ANDHRA LOYOLA COLLEGE (AUTONOMOUS): VIJAYAWADA-8

B.Sc Chemistry SYLLABUS UNDER CBCS

[2020-21 Batch onwards]
II B.Sc, Semester-4
Course IV (Organic & Spectroscopy of Organic compounds)
4h / w 60 Hrs/Sem No. of Credits-4
Course outcomes: At the end of the course, the student will be able to;
1. Understand nitrogen containing functional groups with respect to their reactivity
2. Comprehend the chemistry of amino acids and Proteins
3. Gain knowledge about the structural elucidation of various mono and disaccharides.
4. Understand and analyse the spectra of organic molecules
5. Comprehend the synthesis and reactivity of various Heterocyclic compounds

Unit I 12 Hrs
(Nitrogen containing functional groups)

Part A
(1 Essay + 1 Short)
Nitro alkanes: Preparation of nitroalkanes, Tautomerism in nitroalkanes, Reactivity – with
HNO2, Nef reaction and Mannich reaction. Amines: Chirality in amines (pyramidal inversion),
preparations– Gabriel synthesis and Hoffman’s bromamide reaction (with mechanisms),
reduction of amides and Schmidt reaction. Primary, secondary and tertiary amines with nitrous
acid, separation of amines by Heinsberg’s method.

Part B
(1 Essay + 1 Short)

Carbylamine reaction, Hoffmann and Cope eliminations. Aromatic amines-Aniline:

preparation and properties - alkylation, acylation, bromination, Nitration and oxidation of
Aniline. Diazonium Salts: preparation and its synthetic applications in the preparation of
arenes, haloarenes, phenols, cyano and nitro compounds. Coupling reactions of diazonium salts
in the synthesis of dyes.
Unit II 12 Hrs
(Amino acids & Heterocyclic compounds)
Part A
(1 Essay + 1 Short)
Amino acids–Definition and classification of Amino acids, Methods of synthesis: synthesis
from halogenated carboxylic acid, Gabriel Phthalimide and Strecker’s synthesis. Physical
properties: Zwitter ion structure and isoelectric point. Chemical reactions – formation of
lactams from gamma and delta amino acids, peptide bond, nomenclature and synthesis of
dipeptides. Determination of primary structure of peptides by Edmandegradation (N-terminal)
and C–terminal (thiohydantoin and with carboxypeptidase enzyme).
 Part B
(1 Essay + 1 Short)
Heterocyclic compounds–Introduction, Synthesis of Pyrrole, Furan and Thiophene by Paul-
Knorr method, resonance and aromaticity in them. Properties: electrophilic substitution at 2 or
5 position, Pyrrole-Acidic character of pyrrole, Halogenation, Nitration and Riemer-Tieman
reaction, Diels Alder reaction in furan and reduction of thiophene with Raney Nickel. Pyridine–
Synthesis, aromaticity and its basic nature comparison with pyrrole- properties - Chichibabin’s
reaction.

Unit III 12 Hrs

(Carbohydrates)
Part A
(1 Essay + 1 Short)
Carbohydrates–Definition and classification of carbohydrates, Mono saccharides: Constitution
(structure elucidation) of Glucose and Fructose, epimers and anomers, mutarotation,
determination of ring size of glucose and fructose, Haworth projections and conformational
structures.
Part B
(1 Essay + 1 Short)
Interconversions of aldoses and ketoses, Killian-Fischer synthesis and Ruff degradation;
Disaccharides–treatment of maltose, lactose and sucrose with respect to hydrolysis, reducing
nature and structures, poly saccharides – starch and cellulose.

Unit IV 12 Hrs
(Molecular, UV-Visible and IR Spectroscopy)
Part A
(1 Essay + 1 Short)
Molecular Spectroscopy: Interaction of electromagnetic radiation with molecules types of
spectra, Rotational spectroscopy–Selection rules, determination of bond lengths of diatomic
molecules, isotopic substitution. Vibrational spectroscopy–Classical equation of vibration,
computation of force constant, Harmonic oscillator, Morse potential curve, vibrational degrees
of freedom for polyatomic molecules, selection rules for vibrationaltransitions, fundamental
frequencies, overtones and combination bands.

