Ch14su09

Ch14su09 - Organic Chemistry II with Prof. Burke Lecture...

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Unformatted text preview: Organic Chemistry II with Prof. Burke Lecture Notes http://camchem.rutgers.edu/~burke Email burke@camden.rutgers.edu Room Sci 114B Office Hours Half-hour before and after each lecture or by appt. Text (a) Organic Chemistry Wade, 4 th ,5 th , or 6 th Edition (b) Solution Manual to Organic Chemistry (organic model kit) Do the chapter examples in the book Learn as you go along Aim for understanding, not memorization Use Chemistry Department (Burke, Fazen, Roche) exams as a guide. 3f740ac66f5514ef503a4cfbfd0fbdfc34254a57.doc Page1 Ethers and Epoxides Ethers are a class of compound of the general formula R-O-R. R and R can be alkyl or aryl. Structure Ethers can be thought of as alkyl analogues of water. Uses Since ethers are relatively unreactive and are somewhat polar (due to the lone pairs on the oxygen), they are commonly used as solvents for organic reactions. (Diethyl ether and THF, the Grignard reaction). Ethers will often form complexes with molecules that have vacant orbitals, enabling unstable molecules to be used as reagents. E.g. Hydroboration uses BH 3 .THF Crown ethers are macrocyclic ethers, which help to solvate metal cations, and thus allow inorganic salts to dissolve in organic solvents. 3f740ac66f5514ef503a4cfbfd0fbdfc34254a57.doc Page2 H O H R O R B H B H H H H H O 2 O B H H H + _ 2 18-Crown-6 is the ideal size to incorporate a potassium ion, and allows organic solutions of ionic potassium salts to be prepared (purple benzene, KMnO 4 ). 3f740ac66f5514ef503a4cfbfd0fbdfc34254a57.doc Page3 O O O O O O K + 18-Crown-6 Ethers differentially solvate cations and anions. The cations are strongly bonded to the lone pairs of the ether, leaving the anions more available for attack (S N 2, KMnO 4 , ) Nomenclature of ethers Common names trivial names of ethers add the suffix ether after naming the groups on either side of the oxygen, e.g. methyl ethyl ether H 3 COCH 2 CH 3 . IUPAC names ethers by taking the more complex alkyl group the root name, and naming the remaining part as an alkoxy group....
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Ch14su09 - Organic Chemistry II with Prof. Burke Lecture...

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