMENT OF KEKULE AND LEWIS STRUCTURES
CHEMICAL BONDING THEORY
CHEMICAL BONDING THEORY
VALENCE BOND THEORY
• According to valence bond theory, a covalent bond forms
when two atoms approach each other closely and a singly
occupied orbital on one atom overlaps a singly occupied
orbital on the other atom. The electrons are now paired in
the overlapping orbitals and are attracted to the nuclei of
both atoms, thus bond- ing the atoms together. In the H2
molecule, for instance, the H–H bond results from the
overlap of two singly occupied hydrogen 1s orbitals.
VALENCE BOND THEORY
ATOMIC ORBITALS
Hybridizations of C – sp 3

• Hybridization of the s and the three p orbitals (px, py, pz) results to four
sp3 hybridized orbitals.
• This orbital has 25% ‘s’ character, and usually characterized by 109.5°
bond angles.
Hybridizations of C – sp 3

• Hybridization of the s and the three p orbitals (px, py, pz)


results to four sp3 hybridized orbitals.
• This orbital has 25% ‘s’ character, and usually characterized
by 109.5° bond angles.
Hybridizations of C – sp 2

• Hybridization of the s and the two p orbitals results to three


sp2 hybridized orbitals and one p orbital.
• This orbital has 33% ‘s’ character, and usually characterized
by 120° bond angles.
Hybridizations of C – sp

• Hybridization of the s and one p orbital results to one sp


hybridized orbitals, and two unhybrized p orbitals.
• This orbital has 50% ‘s’ character, and usually characterized
by 180° bond angles.
Bond Strengths
Polar Covalent Bonds

• Bond polarity is due to differences in


electronegativity (intrinsic property of an atom
to attract electrons to itself).
Electronegativity Differences

• Bond polarity is due to


differences in
electronegativity
(intrinsic property of an
atom to attract
electrons to itself).

• Electrostatic potential maps also shows poor electron


density in neighboring atoms due to the inductive
effects of the electronegative (Example a).
Dipole Moments
• μ=Qxr
– μ: dipole
moment (D or
3.336 x 10–30 C-
m)
– Q: charge of
the particle
(e.g. electron)
– r: distance
between the
charges (e.g.
internuclear
radii)
Formal Charge

• Formal charges are a sort of formalism and do not


necessarily mean actual ionic charge. They are a device used
for electron ‘tracking’ or ‘bookkeeping’ in a compound.
Molecular Orbital Theory
Molecular Orbital Theory
Drawing Chemical Structures
Drawing Chemical Structures
Drawing Chemical Structures
Resonance

• In actual,
compounds
with
resonance
forms exist as
a resonance
hybrid.
Rules in Writing Resonance Forms
• Rule 1
– Individual resonance forms are imaginary,
not real. The real structure is a composite, or
resonance hybrid of the different forms.
Compounds with different resonance
structures such as acetate and benzene have a
single unchanging structure. Resonance
structures are sheer representations we draw
on paper to describe the movement of
electrons in a molecule.
Rules in Writing Resonance Forms
• Rule 2
– Resonance forms differ only in the placement of
π and non-bonding electrons. Having said that, it
also retains the hybridization of the carbon atom.
Rules in Writing Resonance Forms
• Rule 3
– Different resonance forms of a substance
don’t have to be equivalent.
Rules in Writing Resonance Forms
• Rule 4
– Resonance forms obey normal valency.
Rules in Writing Resonance Forms
• Rule 5
– The resonance hybrid is more stable than any
individual resonance form. Resonance leads
to stability.
Acids and Bases:
The Brønsted-Lowry Definition

• Brønsted acid – Hydrogen ion (H+) donor


• Brønsted base – Hydrogen ion (H+) acceptor
Acids and Bases: The Brønsted-Lowry Definition
Acids–Base Strength
• Measured in pKa, pKa = -log Ka
Sample Exercise
Sample Exercise
Predicting Acid-Base Reactions from pKa values
Sample Exercise
Sample Exercise
Sample Exercise
Sample Exercise
Organic Acids
Organic Acids
Organic Acids
Evans’ pKa Table
Organic Bases
Lewis Acids and Bases

• Lewis Acid
– Electron pair acceptors.
• Lewis Base
– Electron pair donors.
Lewis Acids and the Curved Arrow Formalism
Lewis Acids and Bases
Lewis Acids and Bases
Lewis Acids and Bases
Lewis Acids and Bases
Lewis Acids and Bases
Sample Exercises
Sample Exercises
Sample Exercises

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