Due 9/18/14 at the beginning of class The equation below shows the equilibrium e

Question

Due 9/18/14 at the beginning of class The equation below shows the equilibrium equation for two constitutional isomers with different pKa values. You can determine isomer is more acidic by analyzing the structures and considering the factors that affect acidity. After identifying which one is more acidic indicate which side the acid-base reaction favors using equilibrium arrows with a larger arrow to indicate the favored side. Provide a brief explanation describing why one isomer is more acidic than the other For each of the following groups of molecules rank the compounds from the weakest to strongest acid (1 = weakest acid: 4 = strongest acid).

Explanation / Answer

THE EQUIBRIUM WILL BE SHIFTED TO THE RIGHT SIDE BECAUSE P-NITRO PHENOL IS MORE ACIDIC AND THUS WILL PREFER TO REMAIN AS AN IONIC FORM.

A               3 < 1 < 4 <2

B     1 < 4 < 2 < 3

C    1 < 3 < 2 < 4

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