Dolbier HW Solutions 261

Dolbier HW Solutions 261 - e ) CH 2 I Benzyl iodide CH 2 Br...

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11.6 ( b ) Only the benzylic hydrogen is replaced by bromine in the reaction of 4-methyl-3-nitroanisole with N -bromosuccinimide. 11.7 The molecular formula of the product is C 12 H 14 O 4 . Since it contains four oxygens, the product must have two @ CO 2 H groups. None of the hydrogens of a tert -butyl substituent on a benzene ring is benzylic, and so this group is inert to oxidation. Only the benzylic methyl groups of 4- tert -butyl-1,2- dimethylbenzene are susceptible to oxidation; therefore, the product is 4- tert -butylbenzene-1,2- dicarboxylic acid. 11.8 Each of these reactions involves nucleophilic substitution of the S N 2 type at the benzylic position of benzyl bromide. ( b ) ( c ) ( d ) (
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Unformatted text preview: e ) CH 2 I Benzyl iodide CH 2 Br Benzyl bromide I 2 Iodide ion CH 2 SH Phenylmethanethiol CH 2 Br Benzyl bromide HS 2 Hydrogen sulfide ion N 2 N 1 CH 2 N Benzyl azide CH 2 Br Benzyl bromide N 2 N 2 N 1 Azide ion CH 2 OC(CH 3 ) 3 Benzyl tert-butyl ether CH 2 Br Benzyl bromide (CH 3 ) 3 CO 2 tert-Butoxide ion CH 3 CH 3 (CH 3 ) 3 C Susceptible to oxidation Not benzylic hydrogens; not readily oxidized Na 2 Cr 2 O 7 H 2 O, H 2 SO 4 , heat CO 2 H CO 2 H (CH 3 ) 3 C 4-tert-Butylbenzene-1,2-dicarboxylic acid CH 2 Br OCH 3 NO 2 CH 3 OCH 3 NO 2 Only these hydrogens are benzylic. NBS 80 8 C, peroxides ARENES AND AROMATICITY 255...
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This note was uploaded on 09/26/2011 for the course CHM 2210 taught by Professor Reynolds during the Fall '01 term at University of Florida.

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