12. Alcohols, Ethers, Epoxides and Thiols

Using IUPAC rules, name the following molecules.

(b)

What is each compound's systematic name?

d. CH₃CH₂CH₂OCH₂CH₃

Draw a condensed structure and a skeletal structure for each of the following:

i. 3-ethoxy-2-methylhexane

Draw a condensed structure and a skeletal structure for each of the following:

a. sec-butyl tert-butyl ether

Name the following compounds:

a. CH₃OCH₂CH₃

b. CH₃OCH₂CH₂CH₃

Would you expect the reactivity of a five-membered ring ether such as tetrahydrofuran (Table 10.2) to be more similar to the reactivity of an epoxide or to the reactivity of a noncyclic ether? Why?

In the presence of 18-crown-6, potassium permanganate dissolves in benzene to give "purple benzene," a useful reagent for oxidizing alkenes in an aprotic environment. Use a drawing of the complex to show why KMnO₄ dissolves in benzene and why the reactivity of the permanganate ion is enhanced.

(A true story.) An inexperienced graduate student moved into a laboratory and began work. He needed some diethyl ether for a reaction, so he opened an old, rusty 1-gallon can marked 'ethyl ether' and found there was half a gallon left. To purify the ether, the student set up a distillation apparatus, started a careful distillation, and went to the stockroom for the other reagents he needed. While he was at the stockroom, the student heard a muffled "boom." He quickly returned to his lab to find a worker from another laboratory putting out a fire. Most of the distillation apparatus was embedded in the ceiling.

(a) Explain what probably happened.

(b) Explain how this near-disaster might have been prevented.

Give common names for the following compounds.

(a) (CH₃)₂CHOCH(CH₃)CH₂CH₃

(b) (CH₃)₃COCH₂CH(CH₃)₂

(c) PhOCH₂CH₃

(d) ClCH₂OCH₂CH₂CH₃

Give a common name (when possible) and a systematic name for each compound.

(a) CH₃OCH=CH₂

(b) CH₃CH₂OCH(CH₃)₂

(c) ClCH₂CH₂OCH₃

Write structural formulas for the following compounds.

(d) divinyl ether

(e) allyl methyl ether

(f) cyclohexene oxide

Give a common name (when possible) and a systematic name for each compound.

(d)

(e)

(f)

Name the following:

f.

Name the following:

e.

What are their common names?