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"Nicotine in cigar smoke (pH 8.5) is much more readily absorped through the mucous membranes of the mouth than is nicotine in cigarette smoke (pH 5.3)..." [pKa for the pyridine NH (6-membered ring) is about 3, pyrrolidine NH pKa is about 8].

A. Use the Henderson-Hasselbalch and the definition of conjugate base/acid to determine the charge on most of the nicotine molecules or ions in the following pH ranges.

i. pH less than 3

ii. pH of 3 to 8

iii. pH of greater than 8

B. Use your answers in a. to explain the statement.

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