Question

Draw a pathway for the reaction of phenylboronic acid with 4-iodophenol to obtain 4-phenylphenol in the form of a catalytic cycle. EXPLAIN and STATE all complexes formed in EACH STEP by their electron counts (count how many e^- are there, e.g. 18 e^- or 16 e^- etc.), formal oxidation states and all the reactions with mechanistic labels (i.e. oxidative addition, reductive elimination, etc.) (note the amount of base used). Be sure to EXPLAIN the catalytic cycle as to what happens in each step. The experimental procedure that was followed in the experiment is also shown below if it is needed in answering the question above.

Preheat a magnetic stirrer/hotplate to about 150 °C. Weigh out the following reagents (using an analytical balance) and add them to a 50 mL Quickfit conical flask: phenylboronic acid (0.122 g), potassium carbonate (0.415 g) and 4-iodophenol (0.220 g). Add water (10 mL) and a small magnetic stirrer bar You are supplied with a sample of 10% Pd on charcoal in a small sample vial. Add water (1 mL) to make a suspension. Transfer this suspension to your flask with a Pasteur pipette. Clamp the flask on the hotplate and place a reflux condenser on the flask. Boil the mixture under reflux with vigorous stirring for 30 minutes (it must actually boil for this entire time) Remove the flask from the hotplate and allow it to cool to room temperature (ice may be used to cool it more rapidly). Add hydrochloric acid (2 M) to the flask with stirring until the mixture is acidic to indicator paper. Collect the crude product (which will still contain the palladium on charcoal) using a Buchner funnel, and wash it with water (10 mL) Place the collected solid in a 50 mL conical flask and add methanol (10 mL) to dissolve the product. Use some of this methanol to wash the filter paper to transfer any solid sticking to the filter paper. Filter the solution through a Pasteur pipette containing a

Answer 1