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
Which is a stronger base, water or formate? (Formate is the conjugate base of formic acid.)
Identify the HOMO and the LUMO in the water-formic acid reaction Specify both the orbital and
the molecule that contains it.
Circle the more acidic molecule in each of the following pairs. (12 pts)
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)
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