Pharmaceutical Organic Chemistry for IIIrd Semester B.Pharmacy Course IV Semester Dr. S.C. SHARMA Dr. RAJ KUMAR M.Sc., Ph.D. M.S. (Pharm.), Ph.D., Postdoc (U.S.A.) Former-Head Deptt. of Chemistry Assistant Professor, V.B.R.I. P.G. College, ISF College of Pharmacy, UDAIPUR (Rajasthan) MOGA (Punjab) Future for WINNERS VISHAL PUBLISHING CO. JALANDHAR DELHI
CONTENTS 1. HETEROCYCLIC CHEMISTRY 1 34 1.0. Introduction (1) 1.1. Nomenclature (2) 1.2. Five-membered rings (3) (A) Furan (3) (B) Thiophene (7) (C) Pyrrole (9) (D) Imidazole (12) (E) Oxazole (13) (F) Thiazole (14) (G) Phenothiazine (14) 1.3. Six-membered heterocycles with one hetero atom (17) (A) Pyridine (Azine), C 5 H 5 N (17) 1.4. Condensed heterocyclic compounds containing one hetro atom (24) (A) Quinoline (, -Benzopyridine) (24) (B) Isoquinoline, (4, 5-Benzopyridine) (27) Questions (33-34) 2. CARBOHYDRATES 35 71 2.0. Introduction (35) 2.1. Definition (35) 2.2. Classification (35) 2.3. Reducing and non-reducing sugars/ carbohydrates (36) 2.4. Configuration of aldotriose and aldopentoses (36) 2.5. Introduction (37) 2.6. Glucose (dextrose, grape sugar, corn sugar, blood sugar), C 6 H 12 O 6 (37) 2.6.1. Occurrence (37) 2.6.2. Manufacture (38) 2.6.3. Physical properties (39) 2.6.4. Uses (39) 2.6.5. Structure elucidation of glucose (39) 2.6.6. Chemical properties (46) 2.7. Fructose (Laevulose, fruit sugar), C 6 H 12 O 6 (50) 2.7.1. Occurrence (50) 2.7.2. Manufacture (50) 2.7.3. Physical properties (50) 2.7.4. Structure (50) 2.7.5. Chemical properties (52) 2.8. The Kiliani-Fischer synthesis (Ascending the series of aldoses) (53) 2.9. The Ruff degradation (Chain shortening) (55) 2.10. Wohl degradation (55) 2.11. Epimerisation of an aldohexose (Conversion of D(+)-glucose into D(+)- mannose) (55) 2.12. Conversion of an aldohexose into ketohexose (56) 2.13. Conversion of a ketohexose into an aldohexose (say, conversion of fructose into glucose) (56) 2.14. Glycosides (56) 2.15. Introduction (57) 2.16. (+)-Sucrose (cane sugar), C 12 (58) 2.16.1. Properties (58) 2.16.2. Uses (58) 2.16.3. Structure (58) 2.17. (+)-Maltose, C 12 (m.pt. 102-103 C) (60) 2.17.1. Structure (60)
2.18. (+)-Lactose (milk sugar), C 12 (m.pt. 252 C) (62) 2.18.1. Manufacture (62) 2.19. (+)-Cellobiose (63) 2.19.1. Structure (63) 2.20. Introduction (64) 2.21. Starch (amylum), (C 6 H 10 O 5 ) n (64) 2.21.1. Manufacture (64) 2.21.2. Properties (64) 2.21.3. Structure (65) 2.21.4. Uses (67) 2.22. Cellulose (C 6 H 10 O 5 ) n (67) 2.22.1. Preparation (67) 2.22.2. Structure (68) 2.22.3. Industrial uses of cellulose (68) 2.23. Analysis of Carbohydrates (69) Questions (70-71) 3. AMINO ACIDS AND PROTEINS 72 97 3.0. Introduction (72) 3.1. Natural -amino acids and their configuration (73) 3.1.1. Essential (indispensable) and non-essential (dispensable) amino acids (73) 3.1.2. Preparation of -amino acids (74) 3.1.3. Structure of amino acids (isoelecric point/ zwitterion) (77) 3.1.4. Physical properties (78) 3.1.5. Chemical