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1. Draw a mechanism for the reaction of water with formic acid. Formic acid is a carboxylic acid with the formula HCOOH and a pK, of 3.76. Draw the products of this reaction showing all lone pairs of electrons and non-zero formal charges. Include all necessary curved arrows in your mechanism Indicate which side of the reaction is favored at equilibrium and explain your answer. The pK, of hydronium ion, H2O*, is -1.7. (18 pts) Side favored: (circle one) Reactants Products Explanation Which is a stronger base, water or formate? (Formate is the conjugate base of formic acid.) Water Formate Identify the HOMO and the LUMO in the water-formic acid reaction Specify both the orbital and the molecule that contains it. HOMO: LUMO: 2. Circle the more acidic molecule in each of the following pairs. (12 pts) or OH 'OH NH2 OH or H2S or H2O 3. Cyanic acid, HOCN, and isocyanic acid, OCNH, have the same pK, (3.5). Using an argument supported by appropriate chemical structures, explain why. Your structures should include all nonzero formal charges and lone pairs of electrons Hint: What approach did we use in lecture to compare acid strengths? (10 pts) IOCIN: 0=C=N-H .. ** cyanic acid isocyanic acid

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