Chemistry for Pharmacy Students : General, Organic and Natural ...

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Recommended further reading RECOMMENDED FURTHER READING 15 pH Quantity to be used per Colour in Colour in Indicator range 10 mL acid base Bromophenol 3.0–4.6 1 drop of 0.1% aq. solution Yellow Blue–violet blue Methyl orange 3.1–4.4 1 drop of 0.1% aq. solution Red Orange Phenolphthalein 8.0–10.0 1–5 drops of 0.1% solution Colourless Red in 70% alcohol Thymol blue 1.2–2.8 1–2 drops of 0.1% aq. solution Red Yellow Ebbing, D. D. and Gammon, S. D. General Chemistry, 7th edn, Houghton Mifflin, New York, 2002.
Page 2 and 3: Chemistry for Pharmacy Students Gen
Page 4: This book is dedicated to pharmacy
Page 7 and 8: viii CONTENTS 5.5 Substitution reac
Page 9 and 10: x PREFACE countries. Therefore, the
Page 12 and 13: 1 Introduction Learning objectives
Page 14 and 15: Whatever the source is, chemistry i
Page 16 and 17: 1.2 PHYSICAL PROPERTIES OF DRUG MOL
Page 18 and 19: Each acid has a conjugate base, and
Page 20 and 21: 1.2 PHYSICAL PROPERTIES OF DRUG MOL
Page 22 and 23: CH3CH3 ðEthaneÞ !CH3NH2 ðMethyla
Page 24 and 25: takes place. K a ¼ K eq½H2OŠ ¼
Page 28 and 29: 2 Atomic structure and bonding Lear
Page 30 and 31: 2.2 ATOMIC STRUCTURE: ORBITALS AND
Page 32 and 33: 2.3 CHEMICAL BONDING THEORIES: FORM
Page 34 and 35: 2.3 CHEMICAL BONDING THEORIES: FORM
Page 36 and 37: hydrogen. In general, the first ion
Page 38 and 39: 2.4 ELECTRONEGATIVITY AND CHEMICAL
Page 40 and 41: 2.5.1 Dipole-dipole interactions Th
Page 42 and 43: 2.6 SIGNIFICANCE OF CHEMICAL BONDIN
Page 44: Many drugs are acids or amines, eas
Page 47 and 48: 36 CH3 STEREOCHEMISTRY 3.1 Stereoch
Page 49 and 50: 38 CH3 STEREOCHEMISTRY Eclipsed Sta
Page 51 and 52: 40 CH3 STEREOCHEMISTRY a flat or pl
Page 53 and 54: 42 CH3 STEREOCHEMISTRY R = Any subs
Page 55 and 56: 44 CH3 STEREOCHEMISTRY Optical isom
Page 57 and 58: 46 CH3 STEREOCHEMISTRY However, the
Page 59 and 60: 48 CH3 STEREOCHEMISTRY group. In th
Page 61 and 62: 50 CH3 STEREOCHEMISTRY A H O C H O
Page 63 and 64: 52 CH3 STEREOCHEMISTRY (b) If the t
Page 65 and 66: 54 CH3 STEREOCHEMISTRY One enantiom
Page 67 and 68: 56 CH3 STEREOCHEMISTRY reaction. Th
Page 69 and 70: 58 CH3 STEREOCHEMISTRY name for the
Page 71 and 72: 60 CH4 ORGANIC FUNCTIONAL GROUPS 4.
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66 CH4 ORGANIC FUNCTIONAL GROUPS 4.
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68 CH4 ORGANIC FUNCTIONAL GROUPS RH
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70 CH4 ORGANIC FUNCTIONAL GROUPS No
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72 CH4 ORGANIC FUNCTIONAL GROUPS de
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74 CH4 ORGANIC FUNCTIONAL GROUPS H
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76 CH4 ORGANIC FUNCTIONAL GROUPS Ac
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78 CH4 ORGANIC FUNCTIONAL GROUPS wo
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82 CH4 ORGANIC FUNCTIONAL GROUPS Al
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84 CH4 ORGANIC FUNCTIONAL GROUPS Pr
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86 CH4 ORGANIC FUNCTIONAL GROUPS Al
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88 CH4 ORGANIC FUNCTIONAL GROUPS R'
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90 CH4 ORGANIC FUNCTIONAL GROUPS O
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96 CH4 ORGANIC FUNCTIONAL GROUPS Ac
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98 CH4 ORGANIC FUNCTIONAL GROUPS ca
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100 CH4 ORGANIC FUNCTIONAL GROUPS A
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102 CH4 ORGANIC FUNCTIONAL GROUPS g
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104 CH4 ORGANIC FUNCTIONAL GROUPS t
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108 CH4 ORGANIC FUNCTIONAL GROUPS X
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110 CH4 ORGANIC FUNCTIONAL GROUPS C
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112 CH4 ORGANIC FUNCTIONAL GROUPS 4
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114 CH4 ORGANIC FUNCTIONAL GROUPS I
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116 CH4 ORGANIC FUNCTIONAL GROUPS N
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118 CH4 ORGANIC FUNCTIONAL GROUPS T
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120 CH4 ORGANIC FUNCTIONAL GROUPS w
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126 CH4 ORGANIC FUNCTIONAL GROUPS r
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128 CH4 ORGANIC FUNCTIONAL GROUPS C
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132 CH4 ORGANIC FUNCTIONAL GROUPS p
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142 CH4 ORGANIC FUNCTIONAL GROUPS +
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144 CH4 ORGANIC FUNCTIONAL GROUPS 4
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148 CH4 ORGANIC FUNCTIONAL GROUPS F
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154 CH4 ORGANIC FUNCTIONAL GROUPS R
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160 CH4 ORGANIC FUNCTIONAL GROUPS I
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164 CH4 ORGANIC FUNCTIONAL GROUPS b
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166 CH4 ORGANIC FUNCTIONAL GROUPS a
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168 CH4 ORGANIC FUNCTIONAL GROUPS r
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174 CH4 ORGANIC FUNCTIONAL GROUPS (
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176 CH4 ORGANIC FUNCTIONAL GROUPS p
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182 CH4 ORGANIC FUNCTIONAL GROUPS a
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184 CH4 ORGANIC FUNCTIONAL GROUPS o
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5 Organic reactions Learning object
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5.2 RADICAL REACTIONS: FREE RADICAL
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5.2 RADICAL REACTIONS: FREE RADICAL
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(BHA) and butylated hydroxytoluene
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CH 3 CH3CH2C CH2 2-Methyl-1-butene
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H CH3 C C H H + H Br C H 3 Br: −
Page 214 and 215:
Free radical addition of HBr to alk
Page 216 and 217:
Mechanism. C H 3 CH3 C CH2 H 2 SO 4
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CH 3 C 2-Butyne CCH 3 H 2 SO 4 H 2
Page 220 and 221:
H2SO4, produces ethers. Addition of
Page 222 and 223:
Addition of halides to alkynes: pre
Page 224 and 225:
If the nucleophile is a negatively
Page 226 and 227:
O H3O RCH2 MgX RCH2 C OMgX + CO _ 2
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to generate a four-membered ring, a
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+ O : O OH OH2 ± H R C Y R C Y R C
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: O: R C H H3O + .. + R H O H H3O R
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5.4 ELIMINATION REACTIONS: 1,2-ELIM
