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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.

Short Answer

Expert verified

Answer

(a) Ethers form peroxides on long-term exposure to air, and peroxides are explosive when heated.

(b) Peroxide formation can be prevented by excluding oxygen. Peroxides can also be destroyed by treatment with reducing agents.

Step by step solution

01

Distillation

Distillation is the kind of process in which a liquid is converted into vapors, and these vapors are again condensed to form a liquid.This process starts by heating of liquid to its boiling point.

02

Cause of explosion

(a) Ethers tend to form peroxides on long-term exposure to air which are unstable species due to very reactive O-O bond present in them. When this bond breaks, peroxides decompose into reactive oxygen species, free radicals, and are highly reactive. Peroxides are explosive when concentrated or heated, and for this reason, ethers should never be distilled to dryness.

03

Prevention of explosion

(b) Peroxide formation can be prevented by excluding oxygen. Peroxides can be easily destroyed in a safe manner by treating them with reducing agents such as ferrous sulphate or sodium metabisulphite. Also, potassium iodide can also be added in ethers to remove peroxides.

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Most popular questions from this chapter

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)

Question. The 2001 Nobel Prize in Chemistry was awarded to three organic chemists who have developed methods for catalytic asymmetric synthesis. An asymmetric (or enantioselective) synthesis is one that converts an achiral starting material into mostly one enantiomer of a chiral product. K. Barry Sharpless (The Scripps Research Institute) developed an asymmetric epoxidation of allylic alcohols that gives excellent chemical yields and greater than 90% enantiomeric excess.

The Sharpless epoxidation uses tert-butyl hydroperoxide, titanium(IV) isopropoxide, and a dialkyl tartarate ester as the reagents. The following epoxidation of geraniol is typical.

  1. Which of these reagents is most likely to be the actual oxidizing agent? That is, which reagent is reduced in the reaction? What is the likely function of the other reagents?
  2. When achiral reagents react to give a chiral product, that product is normally formed as a racemic mixture of enantiomers. How can the Sharpless epoxidation give just one nearly pure enantiomer of the product?
  3. Draw the other enantiomer of the product. What reagents would you use if you wanted to epoxidize geraniol to give this other enantiomer?

Predict the major product when each reagent reacts with ethylene oxide.

(a) NaOCH2CH3(Sodium ethoxide)

(b) NaNH2(sodium amide)

(c) NaSPh (sodium thiophenoxide)

(d) PhNH2(aniline)

(e) KCN (potassium cyanide)

(f) NaN3(soidum azide)

Boron tribromide(BBr3)cleaves ethers to give alkyl halides and alcohols.

The reaction is thought to involve attack by a bromide ion on the Lewis acid-base adduct of the ether with(BBr3)(a strong Lewis acid). Propose a mechanism for the reaction of butyl methyl ether with(BBr3)to give (after hydrolysis) butan-1-ol and bromomethane.

Question: Show how you would convert pent-1-eneto each of the following compounds. You may use any additional reagents and solvents you need.

(a) 2-methoxypentane

(b) 1-methoxypentane

(c) 1-methoxypentan-2-ol

(d) 2-methoxypentan-1-ol

(e) 1-phenylpentan-2-ol

(f) 2-methoxy-1-phenylpentane

See all solutions

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