Chapter 18: Q25-E (page 594)
Predict the product(s) and provide the mechanism for each two-step
process below.




Short Answer
a.

b.

c.

d.

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Chapter 18: Q25-E (page 594)
Predict the product(s) and provide the mechanism for each two-step
process below.




a.

b.

c.

d.

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How would you synthesize anethole (Problem 18-54) from phenol?
15-Crown-5 and 12-crown-4 ethers complex Na+ and Li+, respectively. Make models of these crown ethers, and compare the sizes of the cavities.
The 1H NMR spectrum shown is that of a cyclic ether with the formula C4H8O. Propose a structure.

Imagine that you have created (2R, 3R)-2,3-epoxy-3-methylpentane with aqueous acid to carry out a ring opening reaction.

The Zeisel method is an old analytical procedure for determining the number of methoxyl groups in a compound. A weighed amount of the compound is heated with concentrated HI, ether cleavage occurs, and the iodomethane product is distilled off and passed into an alcohol solution of , where it reacts to form a precipitate of silver iodide. The AgI is then collected and weighed, and the percentage of methoxyl groups in the sample is thereby determined. For example, 1.06 g of vanillin, the material responsible for the characteristic odour of vanilla, yields 1.60 g of AgI. If vanillin has a molecular weight of 152, how many methoxyl groups does it contain?
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