Since the nature of nitogen in Tropine was found as tertiary so there should be an ester linkage Structure determination of Atropine DBEs 7 Structure determination of Tropic acid Functional group test DBEs 5 ID: 1038470
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1. Atropine
2. Nature of linkage could be amide or ester!!!Since the nature of nitogen in Tropine was found as tertiary, so there should be an ester linkage.Structure determination of AtropineDBEs = 7
3. Structure determination of Tropic acidFunctional group test: DBEs = 5Presence and number of –COOH group: Present, 1 numberPresence and number of –OH group: Present, 1 numberNature of –OH group : Primary
4. Atropic acid was formed by the dehydration of Tropic acid, so the structure of Tropic acid could be either II or IV. Structure IV was confirmed as Tropic acid. Structure determination of Tropic acid
5. Synthesis of Tropic acidMuller and Wislicenus synthesis
6. Structure determination of TropineDBEs = 2FG test:Nature of nitrogen- tertiary, N-CH3 group present-OH group present, nature of OH- secondary alcoholLadenburgBased on these observations Ladenburg proposed following two structures of Tropine but both were incorrectas Tropine do not add on the bromine.
7. Structure determination of TropineMerlingOxidation (degradation) studiesTropinic acid and Tropine have same number carbons so Merling suggested that -OH group must be present on a ring and he proposed following two saturated structures of Tropine.WillstatterReinvestigated the oxidation of TropineIsolation of Tropinone (a ketone) confirmed the nature of –OH as secondary.Isolation of N-methylesuccinimide confirmed the presence of 5-membered heterocycle. N-atom must be common to both piperidine (6-memb) as well as pyrrolidine (5-memb) ring since there is only one N-atom in Tropine.
8. Structure determination of TropineWillstatterDerivatization of Tropinone confirmed the presence of –CH2-CO-CH2- moiety in Tropine.Based on these observations he modified Merlings structure and proposed folloing structure which was found correct by further degradation studies.
9. Reactions of Tropine
10. Synthesis of TropineRobinson’s synthesisSingle step synthesis
11. Preparation of Atropine
12. Stereochemistry of TropineFodor’s stereochemistry of Tropine: Proposed boat conformer of Tropine moiety in AtropineBose’s stereochemistry of Tropine: Proposed chair conformer of Tropine moiety in Atropine