Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 20: Q61P (page 1038)

There are three dioxane isomers: 1,2-dioxane, 1,3- dioxane, and 1,4-dioxane. One of these acts like an ether and is an excellent solven for Grignard reactions. Another one is potentially explosive when heated. The third one quickly hydrolyzes in dilute acid. Show which isomer acts like a simple ether, and then explain why one of them is potentially explosive. Propose a mechanism for the acid hydrolysis of the third isomer.

Short Answer

Expert verified

behaves like a simple ether. easily hydrolyzes in aqueous acid. is potentially explosive.

Mechanism for acidic hydrolysis of 1, 3 dioxanes

Step by step solution

01

Predicting the behavior of given isomers

1, 4 dioxanes behaves like a simple ether and it is a good solvent for Grignard reaction.

1, 3 dioxanes easily hydrolyzes in aqueous acid.

1, 2 dioxanes is potentially explosive. The bonds between oxygen atoms in a peroxide stores an enormous amount of energy and is very susceptible to being broken

02

Acid hydrolysis of  1, 3 dioxane

1, 3 dioxanes on acidic hydrolysis forms methanal (formaldehyde).

Mechanism for acidic hydrolysis of 1, 3 dioxanes.

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.

Start your free trial

Over 30 million students worldwide already upgrade their learning with Vaia!

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) Give the products expected when acetic formic anhydride reacts with

(i) aniline and

(ii) benzyl alcohol

(b) Propose mechanisms for these reactions.

Question: Rank the compounds in each set in order of increasing acid strength.

(a)CH3CH2COOH,CH3CHBrCOOH,CH3CBr2COOH

(b) CH3CH2CH2CHBrCOOH,CH3CH2CHBrCH2COOH,CH3CHBrCH2CH2COOH

(c)

,CH3CH2COOH,

Question: A carboxylic acid has two oxygen atoms, each with two nonbonding pairs of electrons.

  1. Draw the resonance forms of a carboxylic acid that is protonated on the hydroxy oxygen atom.
  2. Compare the resonance forms with those given previously for an acid protonated on the carbonyl oxygen atom.
  3. Explain why the carbonyl oxygen atom of a carboxylic acid is more basic than the hydroxy oxygen.

Show how you would synthesize the following compounds from the appropriate carboxylic acids or acid derivatives.

(a)

(b)

(c)

Tributylin hydride (Bu3SnH)is used synthetically to reduce alkyl halides, replacing a halogen atom with hydrogen. Free-radical initiators promote this reaction, and free-radical inhibitors are known to slow or stop it. You job is to develop a mechanism, using the following reaction as an example.

The following bond-dissociation enthalpies may be helpful:

(a) Propose initiation and propagation steps to account for this reaction.

(b) Calculate values of ΔH for your proposed steps to show that they are energetically feasible. (Hint: A trace of Br2 and light suggests it’s there only as an initiator, to create Brradicals. Then decide which atom can be extracted most favorably from the starting materials by the Brradical. That should complete the initiation. Finally, decide what energetically favored propagation steps will accomplish the reaction).
See all solutions

Recommended explanations on Chemistry Textbooks

Ionic and Molecular Compounds

Read Explanation

Kinetics

Read Explanation

Physical Chemistry

Read Explanation

Making Measurements

Read Explanation

The Earths Atmosphere

Read Explanation

Nuclear Chemistry

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.

Sign-up for free