Organic Chemistry for Undergraduates - Volume - I

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I am pleased to present the book on Organic Chemistry for Undergraduates: Volume I in the hands of students learning organic chemistry at undergraduate level and the teachers of organic...

Name : Organic Chemistry for Undergraduates - Volume - I
Vendor : Prashant Publication
Type : Unknown Type
Barcode : 9788197627354

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Authors:

M T Chaudhari

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INTERNATIONAL	XS	S	M	L	XL	XXL	XXXL
EUROPE	32	34	36	38	40	42	44
US	0	2	4	6	8	10	12
CHEST FIT (INCHES)	28"	30"	32"	34"	36"	38"	40"
CHEST FIT (CM)	716	76	81	86	91.5	96.5	101.1
WAIST FIR (INCHES)	21"	23"	25"	27"	29"	31"	33"
WAIST FIR (CM)	53.5	58.5	63.5	68.5	74	79	84
HIPS FIR (INCHES)	33"	34"	36"	38"	40"	42"	44"
HIPS FIR (CM)	81.5	86.5	91.5	96.5	101	106.5	111.5
SKORT LENGTHS (SM)	36.5	38	39.5	41	42.5	44	45.5

I am pleased to present the book on Organic Chemistry for Undergraduates: Volume I in the hands of students learning organic chemistry at undergraduate level and the teachers of organic chemistry. The book is written by keeping in mind curriculum of organic chemistry prescribed by UGC taught at different levels through different papers.
Organic chemistry is the core part of curriculum of chemistry. Therefore, there is need of understanding it from very basics. The book focuses on understanding the principles involved, structures of organic compounds, nomenclature of compounds and organic reactions. The book aims to explain reactions of different functional groups with simple examples. The content of this book attempts to clarify the fundamentals of the subject without going through exhaustive details.
The book has eleven chapters including first chapter on Introduction to organic chemistry followed by chapter of Hydrocarbons. Study of different functional groups is included in next five chapters. The important topics like Heterocyclic compounds, synthetic reagents, organometallic compounds and stereoisomerism are also included in the first volume of the book.
To develop interest of learners, solved problems are given wherever necessary. At the end of each chapter, multiple choice questions, short answer questions and long answer questions are also given.
Considering the depth of students, book is written in very simple language and unnecessary explanation is avoided. It will definitely generate interest of the learner in understanding of the subject. I hope this book will be useful for the undergraduate students of chemistry.

1. Introduction to Organic Chemistry.......................1
Introduction, general properties of organic compounds, applications of organic compounds in everyday life. Covalent bond, double and triple bonds, structural formulae of organic compounds.
Structure of benzene, stability of benzene, Huckel’s rule of aromaticity, derivatives of benzene and their nomenclature.
Structural effects: Inductive effect, resonance hyperconjugation, steric effect, electromeric effect and their effect on the strength of acids and bases.
Fundamentals of organic reaction mechanism: Fission of covalent bond: homolytic and heterolytic fission, reactive intermediates: carbocations, carbanions and carbon free radicals, types of reagents: electrophiles and nucleophiles, types of organic reactions: addition, elimination, substitution and rearrangement reactions.
Isomerism, types of isomerism, structural isomerism.
Purification of organic compounds: recrystallization, distillation and sublimation.
Solvents, properties of solvents, types of solvents i) protic and aprotic ii) polar and nonpolar.

2. Hydrocarbons..............................................45
Alkanes: Introduction to alkanes and cycloalkanes, SP3 hybridization in ethane molecule, nomenclature, isomerism in alkanes.
Preparation of alkanes: by Wurtz reaction, hydrogenation of alkenes. Reactions of alkanes: by halogenation, nitration, combustion.
Alkenes: Introduction, SP2 hybridization in ethylene molecule, nomenclature, geometrical isomerism.Preparation of alkenes: by dehydration of alcohols, dehydrohalogenation of alkyl halides, dehalogenation of vicinal dihalides and partial reduction of alkynes by Lindlar catalyst. Reactions of alkenes: Addition of halogen, hydrogen halide, Sulphuric acid and hydration.
Alkynes: Introduction, SP hybridization in acetylene molecule, nomenclature, acidity of acetylene and terminal alkynes.
Preparation of alkynes: by Double Dehydrohalogenation of vicinal and geminal dihalides, by alkylation of acetylene.
Reactions: Addition of halogens, hydrogen halides, hydration, hydrogenation, ozonolysis.

