Sidho-Kanho-Birsha University
Syllabus & Course Curriculam
Syllabus (CHEMISTRY)
Course Type: MAJ-7
Semester: 5
Course Code: BCEMMAJ07C
Course Title: Organic Chemistry – III
(L-P-Tu): 4-2-0
Credit: 6
Practical/Theory: Combined
Course Objective: COURSE OBJECTIVE OF MAJOR - 7: The syllabus of Major -7 has been designed to provide the
students with in-depth knowledge of addition reactions of alkenes and alkynes, including aromatic electrophilic and
nucleophilic substitution reactions, various react
Learning Outcome: COURSE OUTCOMES OF MAJOR – 7: CO- 7.1 Thorough understanding of addition reactions
involving alkenes and alkynes. CO- 7.2 Detailed study of various aromatic electrophilic and nucleophilic reactions . CO-
7.3 Detailed study of reactions involving carbony
THEORY:
CHEMISTRY OF ALEKENES & ALKYNES: (12 L)
1. Addition to C=C: mechanism (with evidence wherever applicable), reactivity, regioselectivity
(Markownikoff and anti-Markownikoff additions) and stereoselectivity; reactions: hydrogenation,
halogenations, iodolactonisation, hydrohalogenation, hydration, oxymercuration-demercuration,
hydroborationoxidation,epoxidation, syn and anti-hydroxylation, ozonolysis, addition of singlet and
triplet carbenes; electrophilic addition to diene (conjugated dienes and allene); radical addition: HBr
addition; mechanism of allylic and benzylic bromination incompetition with brominations across
C=C; use of NBS; Birch reduction of benzenoid aromatics; interconversion of E - and Z - alkenes;
contra-thermodynamic isomerization of internal alkenes.
2. Addition to C≡C (in comparison to C=C): mechanism, reactivity, regioselectivity (Markownikoff
and anti-Markownikoff addition) and stereoselectivity; reactions: hydrogenation, halogenations,
hydrohalogenation, hydration, oxymercuration-demercuration, hydroboration-oxidation, dissolving
metal reduction of alkynes (Birch); reactions of terminal alkynes by exploring its acidity;
interconversion of terminal and non- terminal alkynes.
AROMATIC REACTIONS: (10 L)
1. Electrophilic aromatic substitution: mechanisms and evidences in favour of it; orientation and
reactivity; reactions: nitration, nitrosation, sulfonation, halogenation,Friedel-Crafts reaction; one-
carbon electrophiles (reactions: chloromethylation, Gatterman-Koch, Gatterman, Houben-Hoesch,
Vilsmeyer-Haack, Reimer-Tiemann, Kolbe-Schmidt); Ipso substitituion.
2. Nucleophilic aromatic substitution: addition-elimination mechanism and evidences in favour of
it; SN1 mechanism; cine substitution (benzyne mechanism), structure of benzyne.
Carbonyl and Related Compounds (30L)
1. Addition to C=O: structure, reactivity and preparation of carbonyl compounds; mechanism (with
evidence), reactivity, equilibrium and kinetic control; Burgi-Dunitz trajectory in nucleophilic
additions; formation of hydrates, cyanohydrins and bisulphite add nucleophilic addition-
elimination reactions with alcohols, thiols and nitrogen- based nucleophiles; reactions: benzoin
condensation, Cannizzaro and Tischenko reactions, reactions with ylides: Wittig and Corey-
Chaykovsky reaction; Rupe rearrangement, oxidations and reductions: Clemmensen, Wolff-
Kishner,LiAlH4, NaBH4, MPV, Oppenauer, Bouveault-Blanc, acyloin condensation;oxidation of
alcohols with PDC and PCC; periodic acid and lead tetraacetateoxidation of 1,2-diols.
2. Exploitation of acidity of α-H of C=O: formation of enols and enolates; kineticand thermodynamic
enolates; reactions (mechanism with evidence): halogenation ofcarbonyl compounds under acidic
and basic conditions, Hell-Volhard-Zelinsky (H. V.Z.) reaction, nitrosation, SeO2 (Riley) oxidation;
condensations (mechanism withevidence): Aldol, Tollens’, Knoevenagel, Claisen-Schmidt, Claisen
ester includingDieckmann, Stobbe; Mannich reaction, Perkin reaction, Favorskii
rearrangement;alkylation of active methylene compounds; preparation and synthetic applicationsof
diethyl malonate and ethyl acetoacetate; specific enol equivalents (lithiumenolates, enamines, aza-
enolates and silyl enol ethers) in connection with alkylation,acylation and aldol type reaction.
3. Elementary ideas of Green Chemistry: Twelve (12) principles of green chemistry;planning of
green synthesis; common organic reactions and their counterparts:reactions: Aldol, Friedel-Crafts,
Michael, Knoevenagel, Cannizzaro, benzoin condensation and Dieckmann condensation.
