Ch14 - Organic Chemistry II with Dr Roche Lecture Notes...

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Organic Chemistry II with Dr Roche Lecture Notes http://crab.rutgers.edu/~alroche Email alroche@crab.rutgers.edu Room Sci 311 (labs: Sci 328F/309/304A/318/319) Phone 225-6166 Text (a) “Organic Chemistry” Wade, 4 th Edition (b) Solution Manual to Organic Chemistry, 4 th Ed (organic model kit) Do the problems in the book Learn as you go along Aim for understanding, not memorization 68a0577275755b79933f2bf4920c36e8626942ef.doc Page1
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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 strongly 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. 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). 68a0577275755b79933f2bf4920c36e8626942ef.doc Page2 H O H R O R B H B H H H H H O 2 O B H H H + _ 2 O O O O O O K + 18-Crown-6
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Nomenclature of ethers Common names of ethers add the suffix ether after naming the groups on either side of the oxygen. IUPAC names ethers by taking the more complex alkyl group the root name, and naming the remaining part as an alkoxy group. E.g. Cyclic Ethers Naming these heterocyclic compounds depends on the ring size and number of oxygens. (It can be confusing at first…) Epoxides These 3 membered rings are named using the term epoxy as a substituent. (cis refers to the substituents, not the epoxide which must
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Ch14 - Organic Chemistry II with Dr Roche Lecture Notes...

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