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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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.

Draw structures corresponding to the following IUPAC names:
(a)Ethyl 1-ethylpropyl ether (b)Di(p-chlorophenyl) ether
(c)3,4-Dimethoxybenzoic acid (d)Cyclopentyloxycyclohexane
(e)4-Allyl-2-methoxyphenol (eugenol; from oil of cloves)
How would you carry out the following transformations? More thanone step may be required.
(a)

(b)

(c)

(d)

(e)

Treatment of the following alkene with a peroxy acid yields an epoxide different from that obtained by reaction with aqueous Br2 followed by base treatment. Propose structures for the two epoxides, and explain the result.

Predict the major product of each of the following reactions:

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