厦门大学化学化工学院：《有机化学》课程教学资源（课件讲稿，双语版）第十二章 由羰基化合物生成醇氧化还原反应和有机金属化合物（12.1-12.3）Introductionchpt12_1

Chapter 12 ALCohols From Carbonyl Compounds. Oxidation-Reduction and Organometallic Compounds 由羰基化 氧化还原反应有命属化合物

由羰基化合物生成醇 氧化还原反应和有机金属化合物

ORGANIC CHEMISTRY Chapter 12 12. 1 Introduction Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.1 Introduction

ORGANIC CHEMISTRY Chapter 12 Carbonyl compounds are a broad group of compounds that includes aldehydes, ketones carboxylic acids, and esters R R R R C=0 C=0 C=0 C=0 C=0 H R HO RO The carbonyl An aldehyde a ketone a carboxylic a carboxylate group ac ester Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 Carbonyl compounds are a broad group of compounds that includes aldehydes, ketones, carboxylic acids, and esters. C O C O H R C O R' R C O HO R C O R'O R The carbonyl group An aldehyde A ketone A carboxylic acid A carboxylate ester

ORGANIC CHEMISTRY Chapter 12 12. 1A Structure of the Carbonyl Group 120°%,8.8 C三0 120 Carbonyl group +-0:H H2C、+ -O Resonance structures for H2C Formaldehyde the carbonyl group Acetone H=2.27D =28D Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.1A Structure of the Carbonyl Group C O δ+ δ− sp2 Carbonyl group 120 120 C O C O Resonance structures for the carbonyl group C O H H C O H3C H3C Formaldehyde Acetone µ = 2.27 D µ = 2.88 D

ORGANIC CHEMISTRY Chapter 12 12.1b Reactions of Carbonyl Compounds with nucleophiles o From a synthetic of view, one of the most important reactions of carbonyl compounds is one in which the compound undergoes nucleophilic addition l+C=0 Nu-c-o Nu o Two im portant nucleo i hiles o Hydride ions(h) from NaBHa or LialH4 o Carbanions(rch2)from RLi or RMgx Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.1B Reactions of Carbonyl Compounds with Nucleophiles From a synthetic of view, one of the most important reactions of carbonyl compounds is one in which the compound undergoes nucleophilic addition. C O Nu δ δ + Nu C O Two important nucleophiles: Hydride ions (Hˉ) from NaBH4 or LiAlH4 Carbanions (RCH2 ˉ) from RLi or RMgX

ORGANIC CHEMISTRY Chapter 12 g Another related set of reactions are reactions in which alcohols and carbonyl compounds are oxidized and reduce [O] H oxidation R R-C-O-H C=O reduction H H THI A primal An aldehyde acoh Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 Another related set of reactions are reactions in which alcohols and carbonyl compounds are oxidized and reduced C O H R H H C O H oxidation R reduction [O] [H] A primary alcohol An aldehyde

ORGANIC CHEMISTRY Chapter 12 12.2 Oxidation-Reduction reactions in Organic Chemistry Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 12.2 Oxidation-Reduction Reactions in Organic Chemistry

ORGANIC CHEMISTRY Chapter 12 Reduction o Reduction of an organic molecules usually corresponds to increasing its hydrogen content or to decreasing its oxygen content. Oxygen content decreases O R-C-OH reduction R-C-H Carboxylic acid Aldehyde Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 Reduction Reduction of an organic molecules usually corresponds to increasing its hydrogen content or to decreasing its oxygen content. Oxygen content decreases R C OH O C O reduction R H [H] Carboxylic acid Aldehyde

ORGANIC CHEMISTRY Chapter 12 Hydrogen content increases O [ R-C-H R-CH OH reduction Aldehyde Alcohol Oxygen content decreases R-CHo OH R-CH reduction Alcohol Alkane Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 Hydrogen content increases C O R H Aldehyde reduction [H] R CH2 OH Alcohol reduction [H] R CH2 OH Alcohol R CH3 Alkane Oxygen content decreases

ORGANIC CHEMISTRY Chapter 12 Oxidation o Increasing the oxygen content of an organic molecule or decreasing its hydrogen content is an oxidation O R-CH3+R-CH2OH =R-C-H=R-C-OH Lowest Highest oxidation oxidation state state Department of Chemistry, Xiamen University

ORGANIC CHEMISTRY Department of Chemistry, Xiamen University Chapter 12 Oxidation Increasing the oxygen content of an organic molecule or decreasing its hydrogen content is an oxidation R C OH O C O R CH3 R CH2OH R H [H] [O] [H] [O] [H] [O] Highest oxidation state Lowest oxidation state