(Nucleophillic substitution experiment): For part C of the experiment, what is t

Question

(Nucleophillic substitution experiment): For part C of the experiment, what is the purpose of adding acetone? Predict what would happen if you omitted the acetone in the experimental procedure?

Part Synthesis of triphenylmethanol Place 0.5 g of triphenylmethyl bromide in a 100 mL round bottom flask with magnetic stirrer. Add 10 mL of acetone and stir until dissolved. Next add 20 mL of water and stir for 10 minutes. Cover the bottom of a 100 mL beaker with ice and pour the entire reaction mixture over the ice, including the stir bar. Continue to stir in the beaker until the ice has melted. Vacuum filter the solid and rinse with 5 mL of cold water and allow it to dry on the vacuum line for 5 minutes. Recrystallize your product from isopropanol (review technique 11 in your lab manual). Allow your product to dry over the vacuum for a additional 5 minutes. Weigh the final purified product and determine the percent yield. Take an infrared spectrum of your product using an ATR attachment and determine its melting range.

Explanation / Answer

Acetone will act as solvent, as triphenylmethyl bromide is an organic compound which will be soluble in organic solvent not in polar solvent like water. The reaction involving nucleophillic substitution of bromide with hydroxyl group can only be acheived if the compound is available for attack by OH- present in water. As acetone is miscible with water, first dissolution of organic compound occurs and then addition of water caused the reaction to occur.

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