Presentation on theme: "Chapter 11. Alcohols from carbonyl compounds (由羰基化合物制醇）."— Presentation transcript:
1Chapter 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 IntroductionCarbonyl (羰基）compounds are a broad group of compoundsthat includes aldehydes, ketones, carboxylic acids, and esters.
10The mechanism for the reduction of a ketone by sodium borohydride and Lithium aluminum hydride Sodium borohydride (NaBH4) is a milder reducing agentthan lithium aluminum hydride (LiAlH4). Lithium aluminumhydride will reduce acids. Esters, aldehydes, and ketones;but sodium borohydride will reduce only aldehydes and ketones.
11Primary alcohols can be oxidized to aldehydes and carboxylic acids. 11.4 Oxidation of alcoholsPrimary alcohols can be oxidized to aldehydes and carboxylic acids.
1511.4E A Chemical test for primary and secondary alcohols
1611.5 Organometallic compounds （有机金属化合物） Compounds that contain carbon-metal bonds are called organometallic compounds. It include Carbon-lead, carbon-tin, carbon-thallium, carbon-mercury, carbon-lithium and carbon-magnesium bonds.
1811.6 Preparation of organolithium and organomagnesium compounds 11.6A Organolithium compounds (有机锂化合物）Organolithium compounds are often prepared by the reaction of organic halides with lithium metal.
1911.6B Grignard reagents （格利雅试剂）; Organomagnesium halides were discovered by the French chemist Victor Grignard in Grignard received the Nobel Prize for his discovery in 1912, and organomagnesium halides are now called Grignard reagents in his honor. Grignard reagents have great use in organic synthesis.
20Grignard reagents are usually prepared by the reaction of an organic halides and magnesium metal in an ether solvent
21A Grignard reagent forms a complex with its ether solvent; the structure of the complex can be represented as follows:
2211.7 Reactions of organolithium and organomagnesium compounds 11.7A Reactions with compounds containing acidic hydrogen atoms
23Grignard reagents and organolithium compounds abstract protons that are much less acidic than those of water and alcohols. They react with the terminal hydrogen atoms of 1-alkynes.
2411.7B Reaction of Grignard reagents with oxiranes (环氧乙烷与格利雅试剂反应） 在合成上增加两个碳原子伯醇