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Bruice 8th EditionCh.10 - Reactions of Alcohols, Ethers, Epoxides, Amines, and Sulfur-Containing CompoundsProblem 90
Which of the following reactions occurs more rapidly?
Problem 91b
Propose a mechanism for each of the following reactions:
b.
Problem 91c
Propose a mechanism for each of the following reactions:
c.
Problem 92
A vicinal diol has OH groups on adjacent carbons. The dehydration of a vicinal diol is accompanied by a rearrangement called the pinacol rearrangement. Propose a mechanism for this reaction.
Problem 93a
Although 2-methyl-1,2-propanediol is an unsymmetrical vicinal diol, only one product is obtained when it is dehydrated in an acidic solution.
a. What is this product?
Problem 93b
Although 2-methyl-1,2-propanediol is an unsymmetrical vicinal diol, only one product is obtained when it is dehydrated in an acidic solution.
b. Why is only one product obtained?
Problem 94
What product is obtained when the following vicinal diol is heated in an acidic solution?
Problem 95
Two stereoisomers are obtained from the reaction of cyclopentene oxide and dimethylamine. The R,R-isomer is used in the manufacture of eclanamine, an antidepressant. What other isomer is obtained?
Problem 96a
Propose a mechanism for each of the following reactions:
a.
Problem 96b
Propose a mechanism for each of the following reactions:
b.
Problem 97b
Triethylenemelamine (TEM) is an antitumor agent. Its activity is due to its ability to cross-link DNA.
b. Explain why it can cross-link DNA.