properties (78) 3.2. Peptides : structure and geometry (80) 3.3. Synthesis of peptides (81) 3.4. Proteins (84) 3.4.1. Classification (84) 3.4.2. General properties (86) 3.4.3. Analysis/colour reactions of proteins (87) 3.4.4. Determination of structure of proteins/ polypeptides (89) 3.4.5. Types of structures of protein (91) Questions (95-97) 4. NUCLEIC ACIDS 98 108 4.0. Introduction (98) 4.1. Structure (98) 4.1.1. Purine and pyrimidine bases (99) 4.1.2. Nucleosides (heterocyclic base + pentose sugar) (99) 4.1.3. Nucleotides (nucleoside + phosphate) (101) 4.1.4. Nucleotide polymers (102) 4.2. Structure of DNA and its role in heredity (103) 4.2.1. DNA replication (105) 4.3. Ribonucleic acid (RNA) vs deoxyribonucleic acid (DNA) (106) 4.4. Types of RNA (106) 4.4.1. Synthesis of mrna (transcription) (106) 4.4.2. Genetic code and biosynthesis of proteins (translation) (106) Questions (107-108) 5. AMINO ACIDS AND PROTEINS 109 120 5.0. Introduction (109) 5.1. Biological functions (109) 5.2. Types/classification (109) 5.3. Fats and oils (111) 5.3.1. Common fatty acids present in fats and oils (112) 5.3.2. Extraction and refining of oils (113) 5.3.3. General physical properties (113) 5.3.4. General chemical properties and industrial importance (113)
5.4. Anaylsis/identification of fats and oils (115) 5.4.1. Acid value (115) 5.4.2. Saponification value (116) 5.4.3. Iodine value or number (116) 5.4.4. Reichert-Meissl value (R.M. value) (117) 5.5. Uses (117) 5.6. Fixed versus volatile oils (essential oils) (118) 5.7. Mineral oils (118) 5.8. Drying oils (118) Questions (119-120) 6. XANTHINE DERIVATIVES 121 126 6.1. Xanthine (121) 6.1.1. Xanthine derivatives (122) 6.2. Caffeine (1,3,7-trimethyl xanthine) (122) 6.3. Theophylline (1,3-dimethylxanthine) (124) 6.4. Theobromine (3, 7-dimethylxanthine) (125) Questions (126) 7. COUMARINS 127 129 7.1. Coumarins (127) 7.1.1. Occurrence (127) 7.1.2. Structure (127) 7.1.3. Synthesis of Coumarins (127) 7.1.4. Reaction (127) 7.1.5. Naturally occurring coumarin derivatives (examples) (128) 7.1.6. Uses (128) Questions (129) 8.1. Isomerism (130) 8.2. Preparation/formation (130) 8.3. Aryl halides vs. alkyl halides (133) 8.4. General physical properties (133) 8.5. General chemical properties (134) 8.5.1. Nucleophilic aromatic substitution reactions (134) 8.5.2. Formation of Grignard reagent (141) 8.5.3. Wurtz-Fittig reaction (141) 8.5.4. Ullmann diaryl synthesis (141) 8.5.5. Reduction (141) 8.5.6. Formation of DDT (141) 8.5.7. Electrophilic aromatic substitution reactions (142) 8.6. Aryl vs vinyl halides (142) Questions (143-144) 9. -UNSATURATED CARBONYL COMPOUNDS 145 154 9.0. Introduction (145) 9.1. Reactions of, -unsaturated carbonyl compounds (146) (A) Electrophilic addition (146) (B) Nucleophilic addition (147) (C) The Michael addition (148) (D) The Diels-Alder reaction (150) Questions (154) OBJECTIVE TYPE QUESTIONS 155 161 SAMPLE QUESTION PAPERS 162 167 8. ARYL HALIDES 130 144 8.0. Introduction (130)