Part B
(1 Essay + 1 Short)
UV-Visible: Selection rules, electronic transitions in organic molecules with examples,
concept of chromophore and auxochrome, effect of conjugation on λmax. Woodward rules for
calculating λmax of conjugated dienes (including extended conjugation, ring residues,
exocyclic). IR-spectroscopy–Principle of Infrared spectroscopy, types of vibrations in organic
molecules, fingerprint region. IR spectra of alcohols (inter and intramolecular hydrogen
bonding), aldehydes, ketones, carboxylic acids and amines.
 Unit V 12 Hrs
(H-NMR and Mass Spectroscopy)
Part A
(1 Essay + 1 Short)
Proton magnetic resonance spectroscopy (1H-NMR)–Principle of nuclear magnetic
resonance – shielding and de-shielding - equivalent and non-equivalent protons, Chemical shift
and splitting of signals – spin-spin coupling, application of NMR in distinguishing the isomers
of Butanol, Butanaldehyde, Butanoic acid and Acetophenone.

Part B
(1 Essay + 1 Short)
Mass spectrometry–Principle of mass spectrometry, molecular ion and fragment ions,
isotopic peaks and their importance in the determination of nature of hetero atoms in the
molecule, Mass spectral fragmentation in alcohols (Butanol-1), aldehydes (Butanaldehyde),
ketones (Acetophenone), carboxylic acids (Butanoic acid).

Reference books
1. Morrison, R. T. & Boyd, R. N. Organic Chemistry, Dorling Kindersley (India) Pvt. Ltd.
(Pearson Education).
2. Finar, I. L. Organic Chemistry (Volume 1), Dorling Kindersley (India) Pvt. Ltd. (Pearson
Education).
3. Finar, I. L. Organic Chemistry (Volume 2), Dorling Kindersley (India) Pvt. Ltd. (Pearson
Education)
4. Graham Solomons, T.W. Organic Chemistry, John Wiley & Sons, Inc
5. Spectroscopy of organic compounds by William Kemp
6. Spectroscopy by Pavia
7. Organic Spectroscopy by J. R. Dyer 8. Elementary organic spectroscopy by Y.R. Sharma
9. Spectroscopy of organic compounds by P.S.Kalsi
10. Spectrometric Identification of Organic Compounds by Robert M Silverstein, Francis X
Webster
 From 2021-22
ANDHRA LOYOLA COLLEGE (AUTONOMOUS):: VIJAYAWADA-8
B.Sc - II Year Chemistry, IV Semester Paper IV
Model Paper – Semester End Examinations
(Organic and Spectroscopy of organic compounds)
Time: 3 Hrs Max. Marks: 100
Section - I
I. Answer all the questions. Each carry 16 marks. 5 x 16 = 80 Marks
01. a. Give the mechanism of Hoffmann bromamide reaction?
b. Explain the separation of mixture of amines by Heinsberg’s method?
OR
c. Give the preparation of Benzene diazonium chloride?
d. Give the synthetic applications of benzene diazonium chloride in the preparation of
the following?
i. Fluoro benzene ii. Iodo benzene iii. Phenol
iv. Cyano benzene v. Benzene
e. Explain coupling reaction?
02. a. How do you prepare amino acids by Gabriel phthalimide and Strecker’s synthesis?
b. Write notes on Zwitter ion structure and Iso electric point?
OR
d. Give the preparation of Pyrrole by Paul-Knorr synthesis?
e. Draw the resonance structures in Pyrrole?
f. Pyrrole undergoes electrophilic substitution reactions at 2nd or 5th positions. Why?
03. a. Give the evidences for the open chain structure of Glucose?
b. Give the objections to the open chain structure of Glucose?
c. How do you determine the ring size of Glucose?
OR
d. How the following conversions are affected?
i. Arabinose to Glucose ii. Glucose to Arabinose
e. Draw the structures of Sucrose and Maltose? Give products formed when they
are hydrolyzed? Comment on their reducing nature?
04. a. Give the selection rules for rotational and vibrational spectroscopy?
b. Explain the effect of isotope on the rotational spacing?
c. Calculate the number of vibrational modes in Water and CO2 molecules?
OR
d. Discuss various types of modes of vibrations in organic molecules?
e. Discuss various types of electronic transition possible in organic molecules?
05. a. Give the principle of NMR spectroscopy?
b. Write a note on Chemical shift and Spin-Spin coupling?
OR
d. Give the significance isotopic peaks in Mass spectroscopy?
e. Discuss the fragmentation pattern in Butanaldehyde and Acetophenone?
 Section - II
II. Answer any FIVE questions. Each carry 4 marks. 5 x 4 = 20 Marks
01. Explain Nef reaction?
02. Explain Carbylamine reaction?
03. Explain the classification of amino acids?
04. Explain Chichibabin’s reaction?
05. Write notes on mutarotation?
06. Write a brief note on polysaccharides?
07. Write a note on Finger print region?
08. Distinguish between butanol-1 and butanol-2 by NMR spectroscopy?
09. How do you determine the bond length by rotational spectroscopy?
10. Explain McLafferty rearrangement in Butanoic acid?

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