Uday Maitra, Dept of Organic Chemistry
Indian Institute of Science, Bangalore
maitrau@gmail.com/080-2360-1968
My coordinates: 13.0165, 77.5686
NCCT-2014
HBCSE, Mumbai
1
th
13 December 2014
“I used to experiment with
Chloroform as I wanted to get
into the subconscious mind. It
is a highly powerful state of
mind where you can memorise
quickly.”
Outline
• Chemistry in High school
* brief discussion on an ongoing survey
• Some examples from high school textbooks
• Asking questions
• Organic chemistry curricula in UG and PG levels
• Computers/internet – useful resources, a few examples
• Some interesting thoughts
Organic Chemistry in High School
End of Class 11
• Some basic principles and techniques of Organic Chemistry
• Hydrocarbons
2nd half of Class 12
• Haloalkanes and haloarenes
• Alcohol, phenol and ethers
• Aldehydes, ketones and carboxylic acids
• Amines
• Biomolecules
• Polymers
• Chemistry in everyday life
Questions asked to students who finished high school in 2014
•Your name
• Your high school name and location:
• When did you first study Chemistry as a separate subject?
• Which topics/chapters in Chemistry did you like the most? Why?
• Which topics/chapters in Chemistry did not interest you at all? Why?
• Did you do any laboratory experiments?
• Which experiments did you do? Which one did you like the most?
• Did you do any chemistry experiment (e.g. a project) not connected with your
syllabus? If so, please give some details.
• Did any of your chemistry teachers use an innovative method to teach? If so,
could you briefly describe?
• Do you think Chemistry teaching in schools needs to be improved? If the answer
is yes, could you say in a few lines what differences would have made you more
interested in Chemistry?
Representative response to four important questions
Which topics/chapters in Chemistry did you like the most?
• Organic Chemistry, since no memorization was required once you know the
concepts
• Organic chemistry as it is fun to know how reaction works and making new
compounds using reactions
• States of matter, Chemical bonding and Molecular Structure
• ‘Atomic structure', 'bonding' were and are the subjects which fascinate me
• The atomic structure, Chemical bonding, Electro-chemistry, Coordination
chemistry and Organic mechanisms
• Organic Chemistry part, because I find some logical things here, where I can use
my brain, to propose a mechanism, or to explain why something is happening like
that, & this organic part is much more organized.
• Periodic table properties. It was well organized.
• I like the chemistry in everyday life and the chemistry behind the things
which happen in our surrounding
Which topics/chapters in Chemistry did not interest you at all?
• Thermodynamics, Organic, s, p and d-block elements because I did not
understand the mechanism of organic molecules
• Solid state chemistry
• Thermodynamics, surface chemistry
• 'Electrolytic solutions' and all those normality molarity calculations were boring;
so were the Board’s syllabi on inorganic chemistry.
• Electrochemistry. The flow of electrons was not clearly explained
• Kinetic theory of gas, I don't know why
• The detailed study of the Periodic table
• Chemistry of p-block elements
Did any of your chemistry teachers use an innovative method to
teach?
• Used models to teach organic chemistry and structures
• Yes, he used ball and stick models while teaching stereochemistry
• Yes, one of them, but most of them were monotonous.
• NO. They have taught some remembering techniques like...VIBGYOR
• Yes. one of our teacher showed us many experiments when we were in
class VIII.
Do you think Chemistry teaching in schools needs to be improved?
• More practicals and more reaction mechanisms, may be.
• Yes. Labs are not well equipped. Not funded properly. Scarcity of compounds and
reactants like Nessler reagent
• Inorganic chemistry should be taught conceptually and the syllabus should be
accordingly changed.
• Reaction Mechanisms have to be introduced before one starts reading about
organic chemistry
• Yes, Teachers can use projectors and pictures. No one thinks that remembering hard
reactions are the main part of Chemistry.
• Use some e-technology to show the actual things which we r studying as theory.
using some model, doing experiments from very basic levels
• All the teachers teach organic reactions without reaction mechanism
• More practicals
• Various software, models and Internet should be taken to teach chemical and
crystal structures
• Chemistry needs to be taught in a more interactive manner, and should not solely
test the memory skills of a student. Demonstrations and visually stimulating
experiments related to the concepts being taught can motivate many students to
look at chemistry as a viable career option.
Electrochemical concepts
Give examples of each class
Mention uses in real life
• 9 volt battery
• 2 pencils
• Petridish on an overhead projector
• Water with vinegar
• pH indicator
•Water with common salt
•Starch iodide paper
The power of
The Nobel Prize in Physics 1944 was awarded
to Isidor Isaac Rabi "for his resonance
method for recording the magnetic properties
of atomic nuclei".
“My mother made me a scientist without ever intending to. Every
other Jewish mother in Brooklyn would ask her child after school:
So? Did you learn anything today? But not my mother. “Izzy,” she
would say, “did you ask a good question today?” That difference
— asking good questions — made me become a scientist.”
