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B.S. ORGANIC CHEMISTRY [CHM-302] SYLLABUS
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1. Chemistry Of Hydrocarbons:
A) Alkanes:
Nomenclature, natural occunence and physical properties
Preparation of alkanes: Hydrogenation of alkenes; Reduction of alkyl
halides [Hydrolysis of grignard reagent and reduction by metal and
acid; Reduction by alkali metal hydrides Wurtz reaction; Kolb'e electrolysis.
Reactions of alkanes: Oxidation of alkanes; Combustion, energy of activation and heat of reaction;
Halogenation of alkanes; Mechanism of halogenation; Orientation of halogenation, Free radical reactions,
stability of free radicals, orientation and reactivity of free radicals. Sulfochlorination, Intermediates for
the production of detergents; Nitration; Insertion of methylene group; Pyrolysis: Cracking.
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B) Alkenes:
Nomenclature, natural occurrence and physical properties, Preparations
of alkenes: Partial hydrogenation of alkynes; Dehydration of alcohols
[Pyrolytic dehydration, acid catalysed dehydration]; Dehydrohalogenation
of alkyl halides; Dehalogenation of vicinal dihalides. Reactions of
Alkenes: Electrophilic addition reactions [Addition of hydrogen halides,
halogens, sulfuric acid, water (hydration), hypohaJous acid]. Mechanism
of electrophilic addition reactions and orientation of addition (Markonikov's
rule). Formation and relative stability of carbonium ions. Radical
addition to alkenes [Anti-markonikov addition of hydrogen bromide.
Oxidation of alkynes; Oxidative cleavage of alkenes; Hydroxylation
with OSO4 and KMnO4; Degradation by ozonolysis; Epoxidation by peroxyacids.
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C) Alkynes:
Nomenclature, natural occurrence and physical properties; Preparation
of alkynes: Dehydroha1ogenation of alkyl dihalides; Reactions of Alkynes:
Addition reactions (addition of halogens and hydrogen halide). Oxidative
cleavage of alkynes.
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D) Cycloalkanes (Alicyclic Compounds):
Nomenclature, natural occurrence and physical properties;
Relative stability of small, normal, medium and large sized rings;
Synthesis of three, four, five and six membered rings. Reactions of
cycloalkanes; Ring opening reactions. Ring expansion reactions.
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2. Aromatic Hydrocarbons And Hetrocyclic Compounds :
Nomenclature of simple aromatic systems and five and six
membered heterocyclic rings containing O, N and S. Aromaticity. Preparation
of aromatic compounds. Synthesis of benzene, pyridine and furane.
Preparation of condensed aromatic systems (naphthalene and anthracene).
Reactions of aromatic compounds.
Comparision of reactivity of benzene, aromatic heterocyclic systems
and condensed aromatic systems. E1ectrophilic substitution reactions
of benzene and heterocyclic aromatic compounds (five and six membered)
including nitration, sufonation, ha1ogenation, Friedel-Crafts acylation
and Friedel-Crafts alkylation. Mechanism of electophilic substitution
reactions. Orientation in benzene. Oxidation of alkyl benzene.
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3. ALKYL Halldes:
Nomenclature, classification and physical properties; Preparation
of alkyl halides: From alcohols; Halogenation of certain hydrocarbons;
Addition of HX and X2 to alkenes and alkynes; Hunsdiecker reaction;
Haloform reaction. Reactions of alkyl halides: Nucleophilic substitution
reactions; Mechanism of Nucleophilic substitution reactions. Elimination
reactions; (Zaitsev rule and Hofmann rule). Competition between SN
and elimination reactions; Grignard reagent: Preparation and reactions.
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4. Chemistry Of Hydroxyl Group And Ethers:
Nomenclature, classification and physical properties of alcohols, phenols
and ethers; Preparation of alcohols: Hydroboration-oxidation of alkenes.
