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Salicylaldehyde reacts with diethyl zinc in a 1:1 ratio to form compound A according to the following scheme: OH O +Et₂Zn gas On cooling, compound B crystallises from solution, and half an equivalent of diethyl zinc is found to have reformed in solution. B + 0.5 Et₂Zn d. Identify A, B, and the gas. [3 marks] e. By what process does A transform to B? Sketch a plausible intermediate. [2 marks] f. A reacts cleanly with anhydrous HCI to release a gas and form compound C. Identify C, and explain why this is the sole product. [2 marks] Question continues on next page g. A reacts cleanly with Me SiCI to form compound D, with molecular weight 194, a colourless crystalline solid, E, and reform some Et Zn. Identify D and E using the available data, and explain why this is the sole product. [4 marks]

Salicylaldehyde reacts with diethyl zinc in a 1:1 ratio to form compound A according to the following scheme: OH O +Et₂Zn gas On cooling, compound B crystallises from solution, and half an equivalent of diethyl zinc is found to have reformed in solution. B + 0.5 Et₂Zn d. Identify A, B, and the gas. [3 marks] e. By what process does A transform to B? Sketch a plausible intermediate. [2 marks] f. A reacts cleanly with anhydrous HCI to release a gas and form compound C. Identify C, and explain why this is the sole product. [2 marks] Question continues on next page g. A reacts cleanly with Me SiCI to form compound D, with molecular weight 194, a colourless crystalline solid, E, and reform some Et Zn. Identify D and E using the available data, and explain why this is the sole product. [4 marks]