OBJECTIVESCHAPTER 16

OBJECTIVESCHAPTER 16 - 4 4 Complete reactions involving nucleophilic addition to the C=O bond addition of a a H 2 O ROH b b Various ammonia

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OBJECTIVES CHAPTER 16 TERMS: Definitions, examples, and brief explanations 1. 1. Aldehyde hydrate 2. 2. Hemiacetal, hemiketal 3. 3. Acetal, ketal 4. 4. Keto-enol tautomerization 5. 5. Oxime 6. 6. Hydrazone (phenylhydrazone, 2,4-dinitrophenylhydrazone) 7. 7. Semicarbazone 8. 8. Cyanohydrin 9. 9. Wolff-Kishner reduction 10. 10. Reformatsky reaction 11. 11. Phosphorus ylides 12. 12. Wittig reaction 13. 13. Migratory aptitude of various groups 14. 14. Baeyer-Villiger oxidation 15. 15. Tollen’s test KNOW HOW TO: 1. 1. Use rules of nomenclature for compounds containing aldehyde and ketone functional groups. Know priority order of various groups for numbering parent systems of multifunctional compounds. 2. 2. Synthesize aldehydes from a) a) 1 o alcohols by oxidation b) b) acid derivatives such as RCOX, RCO 2 R’ and RCN by reduction c) c) ozonolysis of alkenes 3. 3. Synthesize ketones from a) a) 2 o alcohols by oxidation b) b) Friedel-Crafts acylation c) c) hydration of alkynes
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d) d) ozonolysis of alkenes e) e) R 2 CuLi + R’COCl f) f) RLi + R’CN
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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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This note was uploaded on 04/14/2008 for the course CHEM 2380 taught by Professor Dandekar during the Winter '07 term at North Texas.

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OBJECTIVESCHAPTER 16 - 4 4 Complete reactions involving nucleophilic addition to the C=O bond addition of a a H 2 O ROH b b Various ammonia

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