\"Nicotine in cigar smoke (pH 8.5) is much more readily absorped through the muc

Question

"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.

Explanation / Answer

A)

iii) pH of greater than 8 (approximately around 8.5)

B)

The pH of the aqueous fraction of cigar smoke is generally around 8.5, ... cigarettesmoke is poorly absorped through the ... Nicotine seemed to be more readily ...

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