/*! This file is auto-generated */ .wp-block-button__link{color:#fff;background-color:#32373c;border-radius:9999px;box-shadow:none;text-decoration:none;padding:calc(.667em + 2px) calc(1.333em + 2px);font-size:1.125em}.wp-block-file__button{background:#32373c;color:#fff;text-decoration:none} 14-26P Predict the major product when e... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 14: 14-26P (page 737)

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)

Short Answer

Expert verified

(a)

(b)

(c)

(d)

(e)

(f)

Step by step solution

01

Base catalyzed opening of epoxides

Epoxides are considered to be more reactive since opening the epoxide ring relieves the strain of the three-membered ring. Strong bases can attack and open epoxides, even though the leaving group is an alkoxide. Amines can also open epoxides.

02

Predicting major products

(a) Ethylene oxide when reacts with sodium ethoxide gives 2-ethoxy ethanol as the major product.

(b) Ethylene oxide when reacts with sodium amide gives 2-amino ethanol (ethanolamine) as the major product.

(c) Ethylene oxide when reacts with sodium phenoxide gives 2-(phenylthio)ethanol as the major product.

(d) Ethylene oxide when reacts with aniline gives N-phenyl ethanolamine as the major product.

(e) Ethylene oxide when reacts with potassium cyanide gives 2-cyanoethanol as the major product.

(f) Ethylene oxide when reacts with sodium azide gives 2-azidoethanol as the major product.

Unlock Step-by-Step Solutions & Ace Your Exams!

  • Full Textbook Solutions

    Get detailed explanations and key concepts

  • Unlimited Al creation

    Al flashcards, explanations, exams and more...

  • Ads-free access

    To over 500 millions flashcards

  • Money-back guarantee

    We refund you if you fail your exam.

Over 30 million students worldwide already upgrade their learning with 91影视!

One App. One Place for Learning.

All the tools & learning materials you need for study success - in one app.

Get started for free

Most popular questions from this chapter

(a) When ethylene oxide is treated with anhydrous HBr gas, the major product is 1,2-dibromoethane. When ethylene oxide is treated with concentrated aqueous HBr, the major product is ethylene glycol. Use mechanisms to explain these results.

(b) Under base-catalyzed conditions, several molecules of propylene oxide can react to give short polymers. Propose a mechanism for the base-catalyzed formation of the following trimer.

Question. Propose a mechanism for the following reaction.

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?

Propylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.

(a) Draw the enantiomers of propylene oxide.

(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propyleneoxide.

(c) Propose a mechanism for the base-catalyzed hydrolysis of pure (R)-propyleneoxide.

(d) Explain why the acid-catalyzed hydrolysis of optically active propylene oxide gives a product with lower enantiomeric excess and a rotation opposite that of the product of the base- catalyzed hydrolysis.

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.

See all solutions

Recommended explanations on Chemistry Textbooks

Chemical Reactions

Read Explanation

Chemical Analysis

Read Explanation

Ionic and Molecular Compounds

Read Explanation

The Earths Atmosphere

Read Explanation

Nuclear Chemistry

Read Explanation

Kinetics

Read Explanation
View all explanations

What do you think about this solution?

We value your feedback to improve our textbook solutions.

Study anywhere. Anytime. Across all devices.