Chapter 18: Q16P (page 588)
Name the following compounds:

Short Answer
Answer
- 2-Butanethiol
- 2,2,6-Trimethyl-4-heptanethiol
- 2-Cyclopentene-1-thiol
- Ethyl isopropyl sulfide
- o-(Dimethylthio)benzene
- 3-(Ethylthio)cyclohexanone
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Chapter 18: Q16P (page 588)
Name the following compounds:

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

Predict the product(s) and provide the mechanism for each two-step
process below.




How would you prepare the following ethers using a Williamson synthesis?
The alkoxymercuration of alkenes involves the formation of an organomercury intermediate (I), which is reduced with NaBH4 to give an etherproduct. For each reaction below, predict the ether product and provide the mechanism formation.
(a)

(b)

(c)

Treatment of trans-2-chlorocyclohexanol with NaOH yields 1,2-epoxycyclohexane,but reaction of the cis isomer under the same conditionsyields cyclohexanone. Propose mechanisms for both reactions, andexplain why the different results are obtained.

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