Uday Maitra, Dept of Organic Chemistry

Indian Institute of Science, Bangalore NCCT-2014

maitrau@gmail.com/080-2360-1968 HBCSE, Mumbai
1
th
My coordinates: 13.0165, 77.5686 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 5th Semester
Structure, bonding, organic chemistry Organometallic Chemistry
basics Nitrogen compounds: amines
Transformations
2nd Semester Enolate chemistry; Synthetic Strategy
Stereochemistry and Conformation Asymmetric synthesis
Carbocycles and Heterocycles: synthesis
3rd Semester and reactions
Substitution at sp2 carbon (carbonyl Green Chemistry
system)
Nucleophilic and Electrophilic aromatic 6th Semester
substitution Unit I:
Radical substitution Pericyclic Reactions
Addition reaction Advanced spectroscopy
Polymers and nanomaterials
4th semester
Spectroscopy: NMR, IR, UV and MS Unit II: Biomolecules
Addition to C=O, Carbonyl Reduction: Carbohydrates
Elimination reaction: Acyclic and cyclic Amino acids and peptides
system, Rearrangements 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

3rd Semester
Physical organic chemistry???
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-CH2-CH2Br CH3-CH2-CH-CH3 (CH3)3C-Br
Primary bromide Secondary bromide Tertiary bromide

Which one reacts fastest in an SN1 reaction?

R-Br + R’-OH = R-OR’ + H-Br

(CH3)3C-Br (CH3)3C-Cl
Tertiary bromide 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
R of compound 1 (t-Bu vs. t-Bu-d9) gives a steric isotope effect
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
33