1559T_ch22_389-40811/7/0515:40Page399 EQA Solutions to Problems.399 50.(a)5-Bromo-2-chlorophenol;(b)4-(hydroxymethylphenol (e)2.4-dihydroxybenzenesulfonic acid:(d)2-phenoxyphenol: (e)2-methylthio-2.5-cyclohexadiene-1.4-dione OH OCH2CH=CH2 CH,CH=CH, 51.(a)CH-CHCH OCH2CH=CH2 CH 上29 (b)Step-by-ste ⊕ The thiol is readily oxidized,so one likely reaction i Redox- OH Another possibility is OH Conjugate addition 50. (a) 5-Bromo-2-chlorophenol; (b) 4-(hydroxymethyl)phenol; (c) 2,4-dihydroxybenzenesulfonic acid; (d) 2-phenoxyphenol; (e) 2-methylthio-2,5-cyclohexadiene-1,4-dione 51. (a) (b) Step-by-step: (c) (d) (e) The thiol is readily oxidized, so one likely reaction is Another possibility is SCH2CH3 Conjugate addition OH OH Redox CH3CH2SSCH2CH3 OH OH  H3C CH3 O O O O Cl Cl Cl Cl NaOH,  Aldol O O CH3 O CH3 O 1. O3, CH2Cl2  2. Zn, H2O CH3 O OH OH OCH2CH CH2 OCH2CH CH2 CH2 CHCH2 CH2CH CH2 via double Claisen rearrangement of Solutions to Problems • 399 1559T_ch22_389-408 11/7/05 15:40 Page 399