Medical Chemistry II

Learning Objectives
A. Chapter 5, Orange Book
1. CIP Nomenclature: R/S and E/Z Priorities
2. Properties of Enantiomers (Reactions 5.1, 5.2)
3. Biological Activity of Enantiomers (p. 163)
4. Fisher Projections: Meaning of vertical bar and of horizontal bar
5. Meso-compounds: Definition
6. Racemic Mixture: Definition
B. Chapter 2, Orange Book
7. Newman projections: eclipsed, staggered (anti), gauche (2.8, p. 47)
8. Conformations of cyclohexane: chair, boat (2.9, pp.48-52)
9. Axial and Equatorial substituents (p. 52)
C. Chapter 7, Orange Book
10. Conversion to alkoxides (7.6)
11. Conversion to alkyl halides (7.9-7-10)
12. Dehydration to alkenes (7.8)
13. Oxidation of primary alcohols with PCC
14. Oxidation of primary alcohols with Jones reagent
15. Reaction of primary alcohols with PCl
3

16. Reaction of primary alcohols with PCl
5

17. Reaction of primary alcohols with SOCl
2

18. Oxidation of secondary alcohols with Jones reagent
19. Preparation of phenoxide (7.6)
20. Electrophilic Aromatic Substitution into phenols (7.14)
D. Chapter 10, Orange Book
18. Neutralization of carboxylic acids with bases
19. Hydrolysis of acyl chlorides (Table 10.5, p. 315)
20. Alcoholysis of acyl chlorides (Table 10.5, p. 315)
21. Ammonolysis of acyl chlorides (Table 10.5, p. 315)
22. Hydrolysis of acyl anhydrides (Table 10.5, p. 315)
23. Alcoholysis of acyl anhydrides (Table 10.5, p. 315)
24. Ammonolysis of acyl anhydrides (Table 10.5, p. 315)
25. Hydrolysis of esters (Table 10.5, p. 315)
26. Alcoholysis of esters (Table 10.5, p. 315)
27. Ammonolysis of esters (Table 10.5, p. 315)
28. Hydrolysis of amides (Table 10.5, p. 315)
29. Esterification of carboxylic acids
30. Ammonolysis of carboxylic acids (Table 10.5, p. 315)
E. Chapter 3, Groundwater
31. Acid catalysis: activation of nucleophilic center
32. Gem-diol
33. Gem-diol formation: acid catalysis
34. Gem-diol formation: base catalysis
35. Hemiacetal formation
36. Hemiketal formation
37. Cyanohydrin formation
38. Oximes: structure
39. Oxime formation
40. Imines and Schiffs bases: reaction of aldehydes or ketones with amines
41. Hydrazones: structure
42. Hydrazone formation
43. Properties of -Hydrogen
44. Aldol addition
45. Effect of a substituent at an -Carbon onto the reactivity of ketones
46. Keto-enol tautomerism
F. Chapter 13, Orange Book
47. Structure of Pyridine
48. Structure of Pyridazine
49. Structure of Pyrimidine
50. Structure of Pyrazine
51. Structure of Pyrrole
52. Structure of Furan
53. Structure of Thiophene
54. Structure of Imidazole
55. Structure of Oxazole
56. Structure of Thiazole
57. Structure of Quinoline
58. Structure of Isoquinoline
59. Structure of Indole
60. Structure of Purine
61. Structure of Pteridine
62. Structure of Cytosine
63. Structure of Thymine
64. Structure of Uracil
65. Structure of Adenine
66. Structure of Guanine
67. Structure of 3-picolines
68. Lactim-lactam tautomerism
69. Amino-imino tautomerism
70. Prototropic tautomerism
71. Electrophilic Aromatic Substitution into Pyridine
72. Nucleophilic Aromatic Substitution into Pyridine
73. Electrophilic Aromatic Substitution into Pyrrole
74. Electrophilic Aromatic Substitution into Quinolines
75. Oxidation of quinolone
G. Hydroxy and Keto Acids
76. IUPAC name of glycolic acid
77. Structure of lactic acid
78. IUPAC name of glycolic acid
79. Stereogenic center in glycolic acid
80. Structure of malic acid
81. IUPAC name of malic acid
82. Stereogenic center in malic acid
83. Structure of tartaric acid
84. IUPAC name of tartaric acid
85. Stereogenic centers in tartaric acid
86. Enantiomers of tartaric acid
87. Meso-tartaric acid
88. Structure of citric acid
