BSc LIFE SCIENCE NEP-UGCF

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BSc.

Life Sciences
Multidisciplinary

DISCIPLINE SPECIFIC CORE COURSE (DSC-1): Basic Concepts of Organic

CREDIT DISTRIBUTION, ELIGIBILITY AND PRE-REQUISITES OF THE COURSE

Course t itle & Credits Credit distribution of the course Eligibility Pre-requisite
Code Lecture Tutorial Practical/ criteria of the course
Practice (if any)
Basic Concepts 04 02 - 02 12th Pass NIL
of Organic
Chemistry

Learning Objectives

The Learning Objectives of this course are as follows:


• The course is infused with the recapitulation of fundamentals of organic chemistry
and the introduction of the concept of visualizing the organic molecules in a three-
dimensional space.
• To establish the applications of these concepts, a study of diverse reactions through
mechanisms is included.
• The constitution of the course strongly aids in the paramount learning of the basic
concepts and their applications

Learning outcomes

The Learning Outcomes of this course are as follows:

• Understand and explain the differential behavior of organic compounds based on


fundamental concepts learned.
• Understand the fundamental concepts of stereochemistry.
• Formulate the mechanism of organic reactions by recalling and correlating the
fundamental properties of the reactants involved.
• Learn and identify many organic reactions and their mechanisms including
electrophilic addition, nucleophilic addition, nucleophilic substitution, electrophilic
substitution and rearrangement reactions.

SYLLABUS OF DSC-1

UNIT – I Fundamentals of organic chemistry (6 Hours)


Types of Electronic displacements: Inductive effect, Resonance effect, Hyperconjugation,
Electromeric Effect. Reactive intermediates and their stability: carbocations, free radicals,
carbanions, benzyne, carbenes. Acidity and basicity in organic compounds (comparison of

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carboxylic acids, alcohols, phenols, primary, secondary and tertiary aliphatic amines, aniline
and its derivatives)

UNIT – II Stereochemistry (6 Hours)


Types of projection formulae: Flying Wedge Formula, Newmann, Sawhorse and Fischer
representations and their interconversion.
Stereoisomerism: Concept of chirality (upto two carbon atoms). Configurational isomerism:
geometrical and optical isomerism; enantiomerism, diastereomerism and meso compounds).
Threo and erythro; D and L; Cis-trans nomenclature; CIP Rules: R/ S (for upto 2 chiral
carbon atoms) and E/Z nomenclature (for upto two C=C systems).
Conformational isomerism with respect to ethane, butane and cyclohexane.

UNIT – III Types of Organic Reactions (Including reactions of alkenes, alkyl and aryl
halides, alcohols, aldehydes, ketones) (18 Hours)
Electrophilic addition reactions
Electrophilic addition reaction (with respect to propene, propyne, 3,3-dimethyl-1-butene):
Hydration, Addition of HX in the absence and presence of peroxide, Hydroboration
oxidation, Addition of bromine (with stereochemistry).

Nucleophilic addition reactions


Nucleophilic addition reaction of carbonyl compounds: Addition of HCN, ammonia
derivatives (Hydroxylamine, Hydrazine, Semicarbazide and 2,4-DNP), the addition of
carbanion (Aldol condensation, Claisen Schmidt, Benzoin condensation, Perkin reaction,
reactions involving Grignard reagent).

Elimination and Nucleophilic substitution reactions


Nucleophilic substitution reaction (SN1 and SN2) in alkyl halides (mechanisms with
stereochemical aspect), alcohols (with nucleophiles like ammonia, halides, thiols, ambident
nucleophiles (cyanide and nitrite ion)), ethers (Williamson ether synthesis), Elimination
reaction (E1 & E2), elimination vs substitution (w.r.t. potassium t-butoxide and KOH);
Nucleophilic aromatic substitution in aryl halides-elimination addition reaction w.r.t.
chlorobenzene, including the effect of nitro group (on the ring) on the reaction. relative
reactivity and strength of C-X bond in alkyl, allyl, benzyl, vinyl and aryl halides towards
substitution reactions

Electrophilic substitution reactions


Electrophilic Aromatic substitution with mechanism (benzene)- sulphonation, nitration,
halogenation, Friedel craft acylation :o-, m- and p- directive influence giving examples of
toluene/nitrobenzene/ phenol/ aniline/ chlorobenzene.

Reactive intermediates and Rearrangement Reactions


Free radicals (Birch Reduction); Carbocations (Pinacol-Pinacolone, Wagner-Meerwein,
Rearrangement, and Beckmann rearrangement); Carbanions (Michael Addition); Carbenes
(Reimer-Tiemann).

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Practical component (60 Hours)

1. Purification of an organic compound by crystallization (from water and alcohol) and


distillation, Criteria of purity: Determination of M.P.
2. Determination of boiling point of liquid compounds. (Boiling point lower than and more
than 100 °C by distillation and capillary method)
3. Detection of extra element
4. Preparations: (Mechanism of various reactions involved to be discussed).

a. Bromination of phenol/aniline.
b. 2,4-Dinitrophenylhydrazone of aldehydes and ketones
c. Semicarbazone of aldehydes/ ketones
d. Aldol condensation reaction using green method.
e. Bromination of Stilbene.
f. Acetanilide to p-Bromoacetanilide.

The above derivatives should be prepared using 0.5-1g of the organic compound. The solid
samples must be collected and may be used for recrystallization and melting point.

Essential/recommended readings
Theory:
1. Sykes, P.(2003), A Guide B ook t o Mech anism i n O rganic C hemistry, 6th Edition
Pearson Education.
2. Eliel, E. L. (2001), Stereochemistry of Carbon Compounds, Tata McGraw Hill.
3. Morrison, R. N.; Boyd, R. N., Bhattacharjee, S.K. (2010), Organic C hemistry, 7th
Edition, Pearson Education.
Practical:
1. Furniss, B.S.; Hannaford, A.J.; Smith, P.W.G.; Tatchell, A.R. (2012), Vogel's
Textbook of Practical Organic Chemistry, Pearson.
2. Mann, F.G.; Saunders, B.C. (2009), Practical O rganic C hemistry, Pearson
Education.
3. Dhingra, S; Ahluwalia V.K., (2017), Advanced Experimental Organic Chemistry,
Manakin Press.

Suggestive readings

Theory:
1. Bahl, A; Bahl, B. S. (2019), Advanced Organic Chemistry, 22nd Edition, S. Chand.

Practical:
1. Pasricha, S., Chaudhary, A. (2021), Practical O rganic C hemistry: Volume I , I K
International Publishing House Pvt. Ltd., New Delhi.

Note: Examination s cheme a nd m ode s hall be a s pr escribed by t he E xamination


Branch, University of Delhi, from time to time.

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