Dolbier HW Solutions 596

Dolbier HW Solutions 596 - 690 PHENOLS 24.19 The three...

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24.19 The three parts of this problem make up the series of steps by which o -bromophenol is prepared. ( a ) Because direct bromination of phenol yields both o -bromophenol and p -bromophenol, it is essential that the para position be blocked prior to the bromination step. In practice, what is done is to disulfonate phenol, which blocks the para and one of the ortho positions. ( b ) Bromination then can be accomplished cleanly at the open position ortho to the hydroxyl group. ( c ) After bromination the sulfonic acid groups are removed by acid-catalyzed hydrolysis. 24.20 Nitration of 3,5-dimethylphenol gives a mixture of the 2-nitro and 4-nitro derivatives.
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