3. Haloalkanes and Haloarenes..........................88
Haloalkanes: Introduction, classification and nomenclature of haloalkanes.
Mono halogen derivatives: Classification, methods of preparation: from alcohols by using HX, PX3, PX5 and SOCl2. Reactions: with aqueous alkali, sodium alkoxide, alc. KCN, silver salt of acid, alc. ammonia, NaSH/KSH, dehydrohalogenation, formation of Grignard’s reagent.
Di halogen derivatives: preparation of vicinal and geminal dihalides, reactions: hydrolysis with aq. NaOH.
Haloarenes: Introduction, nomenclature, reactions of haloarenes: nucleophilic substitution reactions with NaNH2/ KNH2, NaOH, NH3, CuCN, Ullman reaction.

4. Alcohols, Phenols and Ethers..................................114
Alcohols: Introduction, classification, nomenclature, methods of preparation of monohydric alcohols: from Grignard’s reagent, by reduction of aldehydes and ketones, by hydroboration, by oxymercuration-demercuration. preparation of dihydric alcohols by hydroxylation of alkenes.
Physical properties of alcohols. Reactions of alcohols: reaction with active metals, dehydration, oxidation and ester formation.
Phenols: Introduction, nomenclature, acidity of phenols, Preparation of phenol from benzene sulphonic acid, benzene diazonium chloride and from chlorobenzene.
Reactions of phenols: ester formation, formation of aryl ethers, Kolbe reaction, catalytic hydrogenation.
Ethers: Introduction, classification, nomenclature, methods of preparation: by Williamson’s synthesis, by dehydration of alcohols and from diazomethane. Reactions of ethers: reaction with hot and cold HI, hydrolysis with dil. H2SO4. Crown ethers.

5. Aldehydes and Ketones................................151
Introduction, structure of carbonyl group, nomenclature of aldehydes and ketones.
Aldehydes : Preparation of aldehydes: by reduction of acid chlorides, from Grignard’s reagent and HCN, from terminal geminal dihalides and from calcium salt of acids. Preparation of benzaldehyde: by Gattermann Kotch reaction, by oxidation of toluene, by side chain chlorination of toluene.
Ketones: Preparation from Grignard’s reagent and R-CN, from nonterminal geminal dihalides, from calcium salt of acids. Preparation of acetophenone: by oxidation of ethyl benzene, by F C acylation.
Reactions of aldehydes & Ketones: Reducing properties of aldehydes: reaction with Tollen’s reagent and Fehling’s solution, Clemmenson reduction, Wolff Kishner reduction, Aldol condensation, Cannizzaro reaction, addition of HCN, NaHSO3, addition of derivatives of ammonia (hydroxyl amine, phenyl hydrazine, 2,4 DNP, semicarbazide), hydration, addition of alcohols, benzoin condensation of benzaldehyde.

