Solved Exercises Integrating the Concepts

In the first five chapters, we examined the most basic ideas of organic chemistry. We applied principles of general chemistry, such as orbital theory, thermodynamics, and kinetics, to organic molecules. We also introduced topics of particular relevance to organic chemistry, such as isomerism and stereochemistry. The properties and reactions of alkanes gave us an opportunity to observe many of these basic principles in action. 

Replace sodium ethoxide with sodium ethanethiolate, NaSCH2CH3. 

Table 6-4 tells us that fluoride is a stronger base than bromide and, therefore, a poorer leaving group. The reaction would stiU take place but would be very much slower. (The actual rate decrease is of the order of 10. ) 

The carbon containing the leaving gronp in bromomethane is less stericaUy hindered than that in bromoethane, so the rate of reaction wonld increase (Section 6-10). The product of the reaction would be CH3OCH2CH3, methoxyethane. 

Conversion from a protic, hydrogen-bonding solvent to a polar, aprotic one accelerates the reaction enormously by reducing solvation of the negatively charged oxygen atom (compare Table 6-6). See Problem 57 for a similar exercise. 

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