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Propose a Williamson synthesis of 3-butoxy-1,1-dimethylcyclohexane from 3,3-dimethyl-cyclohexanol and butan-1-ol.

Short Answer

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When Butan-1-ol reacts with tosyl chloride in the presence of pyridine. it gets converted into butyl tosylate in the first step. Pyridine acts as a base here and it abstracts the proton of the hydroxyl group forming oxygen anion which attacks on the tosyl group of tosyl chloride and as a result, chloride ion leaves as a leaving group.

Reaction of butan-1-ol with tosyl chloride

Step by step solution

01

Reaction of butan-1-ol with tosyl chloride

When Butan-1-ol reacts with tosyl chloride in the presence of pyridine. it gets converted into butyl tosylate in the first step. Pyridine acts as a base here and it abstracts the proton of the hydroxyl group forming oxygen anion which attacks on the tosyl group of tosyl chloride and as a result, chloride ion leaves as a leaving group.

Reaction of butan-1-ol with tosyl chloride

02

Williamson ether synthesis

Williamson ether synthesis works best when the nucleophile attacks at primary or methyl carbon. In the next step, when 3,3-dimethyl-cyclohexanol reacts with sodium, it forms sodium salt of 3,3-dimethyl cyclohexanol which then reacts with butyl tosylate (which was prepared in first step) and forms 3-butoxy-1,1-dimethylcyclohexane (which is our required product).

Williamson ether synthesis

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Most popular questions from this chapter

Question: (a) Predict the values of m/zand the structures of the most abundant fragments you would observe in the mass spectrum of di-n-propyl-ether.

(b) Give logical fragmentations to account for the following ions observed in the mass spectrum of 2-methoxypentane: 102,87,71,59,31.

Question. (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 鈥渆thyl ether鈥 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 鈥渂oom鈥. 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.

Write structural formulas for the following compounds

  1. methyl isopropyl ether (b) di-iso-butyl ether (c) 2-methoxyoctane

(d) diallyl ether (e) allyl ethyl ether (f) cycloheptane oxide

(g) trans-2,3-epoxyheptane (h) (2R,3S)-2-ethoxypentan-3-ol (i) cis-2,3-dimethyloxirane

There are two ways of making 2-ethoxyoctane from octan-2-ol using the Williamson ether synthesis. When pure (-) -octan-2-ol of specific rotation -8.240is treated with sodium metal and then ethyl iodide, the product is 2-ethoxyoctane with a specific rotation of -15.60. When pure (-) -octan-2-ol is treated with tosyl chloride and pyridine and then with sodium ethoxide, the product is also 2-ethoxyoctane. Predict the rotation of the 2-ethoxyoctane made using the tosylation/sodium ethoxide procedure, and propose a detailed mechanism to support your prediction.

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

(a) CH3OCH=CH2

(b) CH3CH2OCH(CH3)2

(c) ClCH2CH2OCH3

(d)

e)

f)

g)

h)

i)

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