/*! 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} Problem 102 What should be the product when ... [FREE SOLUTION] | 91影视

91影视

Log out

Learning Materials

Features

Discover

Chapter 8: Problem 102

What should be the product when ethylmethyl ketone is treated with peracetic acid (a) Ethyl acetate (b) Methyl propanoate (c) Both (a) and (b) (d) Only acetic acid

Short Answer

Expert verified
The product is ethyl acetate, option (a).

Step by step solution

01

Understanding the Reaction

Ethylmethyl ketone ( C_4H_8O) is being treated with peracetic acid (CH_3COOOH). This type of reaction involves oxidation, typically leading to the formation of an ester under these conditions due to the Baeyer-Villiger oxidation process.
02

Applying Baeyer-Villiger Oxidation

In a Baeyer-Villiger oxidation reaction, a ketone is converted into an ester when treated with a peracid such as peracetic acid. In this case, ethylmethyl ketone will be transformed. The mechanism involves the migration of the molecule's more substituted carbon group to the adjacent oxygen.
03

Determining the Migrating Group

Between the ethyl group and the methyl group in ethylmethyl ketone, the ethyl group is larger and more electron-donating, thus it migrates more readily according to migratory aptitude. This migration from the carbon adjacent to the carbonyl group in the ketone leads to the formation of the ester.
04

Predicting the Product

By following the migration of the ethyl group, we form an ethyl acetate, which is an ester. The peracetic acid provides the oxygen atom needed to transform the ketone into the ester, resulting in the formation of ethyl acetate.

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!

Key Concepts

These are the key concepts you need to understand to accurately answer the question.

Peracetic Acid
Peracetic acid is a type of peracid, which means it is a particularly powerful oxidizing agent. It is structurally similar to acetic acid but contains an extra oxygen atom, making its formula CH\(_3\)COOOH. This additional oxygen atom is crucial in many chemical reactions, such as the Baeyer-Villiger oxidation.
During this oxidation process, peracetic acid serves as an oxidizing agent. By donating its oxygen atom, it helps transform a ketone into an ester, a reaction that enhances the chemical properties of substances dramatically.

The introduction of peracetic acid in a reaction with ketones, such as ethylmethyl ketone, results in the addition of an oxygen atom adjacent to the carbonyl group of the ketone. This action facilitates the rearrangement necessary for forming an ester, a key aspect of Baeyer-Villiger oxidation.
Keystone to Ester Conversion
In organic chemistry, the interconversion of a ketone to an ester is a significant transformation. This process uses a Baeyer-Villiger oxidation, where peracetic acid plays an essential role. Normally, this transformation involves an oxygen insertion between the carbonyl carbon and one of the adjacent carbon atoms.

For example, when ethylmethyl ketone is exposed to peracetic acid, it undergoes such a transformation. The process extends the functional capabilities of the original ketone by converting it into an ester, specifically ethyl acetate in this scenario. The esterification improves not just the substance's solubility but also alters its reactivity and enhances its potential application in various fields like pharmaceuticals and fragrances.
The mechanism includes the peracid approaching the carbonyl group, inserting an oxygen, and facilitating the migration of an alkyl group to this newly formed ester's oxygen. This is the fundamental principle of turning ketones to esters using peracetic acid in a Baeyer-Villiger reaction.
Migratory Aptitude
Migratory aptitude refers to the tendency of different groups within a molecule to migrate during certain chemical reactions. In the context of the Baeyer-Villiger oxidation, it predicts which group adjacent to the carbonyl carbon will move to the new position. This move happens after the insertion of oxygen by the peracid.

In ethylmethyl ketone, two possible groups can migrate: the ethyl group and the methyl group. The decision hinges on the electron-donating ability and steric effects of these groups.
  • Ethyl group: Larger in size and more electron-donating, it has a higher migratory aptitude.
  • Methyl group: Smaller and less electron-donating.

As a result, the ethyl group is more apt to migrate. This migratory behavior is dictated by the tendency of bulkier and more electron-donating groups to move, due to better stabilization of charges and steric factors. Thus, the transformation of ethylmethyl ketone in the presence of peracetic acid leads to the production of ethyl acetate.

