Chapter 11. Alcohols from carbonⅤ I compounds (由羰基化合物制醇). Oxidation-reduction and organometallic compounds (氧化还原和有机金属化合物) 11.1 Introduction Carbonyl(4E) compounds are a broad group of compounds that includes aldehydes, ketones, carboxylic acids and esters R R H R RO The carbonyl group An aldehyde A ketone A carboxylic acid A carboxylate ester 羰基 醛 酮 羧酸 酯
Chapter 11. Alcohols from carbonyl compounds (由羰基化合物制醇）. Oxidation-reduction and organometallic compounds (氧化-还原和有机金属化合物） 11.1 Introduction Carbonyl (羰基）compounds are a broad group of compounds that includes aldehydes, ketones, carboxylic acids, and esters. O The carbonyl group R H O R R' O R HO O R R'O O An aldehyde A ketone A carboxylic acid A carboxylate ester 羰 基 醛 酮 羧 酸 酯
11.1A Structure of the carbonyl group 120 1. C-sp* hybridization 2. The bond angles is 120 1200 3. It is a trigonal planar structure 4. The carbon-oxygen double bond 120° consists of sigma-a bond and a pi-bond 120 120 120 Polarization of the T-bond Resonance structures
11.1A Structure of the carbonyl group O 120 o 120 o 120 o 1. C-sp 2 hybridization 2. The bond angles is 120 o . 3. It is a trigonal planar structure 4. The carbon-oxygen double bond consists of sigma-a bond and a pi-bond O 120 o 120 o 120 o O O O O + − + O- Polarization of the - bond Resonance structures
11.1B Reaction of carbonyl compounds with nucleophiles NU 8+8 u Polarization of the T-bond TH Reduction OH [OJ Oxidation
11.1B Reaction of carbonyl compounds with nucleophiles O + − Polarization of the - bond :Nu + - O - Nu O OH [ H ] Reduction [ O ] Oxidation
NabHg or lianG IH]」 Reduction OH IO Oxidation KMno R NaBH4 or LiAlH4 ROH o H RCH,OH [H Reduction nucleophilic addition h
O OH [ H ] Reduction [ O ] Oxidation NaBH4 or LiAlH4 KMnO4 R H O R H O- [ H ] Reduction NaBH4 or LiAlH4 + H - H ROH RCH2OH nucleophilic addition
11.2 Oxidation Reduction reactions in organic chemistry Reduction of an organic molecule usually corresponds to increasing its hydrogen content or to decreasing its oxygen content. oxygen content decreases oxygen content decreases IHI H R—cH2OH OH R Reduction Reduction Carboxylic acid Aldehy Aldehyde Alcohol oxvgen content decreases THI R—cH2OH R——cH3 Reduction Alcohol Alkanes
11.2 Oxidation-Reduction reactions in organic chemistry Reduction of an organic molecule usually corresponds to increasing its hydrogen content or to decreasing its oxygen content. R O OH [ H ] Reduction R O H Carboxylic acid Aldehyde oxygen content decreases R O H [ H ] Reduction R CH2OH Aldehyde Alcohol oxygen content decreases [ H ] Reduction R CH3 Alcohol Alkanes oxygen content decreases R CH2OH