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Uday Maitra, Dept of Organic ChemistryIndian Institute of Science, Bangaloremaitrau@gmail.com/080-2360-1968My coordinates: 13.0165, 77.5686

NCCT-2014HBCSE, Mumbai13th December 2014

“I used to experiment withChloroform as I wanted to getinto the subconscious mind. Itis a highly powerful state ofmind 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

•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?

Questions asked to students who finished high school in 2014

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

Representative response to four important questions

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

“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.”

The Nobel Prize in Physics 1944 was awarded to Isidor Isaac Rabi "for his resonance method for recording the magnetic properties of atomic nuclei".

1st SemesterStructure, bonding, organic chemistry basics

2nd SemesterStereochemistry and Conformation

3rd SemesterSubstitution at sp2 carbon (carbonyl system)Nucleophilic and Electrophilic aromatic substitutionRadical substitutionAddition reaction

4th semesterSpectroscopy: NMR, IR, UV and MSAddition to C=O, Carbonyl Reduction:Elimination reaction: Acyclic and cyclic system, Rearrangements

5th SemesterOrganometallic ChemistryNitrogen compounds: amines TransformationsEnolate chemistry; Synthetic StrategyAsymmetric synthesisCarbocycles and Heterocycles: synthesis and reactionsGreen Chemistry

6th SemesterUnit I:Pericyclic Reactions Advanced spectroscopy Polymers and nanomaterials

Unit II: BiomoleculesCarbohydrates Amino acids and peptides Proteins and Nucleic acids

Undergraduate – organic chemistry courses

(Why lipids are excluded???)

1st SemesterStereochemistry, Pericyclic reactions, spectroscopy

2nd SemesterSynthetic methodology, heterocyclic chemistry, natural products

3rd SemesterOrganic photochemistry and radical reactions

4th SemesterOrganotransition metal chemistry, Asymmetric synthesis, synthesis of complex organic molecules, natural products

Organic specializationHeterocyclic chemistry, medicinal chemistry, stereochemistry of polycylic compounds, bioorganic chemistry

Postgraduate – organic chemistry courses

Physical organic chemistry???

Links for Chemistshttp://www.liv.ac.uk/chemistry/links/link.html

Organic Chemistry Division, ACShttp://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 Tablehttp://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

…Chemistry Education Links

Demonstration Lab at Madison http://www.chem.wisc.edu/deptfiles/genchem/demonstrations/Default.htm

Delights of Chemistryhttp://www.chem.leeds.ac.uk/delights/

Demonstrations and Experiments

Lab experiments

http://www.oc-praktikum.de/nop/en-experiment-3021-overview

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

Free Chemistry Software Links

CH3-CH2-CH2-CH2BrPrimary bromide

CH3-CH2-CH-CH3

-Br

Secondary bromide(CH3)3C-Br

Tertiary bromide

Which one reacts fastest in an SN1 reaction?

R-Br + R’-OH = R-OR’

(CH3)3C-BrTertiary bromide

(CH3)3C-ClTertiary chloride

Which one is a better leaving group, Cl or Br?

A simple demo on reactions

R-Br + R’-OH = R-OR’ + H-Br

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)

Some more resources…

Journal of Chemical Education

Chemistry Comes Alive!

The ‘feather touch’ experiment

Optical rotation

Burning of magnesium in CO2

Water expands on freezing

The beating mercury heart

Visualizing normal modes

GC Instrument simulator

Samples from J. Chem. Educ.Advanced Chemistry Software Collections CD

• No routine home asssignments

• Ask the students to submit a question and its probable answer(must be backed up with an appropriate reference)

• Enjoyable: read books, research papers, and most importantly, think!

• Every student comes up with a different question

A few interesting thoughts...

(question and answer cannot be from any textbook, question bank, or from any school/college or competitive examination)

Ask the students to come up with a question from a structure, plot, or reaction sequence (relevant to the course)

MeBr

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.

A few interesting thoughts...

6. Evaluate if the answers written in italics are correct or not. Givemarks! In case the answer is incorrect, give the correct answer in twosentences.

(a) Solvolysis of compound 1 (t-Bu vs. t-Bu-d9) gives a steric isotope effect(kH/kD ) of 1.1. What would you guess to be the KIE for the solvolysis of

compound 2? Give a brief explanation. [2 +2 = 4]

The observed KIE with compound 2 will be lessthan 1.11.

This is because the C-H bond is longer than the C-D bond and thus less strain isrelieved in compound 2.

R

O

O

NO2

Rt-Bu

1: R = H2: R = CH3

An example

• Stereochemistry and Conformation

• Revisiting Nucleophilic Substitutions

• Kinetics and Reaction Mechanism

• Primary Kinetic Isotope Effect

• Secondary Kinetic Isotope Effect

• Enzyme-inhibitors as Drugs

• Unusual Molecules

http://orgchem.iisc.ernet.in/faculty/um/teaching.html

A few lectures from my website (need to be updated)

maitrau@gmail.com

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