6. Carboxylic Acids and Their Deriatives ............180
Carboxylic acids: Introduction, nomenclature, preparation of carboxylic acids: by carbonation of Grignard’s reagent, and by hydrolysis of nitriles. Physical properties of acids, acidity of carboxylic acids. Reactions of carboxylic acids: formation of salt (with NaOH, KOH, Na2CO3, NaHCO3, NH4OH and active metals), Hell- Volhard- Zelinsky reaction, formation of acid anhydrides.
Aromatic carboxylic acids: Preparation of benzoic acid: by hydrolysis of phenyl cyanide and by carbonation of Grignard’s reagent. Reactions of benzoic acid: formation of salt, benzoyl chloride, benzamide and reduction to benzyl alcohol.
Esters: Preparation of esters- from alcohol & acid, alcohols & acid chloride, alkaline and acidic hydrolysis of esters.
Acid chlorides: preparation of acid chlorides from carboxylic acids by using PCl3, PCl5, SOCl2. Reactions of acid chlorides with benzene and with sodium salt of acids.
Amides: Preparation of amides from acid and ammonia and from acid chloride and ammonia. Reactions of amides: hydrolysis and Hofmann rearrangement.

7. Amines.............................................206
Introduction, classification, nomenclature, preparation of amines: by reduction of nitro alkanes, nitriles and oximes, by alkylation of primary and secondary amines, by reduction of isocyanides. Basicity of amines, reactions: action of nitrous acid, acylation, carbyl amine test, Hinsberg’s test.
Aromatic amines: Preparation of aniline: from chlorobenzene and from nitrobenzene. Basicity of aromatic amines. Reactions: benzoylation and N- alkylation. Preparation of benzene diazonium chloride, reactions of benzene diazonium chloride: formation of iodobenzene, Sandmeyer reaction, azo coupling reaction: formation of methyl orange.

8. Heterocyclic and Polycyclic Aromatic Compounds........................226
Five membered rings with one heteroatom: Introduction, preparation of furan, pyrrole and thiophene. Reactions: nitration, sulphonation, F C acylation, Reimer Tiemann reaction, catalytic hydrogenation.
Six membered rings with one heteroatom
Preparation of pyridine: from acrolein and from acetylene. Reactions: nitration, sulphonation, bromination, catalytic hydrogenation.
Polycyclicaromatic compounds: Introduction, structure of naphthalene, Haworth synthesis. Reactions: oxidation, reduction, nitration, halogenations, sulphonation, F C acylation.

9. Synthetic Reagents (Active methylene compounds)........................249
Introduction, active methylene group Acetoacetic ester: Preparation of acetoacetic ester. Synthesis of- alkyl acetic acid, dialkyl acetic acid, succinic acid, adipic acid, ∝-β unsaturated acid, methyl ketone (butanone).
Malonic ester: Preparation of malonic ester. Synthesis of- alkyl acetic acid, dialkyl acetic acid, succinic acid, glutaric acid, β keto acid (acetoacetic acid), ∝-β unsaturated acid.

10. Organometallic Compounds ................271
Nomenclature of organometallic compounds, carbon-metal bond in organometallic compounds.
Organolithium compounds: Preparation of organolithium compounds, Preparation of alcohols from organolithium compounds.
Organomagnesium compounds: Preparation of Grignard’s reagent, reactions of Grignard’s reagent with esters, acid chlorides, with compounds containing active hydrogen.
Organocopper compounds: Preparation of organocopper compounds (Lithium dialkylcuprate) and synthesis of alkanes.
Organozinc compounds: Preparation of organozinc compounds, synthesis of cyclopropanes (Simmon Smith reaction), Reformatsky reaction.

11. Stereoisomerism............................................281
Isomerism, classification of isomerism, stereoisomerism, types of stereoisomerism.
Projection formulae- Fischer projection formula, Newman projection formula, Saw horse formula.
Optical isomerism- Optical activity, enantiomerism, chiral center and chirality, elements of symmetry, dextrorotatory, levorotatory, Configuration: R and S nomenclature system.
Geometrical isomerism- Geometrical isomers, condition for geometrical isomerism, nomenclature systems: Cis and Trans, E and Z, Syn and Anti.
Conformational isomerism- Conformational isomers, conformational isomerism in ethane and n- butane with energy profile diagrams.
Stereochemistry of Cyclohexane - Conformations of cyclohexane: chair and boat forms, axial and equatorial bonds in cyclohexane, factors affecting stability of conformations. Mono substituted cyclohexane.