Dolbier HW Solutions 314

Dolbier HW Solutions 314 - CH 3 Br Methyl bromide 1 CH 3 CH...

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16.23 ( a ) There are three methyl-substituted thianes, two of which are chiral. ( b ) The locants in the name indicate the positions of the sulfur atoms in 1,4-dithiane and 1,3,5- trithiane. ( c ) Disul f des possess two adjacent sulfur atoms. 1,2-Dithiane is a disul f de. ( d ) Two chair conformations of the sulfoxide derived from thiane are possible; the oxygen atom may be either equatorial or axial. 16.24 Intramolecular hydrogen bonding between the hydroxyl group and the ring oxygens is possible when the hydroxyl group is axial but not when it is equatorial. 16.25 The ethers that are to be prepared are First examine the preparation of each ether by the Williamson method. Methyl propyl ether can be prepared in two ways:
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Unformatted text preview: CH 3 Br Methyl bromide 1 CH 3 CH 2 CH 2 ONa Sodium propoxide CH 3 OCH 2 CH 2 CH 3 Methyl propyl ether CH 3 ONa Sodium methoxide 1 CH 3 CH 2 CH 2 Br 1-Bromopropane CH 3 OCH 2 CH 2 CH 3 Methyl propyl ether and CH 3 OCH 2 CH 2 CH 3 Methyl propyl ether CH 3 OCH(CH 3 ) 2 Isopropyl methyl ether CH 3 CH 2 OCH 2 CH 3 Diethyl ether O O HO Less stable conformation; no intramolecular hydrogen bonding O O O H More stable conformation; stabilized by hydrogen bonding S O 2 S O 1 2 1 S S 1,2-Dithiane S S 1,4-Dithiane S S S 1,3,5-Trithiane S CH 3 2-Methylthiane (chiral) S CH 3 3-Methylthiane (chiral) S CH 3 4-Methylthiane (achiral) 408 ETHERS, EPOXIDES, AND SULFIDES...
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