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Chapter 11: 45cE (page 350)
How might you prepare each of the following molecules using a nucleophilic substitution reaction at some step?
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Methyl esters () undergo a cleavage reaction to yield carboxylate ions plus iodomethane on heating with LiI in dimethylformamide:
The following evidence has been obtained: (1) The reaction occurs much faster in DMF than in ethanol. (2) The corresponding ethyl ester () cleaves approximately 10 times more slowly than the methyl ester. Propose a mechanism for the reaction. What other kinds of experimental evidence could you gather to support your hypothesis?
Question: There are eight diastereomers of 1,2,3,4,5,6-hexachlorocyclohexane. Draw each in its more stable chair conformation. One isomer loses HCl in an E2 reaction nearly 1000 times more slowly than the others. Which isomer reacts so slowly, and why?
The following Walden cycle has been carried out. Explain the results, and indicate where Walden inversion occurs.
Organic solvents like benzene, ether, and chloroform are neither protic nor strongly polar. What effect would you expect these solvents to have on the reactivity of a nucleophile in reactions?
Treatment of 1-bromo-2-deuterio-2-phenylethane with strong base leads to a mixture of deuterated and nondeuterated phenylethylenes in an approximately 7;1 ratio. Explain
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