Undergraduate – organic chemistry courses
1st Semester
Structure, bonding, organic chemistry
basics
2nd Semester
Stereochemistry and Conformation
3rd Semester
Substitution at sp2 carbon (carbonyl
system)
Nucleophilic and Electrophilic aromatic
substitution
Radical substitution
Addition reaction
4th semester
Spectroscopy: NMR, IR, UV and MS
Addition to C=O, Carbonyl Reduction:
Elimination reaction: Acyclic and cyclic
system, Rearrangements
5th Semester
Organometallic Chemistry
Nitrogen compounds: amines
Transformations
Enolate chemistry; Synthetic Strategy
Asymmetric synthesis
Carbocycles and Heterocycles: synthesis
and reactions
Green Chemistry
6th Semester
Unit I:
Pericyclic Reactions
Advanced spectroscopy
Polymers and nanomaterials
Unit II: Biomolecules
Carbohydrates
Amino acids and peptides
Proteins and Nucleic acids
(Why lipids are excluded???)
Postgraduate – organic chemistry courses
1st Semester
Stereochemistry, Pericyclic reactions, spectroscopy
2nd Semester
Synthetic methodology, heterocyclic chemistry, natural products
Physical organic chemistry???
3rd Semester
Organic photochemistry and radical reactions
4th Semester
Organotransition metal chemistry, Asymmetric synthesis, synthesis
of complex organic molecules, natural products
Organic specialization
Heterocyclic chemistry, medicinal chemistry, stereochemistry of
polycylic compounds, bioorganic chemistry
Chemistry Education Links…
Links for Chemists
http://www.liv.ac.uk/chemistry/links/link.html
Organic Chemistry Division, ACS
http://www.organicdivision.org/
Organic Data tables
http://www.chem.wisc.edu/areas/organic/index-chem.htm
Learn Chemistry
http://www.rsc.org/learn-chemistry/
Science is Fun
http://scifun.chem.wisc.edu/
Indian Academy of Sciences (Bangalore)
http://www.ias.ac.in
…Chemistry Education Links
Periodic Table
http://www.meta-synthesis.com/webbook/35_pt/pt.html
Classic Chemistry
https://web.lemoyne.edu/giunta/
Classic Papers
https://web.lemoyne.edu/giunta/papers.html
List of Name reactions (about 145)
http://www.monomerchem.com/display4.html
Demystifying Synthetic Organic Experimental Techniques
http://chem.chem.rochester.edu/~nvd/
Molecule of the Month
http://www.bris.ac.uk/Depts/Chemistry/MOTM/motm.htm
Demonstrations and Experiments
Demonstration Lab at Madison
http://www.chem.wisc.edu/deptfiles/genchem/demonstrations/Default.htm
Delights of Chemistry
http://www.chem.leeds.ac.uk/delights/
Lab experiments
http://www.oc-praktikum.de/nop/en-experiment-3021-overview
Free Chemistry Software Links
http://www.sciencegeek.net/Chemistry/chemware/chemware.shtml
http://www.claessen.net/chemistry/soft_en.html
http://www.internetchemistry.com/chemistry-index.html
http://ww2.chemistrycoach.com/
http://hbell.chem.vt.edu/simulation/hb2/TESTPAGE.htm
A simple demo on reactions
-
Br
CH3-CH2-CH-CH3
Secondary bromide
CH3-CH2-CH2-CH2Br
Primary bromide
(CH3)3C-Br
Tertiary bromide
Which one reacts fastest in an SN1 reaction?
R-Br + R’-OH = R-OR’ + H-Br
(CH3)3C-Br
Tertiary bromide
(CH3)3C-Cl
Tertiary chloride
Which one is a better leaving group, Cl or Br?
Some more resources…
Organic Chemistry (McMurry)
Maxwell distribution (vs. temperature, vs. mass)
Titration of a weak acid, Chromatogram simulation
J. Chemical Education Software
(http://www.jce.divched.org/jce-products)
Journal of Chemical Education
Chemistry Comes Alive!
Water expands on freezing
Optical rotation
Burning of magnesium in CO2
The beating mercury heart
The ‘feather touch’ experiment
Samples from J. Chem. Educ.
Advanced Chemistry Software Collections CD
Visualizing normal modes
GC Instrument simulator
A few interesting thoughts...
• No routine home asssignments
• Ask the students to submit a question and its probable answer
(must be backed up with an appropriate reference)
(question and answer cannot be from any textbook, question
bank, or from any school/college or competitive examination)
• Enjoyable: read books, research papers, and most importantly, think!
• Every student comes up with a different question
A few interesting thoughts...
Ask the students to come up with a question from a structure,
plot, or reaction sequence (relevant to the course)
Br
Me
NH2
NH2
A few interesting thoughts...
Provide a question with answer(s), which may be correct,
partially correct, or completely wrong!
Ask the student to read the question, and evaluate the
answer.
An example
6.
Evaluate if the answers written in italics are correct or not. Give
marks! In case the answer is incorrect, give the correct answer in two
sentences.
(a)
Solvolysis
of compound 1 (t-Bu vs. t-Bu-d9) gives a steric isotope effect
R
t-Bu O
(kR H/kD ) of 1.1. What would you guess to be the KIE for the solvolysis of
O
compound 2? Give a brief explanation.
[2 +
1: R = H
NO2 2 = 4]
2: R = CH3
The observed KIE with compound 2 will be less
than 1.11.
This is because the C-H bond is longer than the C-D bond and thus less strain is
relieved in compound 2.
A few lectures from my website (need to be updated)
http://orgchem.iisc.ernet.in/faculty/um/teaching.html
• Stereochemistry and Conformation
• Revisiting Nucleophilic Substitutions
• Kinetics and Reaction Mechanism
• Primary Kinetic Isotope Effect
• Secondary Kinetic Isotope Effect
• Enzyme-inhibitors as Drugs
• Unusual Molecules
maitrau@gmail.com
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