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

Amides undergo hydrolysis to yield carboxylic acid plus amine on heating in either aqueous acid or aqueous base. The conditions required for amide hydrolysis are more severe than those required for the hydrolysis of esters, anhydrides or acid chlorides, but the mechanism is similar (nucleophilic acyl substitution). Nucleophilic acyl substitutions involve a tetrahedral intermediate, hence these are quite different from alkyl substitution \(\left(\mathrm{RCH}_{2} \mathrm{Br} \underset{\mathrm{NaCN}}{\rightarrow} \mathrm{RCH}_{2} \mathrm{CN}\right)\) which involves a pentavalent intermediate or transition state. One of the important reactions of esters is their reaction with two equivalent of a Grignard reagent to give tertiary alcohols. For which functional derivative of carboxylic acids, acidic hydrolysis is avoided? (a) Acid chlorides (b) Acid amides (c) Acid anhydrides (d) Esters

Alkyl halides and alcohols easily undergo nucleophilic substitution either through \(\mathrm{S}_{\mathrm{N}} 1\) or \(\mathrm{S}_{\mathrm{N}} 2\) mechanism. The relative case of these two processes depends upon the nature of the substrate (alkyl group as well as leaving group), nature of nucleophile and also upon the nature of solvent. \(\mathrm{S}_{\mathrm{N}} 1\) mechanism involves the formation of carbocation as intermediate while \(\mathrm{S}_{\mathrm{N}} 2\) mechanism involves the formation of a transition pentavalent state. \(\mathrm{S}_{\mathrm{N}} 1\) is the main mechanism in \(3^{\circ}\) alkyl halides and alcohols, while \(\mathrm{S}_{\mathrm{N}} 2\) mechanism is the path adopted by most of the \(1^{\circ}\) alkyl halides and \(2^{\circ}\) alkyl halides may follow \(\mathrm{S}_{\mathrm{N}} 1\) as well as \(\mathrm{S}_{\mathrm{N}} 2\). Rearrangement of alkyl groups occur when hydrogen halides react with alcohols except with most primary alcohols. The best explanation is that (a) The \(1^{\circ}\) carbocations are unstable and hence are not formed. (b) The \(1^{\circ}\) carbocations are unable to undergo rearrangement. (c) Both (a) and (b) are true (d) Both (a) and (b) are false

The correct order of decreasing basic character is (i) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{NH}_{2}\) (ii) \(\mathrm{C}_{6} \mathrm{H}_{5} \mathrm{CH}_{2} \mathrm{NH}_{2}\) (iii) \(\left(\mathrm{C}_{6} \mathrm{H}_{5}\right)_{2} \mathrm{NH}\) (iv) \(\mathrm{C}_{6} \mathrm{H}_{11} \mathrm{NH}_{2}\) (a) \(\mathrm{ii}>\mathrm{i}>\mathrm{iii}>\mathrm{iv}\) (b) \(\mathrm{iv}>\mathrm{ii}>\mathrm{i}>\mathrm{iii}\) (c) \(\mathrm{iv}>\mathrm{iii}>\mathrm{ii}>\mathrm{i}\) (d) \(\mathrm{iv}>\mathrm{ii}>\mathrm{iii}>\mathrm{i}\)

A new carbon-carbon bond is formed in (i) Aldol condensation (ii) Kolbe's reaction (iii) Reimer-Tiemann reaction (iv) Wurtz Fittig reaction (a) i, iii (b) ii, iii (c) i, iii, iv (d) All of these

What is the molecular weight of a compound that undergoes an aldol self- condensation reaction and whose dehydrated product has a molecular weight of \(70 ?\) (a) 35 (b) 44 (c) 49 (d) 58
See all solutions

Recommended explanations on Chemistry Textbooks

The Earths Atmosphere

Read Explanation

Making Measurements

Read Explanation

Kinetics

Read Explanation

Chemistry Branches

Read Explanation

Nuclear Chemistry

Read Explanation

Organic 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.