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Syllabus and Introduction

PHYSICAL ORGANIC CHEMISTRY


(MKS 3401, Compulsory, 2 Credits)

Tutik Dwi Wahyuningsih, Chairil Anwar


Team Teaching Organic Laboratory
Department of Chemistry – UGM

August 2021
RPKPS
(Planning of Learning Activities programs)

SHORT DESCRIPTION

Physical organic chemistry course is a compulsory subject for chemistry


students with 2 credits point. The scope of learning about the
relationship of structure, properties and reactivity; equilibrium, rate and
reaction mechanism; thermodynamic principles and kinetics of organic
reactions; reactive properties and intermediates; pericyclic reactions;
supramolecular concepts and discussion of molecular recognition.
Course Learning Outcomes (CPL-4)
(Capaian Pembelajaran Lulusan yang dibebankan pada MK/CPMK)

Mastering broad and fundamental chemical knowledge in the basic fields


of chemical disciplines (organic, inorganic, analytical, physical and
biochemical chemistry) which includes structure, properties,
functions, changes, energy and dynamics, identification, separation,
characterization, transformation, and synthesis of materials
micromolecular chemistry and its applications.
Course Learning achievement (CPMK)

CPMK1 Analyze the relationship between structure, properties and reactivity


CPMK2 Apply the concept of acid-base properties of organic compounds
CPMK3 Studying the equilibrium, rate, and reaction mechanism
CPMK4 Relate the principles of thermodynamics and the kinetics of organic
chemical reactions
CPMK5 Examine the properties of various reactive intermediates
CPMK6 Studying the pericyclic reaction
CPMK7 Examine the concept of supramolecular chemistry
CPMK8 Applying molecular recognition
Syllabus
TOPICS SUB TOPICS
SUBSTITUEN EFFECTS IN 1. Induction Effect
ORGANIC REACTION 2. Resonance Effect
3. Hyperconjugation Effect
4. Steric Effect
5. Solvation Effect
ACID-BASE CHEMISTRY 1. Bronstead acid-base
2. Aqueous solution
3. Non-aqueous solution
KINETIC AND 1. Energy, enthalpy and entropy
THERMODYNAMIC 2. Energy profile of a reaction
EXPERIMENTS 3. Identify the transition state
4. Hammond's Postulate
5. Functions of catalysts in organic reactions
6. Kinetic vs Thermodynamic Control
Syllabus
TOPICS SUB TOPICS
KINETICS AND 1. Kinetic experiments for simple mechanisms
THERMODYNAMIC 2. Study of intermediates, spectroscopy, trapping for reaction mechanisms
EXPERIMENTS 3. Isotope labeling for reaction mechanisms
4. Primary kinetic isotope effects for the reaction mechanism
5. Hammet-LFER Equation
6. Substituent constant and reaction constant
7. sx- and sx+ (Through conjugation)
8. QSAR and computational chemistry methods
INTERMEDIATES Structure, Stability, Formation, and reaction of
1. Carbocation
2. Radical
3. Carbanion
4. Carbene
5. Tetrahedral Intermediates
6. Prediction of intermediates and transition states based on computational
chemistry
Syllabus
TOPICS SUB TOPICS
PERICYCLIC REACTION 1. Frontier orbital symmetry (Homo-Lumo)
2. Cycloaddition reaction
3. Electrocyclic reaction
4. Sigmatropic Arrangement Reaction
SUPRAMOLECULAR 1. Non-covalent/intermolecular interactions
CHEMISTRY 2. Host-guest chemistry
3. Molecular anchoring
4. Design drug compounds based on molecular anchorage
MOLECULAR RECOGNITION 1. Molecular recognition
2. Self Assembly (protein, polymer)
3. Spherical Recognition (ether crown, calcareous)
Substituen Effects in Organic Reaction
Substituen Effects in Organic Reaction
Acid-Base Chemistry
Equilibrium, Rate, and Mechanism
Kinetic and Thermodynamic Experiments

makin panjang kurang stabil


Intermediate

ada tempatnya
dan ikatan tunggal
Pericyclic Reaction
e transition state of the molecule has a cyclic geometry, the reaction progresses in a concerted fashion, and
the bond orbitals involved in the reaction overlap in a continuous cycle at the transition state

syrata produk hasil siklis melalui paduan, dimungkinkan


melaluia overlapping dan memiliki stereokim yang spesifik

ikatan rangkap dua max


Supramolecular Chemistry
Molecular Recognition

host-guest interaction
between crown ethers
and cations is highly
specific, and the size
and charge of the cation
determine the size and
shape of the cavity that
the cation can fit into

Crown ethers can also form


supramolecular assemblies and host-guest
interactions with inorganic acids and organic
like dissolve like amines containing carboxyl groups

non-covalent interactions include weak intermolecular forces,


electrostatic charge, hydrogen bonding, and van der Waals forces
Physical Organic Chemistry:
Study of the underlying principles and rationale of organic reactions

Some Questions :
⚫ How the reaction takes place ?
⚫ How fast the reaction takes place ? (Kinetics)
⚫ How the energy changes affect the rates of chemical reactions
(Thermodynamics)
⚫ Mechanism of the reaction
17

(The event that take place at the molecular level as reactant


become products)
Physical Organic Chemistry:
Study of the underlying principles and rationale of organic reactions

⚫ If the reaction takes place in one step, What kinds of transition


complex appear between reactant and product ?
⚫ If the reaction takes place in more than one step,
⚫What are these steps ?
⚫What kinds of intermediate intervene between reactant and product
⚫ If reaction takes place via intermediate,
⚫Relative stability of intermediate ? 18

⚫How rapidly the competing reactions take place ?


⚫Thermodynamics or kinetics control ?
Textbooks

1. Sundberg R. J., Carey., F.A., 2000, Advanced


Organic Chemistry, Part A: Structure and
Mechanism, 4th Edition, Kluwer/Plenum Press.
2. McMurry, J. E., 2015, Organic Chemistry, 9th Ed,
Cengage Learning, ISBN- 13: 978-1305080485;
ISBN-10 1305080483.
3. Isaacs, N.S.,1974, Reactive Intermediates in
organic chemistry, John Wiley & Sons Ltd.,
London.
4. Bachrach, S.M., 2014, Computational Organic
Chemistry, 2nd-edition, John Wiley & Sons Ltd.,
New Jersey.
5. Sykes, P., 1986, A Guidebook to Mechanism in
Organic Chemistry, 6th Ed., Longman Group
Ltd., London.
Some examples of Physical organic
chemistry topics
Lengthening the chain by one or
two carbons reduces SN2 reactivity
Some examples of Physical organic
chemistry topics Multiple substitution at the position next to the electrophilic
carbon causes a dramatic decrease in reactivity in S N2
substitution reactions.
Some examples of Physical organic
chemistry topics
Some examples of Physical organic
chemistry topics

SN1 reaction
Some examples of Physical organic
chemistry topics
SN1 Reaction Mechanism
Some examples of Physical organic
chemistry topics
Reaction coordinate diagram for the E1 reaction of 2-chloro-2-methylbutane
Some examples of Physical organic
chemistry topics

E1 Elimination from he base attacks the -hydrogen on the same side as


Cyclic Compounds the leaving group

An E1 reaction involves both syn and anti elimination


Some examples of Physical organic
chemistry topics

E1 Elimination from
Cyclic Compounds

Rearrangement
reaction
THANK YOU

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