Reaction of Grignard reagent with carbonyl compounds. Hydrolysis of
alkyl halides. Reduction of carbonyl compounds, acids and esters. Hydroxylation
of alkenes. Reactions of Alcohols: Acid catalyzed reaction of alcohols
with HX. Oxidation of alcohols. Preparation of phenols: Hydrolysis of
diazonium salts. Alkali fusion of sulfonates. Hydrolysis of aryl halides.
Reactions of phenols: Acidity (salt formation). Ester formation. Electrophilic
substitution reaction (Halogenation, nitration, su1fonation, Friedel-Crafts
alkylation and Friedel-Crafts acylation, nitrosation). Ether formation
(Williamson's synthesis). Preparation of ethers: Reactions of ethers;
Cleavage by acids.
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5. Chemistry Of Carbonyl Compounds:
Comparative study of Structure and reactivity of aldehydes, ketones,
carboxylic acids and their derivatives.
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A) Aldehydes And Ketones:
Nomeoc1ature, natural occurrence and physical properties. Preparation
of aldehydes and ketones; Oxidation of 10 and 20 alcohols; Friedel-Crafts
acylation (for aromatic carbonyl compounds); Hydration of a1kynes;
Glycol cleavage; Ozonolysis of aIkenes. Reactions of aldehydes and
ketones; Nucleophilic Addition Reactions; Hydration and Hemiacetal
Formation; Acetal Formation; Formation of Imines and Related Compounds;
Enamine Formation; Cyanohydrin Formation; Reduction by Complex Metal
Hydrides; Addition of Organometallic Reagents; Reactions at the a-Carbon;
The Aldol Reaction; Dehydration of Aldol Products; Mixed Aldol Condensations.
Other Carbonyl Group Reactions; Reduction (Wolff-Kishner Reduction,
Clemmensen Reduction and Hydrogenolysis of Thioacetals); Oxidation
(Tollens test, Benedict’s test and Fehling’s test); Cannizzarro’s
reaction; Halogenation of ketones.
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B) Carboxylic Acids And Their Derivatives:
Nomenclature, natural occurrence and physical properties. Preparation
of carboxylic acids; Oxidation of primary alcohols; Oxidation of alkylbenzenes;
Carbonation of grignard reagent; Hydrolysis of nitriles. Reactions
of carboxylic acids: Acidity: Salt formation; Conversion into functional
derivatives. Conversion into acid chlorides. Conversion into anhydrides.
Conversion into esters. Conversion into amides.
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6. Chemistry Of Amines:
Nomenclature, classification and physical properties of amines.
Preparation and reactions of amines.
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7. Carbohydrates:
Introduction. Classification Mono, di- and polyosaccharides;
Aldoses and hexoses; Reducing and non-reducing sugars. Structure:
Cyclic forms of monosaccharides; The configuration and important reactions
of glucose.
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Practicals:
Qualitative Organic Analysis:
Identification of compound containing C, H, 0 and N or S
and functional groups [Hydrocarbon, Carboxylic acid, Phenol, Amide,
thioamide, Aldehyde or Kketone]. Preparation of their derivatives.
Quantitative analysis of organic compounds containing COOH group.
Synthesis of organic compounds: phtbalimide and iodoform. Isolation
of compounds from natural products: casein from milk and isolation
of starch from potato.
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Recommended Text:
1. Solomons TWG “Organic chemistry” 5th Ed (1992)
John Wiley & Sons Inc. New York.
2. Morrison RT and Boyd RN “Organic Chemistry” 6th Ed
(1992) Prentice-Hall of India Pvt. Ltd. New Delhi.
3. Sykes P “A Guide Book to Mechanism in Organic Chemistry”
6th Ed (1986) John Wiley & Sons Inc. New York.
4. Streitwieser JRA and Heathcock CH “Introduction to Organic
Chemistry” 3M Ed (1989) Macmillan Publishing Company, New York.
5. Furniss BS. Hannaford AJ, Smith PWGand Tatchell AR “Vogel’s
Textbook of Practical Organic Chemistry” 5th Ed (2000) Longman
Scientific & Technical, UK.
6. Arayne M.S. & Sultana “A Manual of Qualitative Organic
Analysis” 3rd Ed. (2006) BCCT University of Karachi.
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