16%20Ch10 - CHAPTER 10 Reactions of Alcohols, Amines,...

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303 CHAPTER 10 Reactions of Alcohols, Amines, Ethers, Epoxides, and Sulfur-Containing Compounds • Organometallic Compounds Important Terms alcohol an organic compound with an OH functional group (ROH). alkaloid a natural product with a nitrogen heteroatom found in the leaves, bark, or seeds of plants. alkyl tosylate an ester of para- toluenesulfonic acid. alkyl triflate an ester of trifluoromethanesulfonic acid. antibiotic a compound that interferes with the growth of a microorganism. arene oxide an aromatic compound that has had one of its double bonds converted to an epoxide. coupling reaction a reaction that joins two carbon-hydrogen containing groups. crown ether a cyclic molecule that possesses several ether linkages. crown-guest complex the complex formed when a crown ether binds a substrate. dehydration loss of water. ether a compound containing an oxygen bonded to two carbons (ROR). Gilman reagent a dialkylcopper reagent used to replace a halogen with an alkyl group. Grignard reagent the compound that results when magnesium is inserted between the carbon and halogen of an alkyl halide (RMgBr, RMgCl). Heck reaction couples an aryl, benzyl, or vinyl halide or triflate with an alkene. inclusion compound a compound that specifically binds a metal ion or an organic molecule. mercapto group an SH group. molecular recognition the recognition of one molecule by another as a result of specific interactions. organocuprate (R) 2 CuLi; prepared by treating an organolithium reagent with cuprous iodide. organolithium compound RLi; prepared by adding lithium to an alkyl halide. organomagnesium RMgBr; prepared by adding an alkyl halide to magnesium shavings. compound
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304 Chapter 10 organometallic compound a compound with a carbon-metal bond. phase-transfer catalyst a compound that carries a polar reagent into a nonpolar phase. Stille reaction couples an aryl, benzyl, or vinyl halide or triflate with a stannane. sulfide (thioether) the sulfur analog of an ether (RSR). sulfonate ester the ester of a sulfonic acid (RSO 2 OR). sulfonium salt (R) 3 S + X Suzuki reaction couples an aryl, benzyl, or vinyl halide or triflate with an organoborane. thioether (sulfide) the sulfur analog of an ether (RSR). thiol (mercaptan) the sulfur analog of an alcohol (RSH). transmetallation metal exchange. vicinal diol (vicinal glycol) a compound with OH groups bonded to adjacent carbons.
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Chapter 10 305 Solutions to Problems 1. They no longer have a lone pair of electrons. 2. a. Solved in the text. b. The conjugate acid of the leaving group of CH 3 OH 2 + is H 3 O + ; its p K a is = –1.7. The conjugate acid of the leaving group of CH 3 OH is H 2 O; its p K a is = 15.5. Because H 3 O + is a much stronger acid than H 2 O, H 3 O + is the weaker base and the better leaving group. Thus, CH 3 OH 2 + is more reactive than CH 3 OH.
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16%20Ch10 - CHAPTER 10 Reactions of Alcohols, Amines,...

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