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Unformatted text preview: 4. 4. Complete reactions involving nucleophilic addition to the C=O bond: addition of a) a) H 2 O, ROH b) b) Various ammonia derivatives c) c) HCN and NaHSO 3 d) d) phosphorus ylides (Wittig reaction) e) e) organometallic reagents (RC = C:- Na + , RLi, RMgX, RZnBr) 5. 5. Oxidize aldehydes to carboxylic acids with alkaline KMnO 4 , alkaline Ag 2 O (Tollen’s reagent). 6. 6. Oxidize ketones to esters with peroxy acids (Baeyer-Villiger oxidation): predict major product based on migratory aptitude. 7. 7. Distinguish between aldehydes and ketones by comparing ease of oxidation with alkaline Ag 2 O via the Tollen’s (silver mirror) test. 8. 8. Use spectral data for structure elucidation of aldehydes and ketones. REACTION MECHANISMS 1. 1. Nucleophilic addition to C=O (strong, weak nucleophiles) 2. 2. Wittig reaction 3. 3. Reformatsky reaction 4. 4. Baeyer-Villiger oxidation...
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