89. IUPAC name of citric acid
90. Isomers of citric acid
91. -hydroxy acids
92. Lactide formation from -hydroxy acids
93. Reaction of -hydroxy acids at the presence of mineral acids
94. -hydroxy acids
95. Internal dehydration of -hydroxy acids
96. -hydroxy acids
97. Lactone formation from -hydroxy acids
98. Structure of glyoxalic (glyoxylic) acid
99. IUPAC name of glyoxalic (glyoxylic) acid
100. Structure of pyruvic acid
101. IUPAC name of pyruvic acid
102. Decarbonylation of pyruvic acid
103. Decarboxylation of pyruvic acid
104. Structure of formylacetic acid
105. IUPAC name of formylacetic acid
106. Structure of acetoacetic acid
107. IUPAC name of acetoacetic acid
H. Chapter 4, Orange Book
108. Benzene ring activating substituents: definition and examples
109. Benzene ring deactivating substituents: definition and examples
110. Ortho- and para-directing groups: examples
111. Meta-directing groups: examples
112. Charge distribution on a sigma-complex of electrophilic aromatic substitution into
benzene derivatives
I. Lipids
113. Fatty acids: definition and examples
114. Structure of palmitic acid
115. Structure of stearic acid
116. Structure of arachidic acid
117. Structure of palmitoleic acid
118. Structure of oleic acid
119. Structure of linoleic acid
120. Structure of linolenic acid
121. Structure of arachidonic acid
122. -symbols for fatty acids
123. Electrophilic addition of halogens to unsaturated fatty acids
124. Hydration of unsaturated fatty acids
125. Hydrogenation of unsaturated fatty acids
126. Classification of lipids: saponifiable and nonsaponifiable lipids
127. Classification of saponifiable lipids: simple and compound lipids
128. Fats: components and structural pattern
129. Biological function of fats
130. sn-nomenclature for fats
131. Waxes: components and structural pattern
132. Glycerophopholipids: components and structural pattern
133. Structure of phosphatidic acid
134. Structure of cephalins
135. Biological function of cephalins
136. Structure of lecithins
137. Biological function of lecithins
138. Structure of phosphatidylserines
139. Biological function of phosphatidylserines
140. Glyceroglycolipids: components and structural pattern
141. Hydrophobicity of phospholipids: polar head and non-polar tail
142. Structure of sphingosine
143. Ceramides: components and structural pattern
144. Sphingomyelin: components and structural pattern
145. Biological function of sphingomyelin
146. Galactocerebroside: components and structural pattern
147. Biological function of galactocerebroside
148. Glucocerebroside: components and structural pattern
149. Biological function of glucocerebroside
150. Steroids: classification of the rings
151. Steroids: 3
rd
, 10
th
and 17
th
positions
152. Steroids: angular methyl groups
153. Seco-steroids
154. Structure of cholesterol
155. Biological function of cholesterol
156. Structure of vitamin D2
157. Structure of prednisolone
158. Biological function of corticosteroids
159. Structure of estradiol
160. Biological function of estradiol
161. Structure of testosterone
162. Biological function of testosterone
J. Carbohydrates, Orange Book
163. Aldoses: definition and examples
164. Ketoses: definition and examples
165. Pentoses: definition and examples
166. Hexoses: definition and examples
167. L-hexoses: definition and examples
168. D-hexoses: definition and examples
169. L-pentoses: definition and examples
170. D-pentoses: definition and examples
171. Epimers: definition and examples
172. Open-chain structure of D-glucose
173. Open-chain structure of L-glucose
174. C-2 epimer of D-glucose
175. C-2 epimer of L-glucose
176. C-4 epimer of D-glucose
