Download Aldehydes and Ketones - Study Notes Review for Final Exam | CHEM 2380 and more Exams Organic Chemistry in PDF only on Docsity! CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 1 (Solomons) CHAPTER 16 ALDEHYDES & KETONES - INTRODUCTION, NOMENCLATURE - PHYSICAL PROPERTIES - SYNTHESIS OF : - RCHO - RCOR’ - REACTIONS: ADDITION TO ( C = O ) GROUP - GENERAL MECHANISM - ADDITION OF : - ROH - NH3 - HCN - YLIDES ( WITTIG REACTION ) - R-M REAGENT - OXIDATION - ANALYSIS: - CHEMICAL - SPECTRAL CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 2 (Solomons) INTRODUCTION R C H O R C R' O ALDEHYDE KETONE ALKANAL ALKANONE - SEE e.g. p. 687, 688 - DO PROBLEMS: 16.1, p. 687 16.19 p. 725 PHYSICAL PROPERTIES - SEE p. 689 - DO PROBLEM : 16.2 p. 689 - SEE TABLE 16.1 p. 689 SYNTHESIS OF ALDEHYDES: 1] FROM: R-CH2OH - REAGENT(S) = ? CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 5 (Solomons) REACTIONS : ADDITION TO ( C = O ) - NUCLEOPHILIC ADDITION [ cf. ADDITION TO ( C = C ) ] - GENERAL REACTION p. 696 - MECHANISMS : - STRONG NUCLEOPHILES p. 697 - Nu: ADDS FIRST - WEAK NUCLEOPHILES p. 697 - H+ ADDS FIRST (ACID – CATALYZED ADDITION) - WHY ? - ADDITION OF R – OH - HEMIACETALS [ HEMIKETALS ] - –OH AND –OR ATTACHED TO THE SAME CARBON - ACETALS [KETALS ] - TWO –OR GROUPS ATTACHED TO THE SAME CARBON - SEE p. 699 – 703 - CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 6 (Solomons) - EXAMINE GLUCOSE , SUCROSE - p 699, 702 - SEE MECHANISM p 699 – 703 - NOTE: ALL STEPS REVERSIBLE - SO ? - POSSIBLE TO MANIPULATE DIRECTION OF REACTION - USEFUL PROTECTING GROUPS: - ADD / REMOVE EASILY - ACETALS STABLE IN BASIC SOLUTIONS, BUT HYDROLYZE IN ACIDIC SOLUTIONS - GO THROUGH SECTIONS 16.7 C,D ON YOUR OWN: p 704 – 705 - IMPORTANT APPLICATION: - ALTERNATIVE METHOD FOR >C=O [ THIOACETAL ] >CH2 HOW ? - RANEY Ni , H2 ( cf. REACTION CONDITIONS FOR CLEMMENSEN REDUCTION ) CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 7 (Solomons) - REACTION OF AMMONIA DERIVATIVES: A] 10 AMINES : - “R” – NH2 - SEE MECHANISM p. 706 1] NUCLEOPHILIC ADDITION FOLLOWED BY 2] SPONTANEOUS ELIMINATION OF WATER - FINAL PRODUCT : IMINE - CAN EXIST AS E, Z, ISOMERS - SEE TABLE 16.2, p. 707 - LOOK FOR COMMON FEATURES - “ R ” = ? - NAMES OF AMINE REACTANTS / IMINE PRODUCTS ? [ LEARN !!] B] 20 AMINES : - R – NH – R - SEE MECHANISM p. 709 ( cf. MECHANISM FOR IMINE FORMATION, p 706 ) CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 10 (Solomons) - DO PROBLEM : 16.17, 16.18 p. 715 - ADDITION OF R – M: - RMgX , RLi , R-C≡C: – Na+ - REVIEW ! OXIDATION - ALDEHYDES ACIDS R C O H R O C HO - HOW ? A] i) KMnO4 , OH - ii) H3O + B] i) Ag2O , OH - ii) H3O + ( “ SILVER MIRROR ” / TOLLEN’S TEST ) CHEM 2380 DANDEKAR CHAPTER 16 (9th ed) 11 (Solomons) ANALYSIS - CHEMICAL: - AMMONIA DERIVATIVES ALDEHYDES AND KETONES: - TOLLEN’S “ SILVER MIRROR ” TEST ALDEHYDES ONLY SPECTROSCOPY REVIEW !
