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Dr. Glaser's "Chemistry is in the News"
To Accompany Bruice, Organic Chemistry, 3/e.
Chapter 15. Reactions of Substituted Benzenes.


For each of the following questions, please refer to the following article:
BIG TOBACCO SEEKS CIGARETTE OF THE FUTURE: INSIDE WASHINGTON
by Monroe W. Karmin (Blomberg News, June 25, 1997)


Editorial Comments

Searching the dictionary of Encyclopaedia BRITANNICA online for "oxymoron" returns the definition:

ox.y.mo.ron n, pl -mo.ra [LGk oxymoron, fr. neut. of oxymoros pointedly foolish, fr. Gk oxys sharp, keen + moros foolish] (1657): a combination of contradictory or incongruous words (as cruel kindness) -- ox.y.mo.ron.ic adj -- ox.y.mo.ron.i.cal.ly adv

If you expand the search to "article" searches, then you can find examples of oxymorons. "Liquid crystal" certainly is an excellent example. Liquid crystals, their very name an oxymoron, blend structures and properties of the normally disparate liquid and crystalline solid states.

"Oxymoron" differs from "paradox". Both terms describe apparently self-contradictory statements but in the case of the paradox the self-contradictory nature of the statement is revealed only after careful scrutiny.

With this linguistic excursion, you are now all set to see it very clearly: "Safe cigarette" is an oxymoron. The term is obviously foolish and absurd.


Pertinent Text References
Chapter 15. Reactions of Substituted Benzenes
Chapter 15. Box on "Nitrosamines and Cancer".



Questions

Question 1: Nitrosamines are carcinogenic because they undergo decomposition reactions that lead to diazonium ions which are the active carcinogens. Using the nitrosamine of aniline, write down the mechanisms for the conversion of the nitrosamine to benzenediazonium ion.

Answer 1: See Bruice 3/e, Chapter 15.12.



Question 2: Many nitrosamines are formed in vivo when nitrous acid comes in contact with amines. Show how nitrous acid is formed from nitrite salts (e.g. sodium nitrite) and how the nitrosonium ion is formed from nitrous acid.

Answer 2: See Bruice 3/e, Chapter 15.12.



Question 3: Nitrosamines are only one class of carcinogenic compounds contained in cigarette smoke. Give the names of at least three other classes of compounds that also are carcinogenic and occur in tobacco smoke.

Answer 3: Surf the web.



Question 4: Benzenediazonium ion are the best substrates for nucleophilic aromatic substitution. Give reagents and products for three such nucleophilic aromatic substitutions of benzenediazonium chloride.

Answer 4: Bruice, 3/e, Chapter 15.10.



Chemistry and Society.
Question 5: Take a look a the website on American Temperance and Prohibition by the Department of History at the Ohio State University. Compare and contrast the events before, during and after prohibition with the current events concerning the use of tobacco. To start your discussion, consider the quote "Prohibition in the United States was a measure designed to reduce drinking by eliminating the businesses that manufactured, distributed, and sold alcoholic beverages" and recognize that it did not work and why it did not work.