Thiols and Thiolates R-SH about same acidity as phenols. CH3CH-SH NaOH>CH3CH2-S Na"HOH Thiolates are better nucleophiles,weaker bases,than alkoxides. Br SCH: CH3一C-CH3 CH3S CH3-C-CH3 CHOH H H 2°halide Substitution product = Chapter 14 22Chapter 14 22 Thiols and Thiolates • R-SH about same acidity as phenols. CH3 CH2 SH + NaOH Na + CH3 CH2 S + HOH _ • Thiolates are better nucleophiles, weaker bases, than alkoxides. CH3 C CH3 H Br CH3 OH CH3 S _ CH3 C CH3 H SCH3 2 halide Substitution product =>