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5.4.3 Dehydration of alcohols: prep
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2-methyl shift to form a protonated
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C O K + CH(CH3 ) 2 (H3C) 2HC N H Po
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trans-diaxial positions, and chair-
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First order nucleophilic substituti
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less stable secondary cation. Rearr
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Nucleophilicity increases down the
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ether. The reaction involves SN2 di
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etter leaving group, and reacts wit
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Conversion of alcohols by thionyl c
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Similarly, alkyl tosylate reacts wi
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Preparation of alkoxy alcohol Acid-
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If the nucleophile is a neutral mol
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eaction stops at this point, since
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aldehydes, ketones, esters, amides
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Friedel-Crafts alkylation + E H E +
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electrophile, which is formed by th
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Mechanism. Step 1. Generation of ni
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Hydrolysis of acid halides and anhy
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.. : + O : OH OH H R C NH2 R C NH R
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5.7.1 Oxidizing and reducing agents
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5.7.5 Oxidative cleavage of syn-dio
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O i. O3 , -78 C2H5C CH C2H5 C OH oC
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5.7 OXIDATION-REDUCTION REACTIONS 2
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Preparation of alcohols: catalytic
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aldehyde or ketone to give hydrazon
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5.7.22 Reduction of esters Preparat
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Different types of cyclic compound
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5.8.2 Sigmatropic rearrangements Si
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6 Natural product chemistry Learnin
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6.1 INTRODUCTION TO NATURAL PRODUCT
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6.1 INTRODUCTION TO NATURAL PRODUCT
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origin. In most alkaloids, the nitr
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Pyrrole and pyrrolidine (Ornithine
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Hygrine Hygrine, molecular formula
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Quinine Quinine, molecular formula
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an antitussive for severe cough. Si
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H N Ergoline N H N H R H N D-Lyserg
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HO OMe N HO OMe O O OMe OMe Aconiti
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6.3 Carbohydrates Carbohydrates are
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HO NH 2 6 5 OH 4 3 2 1 H OH OH O Gl
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6.3.4 Mutarotation The term mutarot
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HO HO HO O OH OH β-D-Glucopyranose
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6.3.8 Pharmaceutical uses of monosa
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1,4 0 -linkage. Chemically, it can
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O O H HO O HO OHO O HO HO OH O O O
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protective colloid, binder, stabili
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6.3.12 Cell surface carbohydrates a
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HO HO HO Quercetin, a flavonoid (Ag
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should be restricted to short term
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HO HO OH Shikimic acid O O Alizarin
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Cardiac glycosides HOOC H O HO O HO
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6 7 8 10 5 9 11 4 3 O 1 8 5 4 3 O 1
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antioxidant, antiviral and antimicr
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O HO O HO HO OH HO OP 3R (+)-Mevalo
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Artemisia annua and ( )-a-bisabolol
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(Continued) Laurane sesquiterpenes
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(Continued) Xanthane sesquiterpenes
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(Continued) Isolactarane, merulane,
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6.5.5 Diterpenes The diterpenoids c
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Dolastane diterpenoids Eunicellane
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Common name Botanical name (Family)
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Pentacyclic triterpenes Friedelane
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compounds are important metabolites
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of steroids are named after their f
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often prescribed as a remedy for in
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It was discovered a relatively long
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Adrenocorticoid hormones are produc
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source of eugenol and star anise (I
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6.7.3 Coumarins The coumarins (2H-1
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Linear dihydropyranocoumarins Angul
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Classification Flavonoids can be cl
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are often present in unripe fruits,
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Index Acetal 220, 221, 307 Acetalde
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Bischler-Napieralski synthesis 166
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Diols (glycols) 75 Dipeptide 180 Di
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Hydrogen cyanide 217 Hydrogenation
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Oestrone (estrone) 358 Oleaceae 330
Page 392 and 393:
Rosaceae 321, 326 Rutaceae 334, 363
Page 394:
Wittig reaction 215-217 Wolff-Kishn
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