Alicyclics - Alicyclics Aliphatic compounds containing...

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Unformatted text preview: Alicyclics Aliphatic compounds containing rings, cycloalkanes, cycloalkyl halides, cycloalkyl alcohols, cyclic ethers, cycloalkenes, cycloalkadienes, etc. Cycloalkanes H 2 C H 2 C CH 2 H 2 C H 2 C CH 2 CH 2 H 2 C H 2 C C H 2 CH 2 H 2 C H 2 C H 2 C C H 2 CH 2 CH 2 H 2 C cyclopropane cyclobutane cyclopentane cyclohexane CH 3 Br Br Br Br CH 3 H 3 C methylcyclopentane 1,1-dimethylcyclobutane trans-1,2-dibromocyclohexane Br Br H O H O HO OH HO OH cis- 1,2-cyclohexanediol cyclopentene 3-methylcyclohexene 1,3-cyclobutadiene 1 2 3 4 5 6 cycloalkenes OH O CH 2 CH 3 cyclohexanol ethyl cyclopentyl ether cyclohexyl alcohol Cycloalkanes, syntheses : A. Modification of a ring compound: 1. reduction of cycloalkene 2. reduction of cyclic halide a) hydrolysis of Grignard reagent b) active metal & acid 3. Corey House B. Ring closures A. Modification of a cyclic compound: Br Br H 2 , Ni Sn, HCl Mg; then H 2 O Br Li 2 CuLi Li CuI + CH 3 CH 2-Br CH 2 CH 3 must be 1 o Corey-House A. ring closures CH 2 =CH 2 + CH 2 CO, hv Br-CH 2 CH 2 CH 2 CH 2 CH 2-Br + Zn etc. cycloalkanes, reactions: 1. halogenation 2. combustion 3. cracking 4. exceptions Cl Cl 2 , heat + HCl exceptions: H 2 , Ni, 80 o CH 3 CH 2 CH 3 Cl 2 , FeCl 3 Cl-CH 2 CH 2 CH 2-Cl H 2 O, H + CH 3 CH 2 CH 2-OH conc. H 2 SO 4 CH 3 CH 2 CH 2-OSO 3 H HI CH 3 CH 2 CH 2-I exceptions (cont.) + H 2 , Ni, 200 o CH 3 CH 2 CH 2 CH 3 ?????????? internal bond deviation heat of angles from 109.5 combustion 60 o-49.5 o 166.6 90 o-19.5 o 164.0 108 o-1.5 o 158.7 Cyclopropane undergoes addition reactions that other...
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This note was uploaded on 11/02/2010 for the course CHEM 51LA 56555 taught by Professor Guan during the Spring '10 term at UC Irvine.

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Alicyclics - Alicyclics Aliphatic compounds containing...

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