4. Nucleophilic addition to α,β-unsaturated carbonyl system: generalprinciple and mechanism (with
evidence); direct and conjugate addition, addition of enolates (Michael reaction), Stetter reaction,
Robinson annulation.
5. Substitution at sp2 carbon (C=O system): mechanism (with evidence): BAC2,AAC2, AAC1, AAL1 (in
connection to acid and ester); acid derivatives: amides, anhydrides & acyl halides (formation and
hydrolysis including comparison).
Organometallics: (8L)
Grignard reagent; Organolithiums; Gilman cuprates: preparation and reactions (mechanism with
evidence); addition of Grignard and organolithium to carbonyl compounds; substitution on -COX;
directed ortho metalation of arenes using organolithiums, conjugate addition by Gilman cuprates;
Corey-House synthesis; abnormal behavior of Grignard reagents; comparison of reactivity among
Grignard, organolithiums and organocopper reagents; Reformatsky reaction; Blaise reaction;
concept of umpolung and base-nucleophile dichotomy in case of organometallic reagents.
READING REFERENCES:
1. Clayden, J., Greeves, N., Warren, S. Organic Chemistry, Second edition, Oxford University Press
2012.
2. Sykes, P. A guidebook to Mechanism in Organic Chemistry, Pearson Education, 2003.
3. Smith, J. G. Organic Chemistry, Tata McGraw-Hill Publishing Company Limited.
4. Carey, F. A., Guiliano, R. M. Organic Chemistry, Eighth edition, McGraw Hill Education, 2012.
5. Loudon, G. M. Organic Chemistry, Fourth edition, Oxford University Press, 2008.
6. Norman, R.O. C., Coxon, J. M. Principles of Organic Synthesis, Third Edition, Nelson Thornes,
2003.
7. Morrison, R. N. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd. (Pearson
Education).
8. Finar, I. L. Organic Chemistry (Volume 1), Pearson Education.
9. Graham Solomons, T.W., Fryhle, C. B. Organic Chemistry, John Wiley & Sons, Inc.
10. March, J. Advanced Organic Chemistry, Fourth edition, Wiley.
11. Jenkins, P. R., Organometallic Reagents in Synthesis, Oxford Chemistry Primer, Oxford
University Press.
12. Ward, R. S., Bifunctional Compounds, Oxford Chemistry Primer, Oxford University Press.
PRACTICALS:
Qualitative Analysis of Single Solid Organic Compounds
1. Detection of special elements (N, S, Cl, Br) by Lassaigne’s test.
2. Solubility and classification (solvents: H2O, 5% HCl, 5% NaOH and 5%NaHCO3).
3. Detection of the following functional groups by systematic chemical tests:
4. Aromatic amino (-NH2), aromaticnitro (-NO2), amido (-CONH2, including imide),phenolic – OH,
carboxylic acid (-COOH), carbonyl (-CHO and >C=O); only one testfor each functional group is to be
reported.
5. Melting point of the given compound
6. Preparation, purification and melting point determination of a crystalline derivative of the given
compound.
7. Identification of the compound through literature survey.
Each student, during laboratory session, is required to carry out qualitative chemical tests for all the
special elements and the functional groups with relevant derivatization in known and unknown (at
least six) organic compounds.
REFERENCES FOR PRACTICALS:
1. Vogel,A. I. Elementary Practical Organic Chemistry, Part 2: Qualitative Organic Analysis, CBS
Publishers and Distributors.
2. University Hand Book of Undergraduate Chemistry Experiments, edited by Mukherjee, G.N.
University of Calcutta, 2003.
3. Mann, F.G. & Saunders, B.C. Practical Organic Chemistry, Pearson Education (2009).
4. Furniss, B.S., Hannaford, A.J., Smith, P.W.G., Tatchell, A.R. Practical Organic Chemistry, 5th
Ed.,Pearson (2012).
5. Clarke, H. T., A Handbook of Organic Analysis (Qualitative and Quantitative), Fourth Edition, CBS
Publishers and Distributors (2007).
Basic Features
Undergraduate degree programmes of either 3 or 4-year duration, with multiple entry and exit points and re-entry options,
with appropriate certifications such as:
UG certificate after completing 1 year (2 semesters with 40 Credits + 1 Summer course of 4 credits) of study,
UG diploma after 2 years (4 semesters with 80 Credits + 1 Summer course of 4 credits) of study,
Bachelor’s degree after a 3-year (6 semesters with 120 credits) programme of study,
4-year bachelor’s degree (Honours) after eight semesters (with 170 Credits) programme of study.
4-year bachelor’s degree (Honours with Research) if the student completes a rigorous research project (of 12
Credits) in their major area(s) of study in the 8th semester.
Note: The eligibility condition of doing the UG degree (Honours with Research) is- minimum75% marks to be obtained in the
first six semesters.
The students can make an exit after securing UG Certificate/ UG Diploma and are allowed to re-enter the degree
programme within three years and complete the degree programme within the stipulated maximum period of seven
years.
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