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Br 1.6 points total) 24.6-Tribromophenolis a wood preservative and intermediate in the OH preparation of flame-retarding brominated compounds (M-330.80 g mor; T. 95.S°C T=2869). You're dealing with a soll contaminated with this compound (call "TSP") and need to know its aqueous solubility at 25*C, for which you find a value of Cw=104 M, but you recognize that the solubility may be affected by the pH of the soil pore water. You look up the pk for TBP and find two values, 6.18 and 6.90, both for 25*C, which suggests that one of the values was not measured correctly. You decide to check the pk with an estimate Br 3a (1 point write the proton exchange reaction for 24,6-tribromophenol (TP) showing its structure on both the reactant and product side of the reaction 36. (3 points) What is the estimated pk of 24,6-tribromophenol (TP)? * 246-Tribromophenol is also a naturally occurring flavor component of seafood 3c (2 points) At what pH would TP be more soluble in water, pH 5 or pH 8? Calculate the fractions of TBP In the protonated for at pH5 and pH 8, and use these fractions to explain the difference in solubility in about 50 words or fewer. Note: Calculations of the solubilities are not requested just the fractions in the protonated form

Br 3. (6 points total) 2,4,6-Tribromophenol is a wood preservative and intermediate in the OH preparation of flame-retarding brominated compounds* (M= 330.80 g mol-'; T = 95.5°C; To = 286°C). You're dealing with a soil contaminated with this compound (call it "TBP“) and need Br to know its aqueous solubility at 25°C, for which you find a value of C = 10-368 M, but you recognize that the solubility may be affected by the pH of the soil pore water. You look up the pK, for TBP and find two values, 6.18 and 6.90, both for 25°C, which suggests that one of the values was not measured correctly. You decide to check the pk with an estimate. Br 3a. (1 point) Write the proton exchange reaction for 2,4,6-tribromophenol (TBP) showing its structure on both the reactant and product side of the reaction. 3b. (3 points) What is the estimated pk of 2,4,6-tribromophenol (TBP)?

* 2,4,6-Tribromophenol is also a naturally-occurring flavor component of seafood! 3c. (2 points) At what pH would TBP be more soluble in water, pH 5 or pH 8? Calculate the fractions of TBP in the protonated form at pH 5 and pH 8, and use these fractions to explain the difference in solubility in about 50 words or fewer. Note: Calculations of the solubilities are not requested - just the fractions in the protonated form