177. C-4 epimer of L-glucose
178. Reduction of hexoses
179. Oxidation of hexoses
180. Structure of sorbitol
181. Structure of mannitol
182. Structure of dulcitol
183. Structure of aldonic acids
184. Structure of aldaric acids
185. Structure of alduronic acids
186. Structure of gluconic acid
187. Structure of glucuronic acid
188. Structure of glucaric acid
189. Structure of mannonic acid
190. Structure of mannuronic acid
191. Structure of mandarin acid
192. Structure of galactonic acid
193. Structure of galacturonic acid
194. Structure of galactaric acid
195. Anomers: definition and examples
196. Pyranoses: definition and examples
197. Furanoses: definition and examples
198. Structure of -D-glucopyranose
199. Structure of -D-glucopyranose
200. Structure of -D-mannopyranose
201. Structure of -D-mannopyranose
202. Structure of -D-galactopyranose
203. Structure of -D-galactopyranose
204. Structure of -D-fructofuranose
205. Structure of -D-fructofuranose
206. Structure of -L-glucopyranose
207. Structure of -L-glucopyranose
208. Structure of -L-mannopyranose
209. Structure of -L-mannopyranose
210. Structure of -L-galactopyranose
211. Structure of -L-galactopyranose
212. Structure of -L-fructofuranose
213. Structure of -L-fructofuranose
214. Chair conformation of -D-glucopyranose
215. Chair conformation of -D-glucopyranose
216. Chair conformation of -D-mannopyranose
217. Chair conformation of -D-mannopyranose
218. Chair conformation of -D-galactopyranose
219. Chair conformation of -D-galactopyranose
220. Chair conformation of -D-fructofuranose
221. Chair conformation of -D-fructofuranose
222. Glycosidic bond: definition and examples
223. Structure of maltose
224. Structure of cellobiose
225. Structure of gentobiose
226. Structure of lactose
227. Structure of sucrose
228. Glycosidic bond in maltose
229. Glycosidic bond in cellobiose
230. Glycosidic bond in gentobiose
231. Glycosidic bond in lactose
232. Glycosidic bond in sucrose
233. Reducing sugars: definition and examples
234. Non-reducing sugars: definitions and examples
235. Composition of starch
236. Composition of glycogen
237. Structure of amylose
238. Structure of amylopectin
K. Amino Acids, Orange Book
239. -amino acids: definition and examples
240. proteinogenic amino acids: definition and examples
241. essential amino acids: definition and examples
242. The list of twenty proteinogenic amino acids
243. The list of ten essential amino acids
244. Structure of glycine
245. Structure of alanine
246. Structure of leucine
247. Structure of isoleucine
248. Structure of valine
249. Structure of serine
250. Structure of threonine
251. Structure of cysteine
252. Structure of methionine
253. Structure of phenylalanine
254. Structure of tyrosine
255. Structure of histidine
256. Structure of tryptophan
257. Structure of arginine
258. Structure of lysine
259. Structure of asparagine
260. Structure of aspartic acid
261. Structure of glutamine
262. Structure of glutamic acid
263. Structure of proline
264. Formation of diketopyperazines from -amino acids
265. Formation of lactams from -amino acids
266. Reducing deamination of -amino acids
267. Internal deamination of -amino acids
268. Hydrolytic deamination of -amino acids
269. Oxidation deamination of -amino acids
270. Transamination of -amino acids
271. Nynhydrin test
272. Van Slyke determination
273. Sorensens formol titration
274. Isoelectric point: definition
275. Zwitterion (dipolar ion) of an -amino acid
276. Structure of an -amino acid in acidic mediums
277. Structure of an -amino acid in alkaline mediums
278. Isoelectric point of alanine
279. Isoelectric point of lysine
280. Isoelectric point of aspartic acid