Log out Go to App
Go to App

Learning Materials

Features

Discover

Chapter 19: Problem 57

The following \(\beta\)-diketone can be synthesized from cyclopentanone and an acid chloride using an enamine reaction.

Short Answer

Expert verified
Answer: The enamine reaction process consists of four main steps: (1) Formation of an enamine from cyclopentanone and a secondary amine; (2) Identifying the correct acid chloride based on the desired product's structure; (3) Nucleophilic attack of the enamine to the carbonyl carbon of the acid chloride, forming a tetrahedral intermediate; (4) Tautomerization of the intermediate to yield the final β-diketone product.

Step by step solution

01

Formation of an Enamine

To perform the enamine reaction, the first step is to form an enamine from a cyclic ketone such as cyclopentanone. This is done by reacting cyclopentanone with a secondary amine, e.g., pyrrolidine. The secondary amine acts as a nucleophile, attacking the carbonyl carbon of cyclopentanone to form an enamine intermediate after the elimination of water.
02

Identify the Correct Acid Chloride

To synthesize the given β-diketone, we need to find the correct acid chloride that will result in the desired product when reacted with the enamine. Based on the structure of the desired product, take note of the substituted alkyl group, which is next to the new carbonyl group. The corresponding acid chloride for this synthesis should have the following structure: \(\text{R-CO-Cl}\), where R is the substituted alkyl group.
03

Nucleophilic Attack of the Enamine to the Acid Chloride

Now that we have the enamine and the specific acid chloride required for the synthesis, the next step is the nucleophilic attack of the enamine to the carbonyl carbon of the acid chloride. This results in the formation of a tetrahedral intermediate with the departure of the chloride ion.
04

Tautomerization

The final step in the enamine reaction is the tautomerization of the formed intermediate to give the final β-diketone product. This involves the transfer of a proton from the nitrogen of the secondary amine to the α-carbon of the diketone, followed by a double bond formation, and the final product will contain the β-diketone functional group.

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

When treated with base, the following compound undergoes an intramolecular aldol reaction to give a product containing a ring (yield \(78 \%\) ).

Many types of carbonyl condensation reactions have acquired specialized names, after the 19th century organic chemists who first studied them. Propose mechanisms for the following named condensations. (a) Perkin condensation: Condensation of an aromatic aldehyde with an acid anhydride (b) Darzens condensation: Condensation of an \(\alpha\)-haloester with a ketone or an aromatic aldehyde

Cyclohexene can be converted to 1-cyclopentenecarbaldehyde by the following series of reactions. Propose a structural formula for each intermediate compound.

Write a mechanism for the hydrolysis of the following iminium chloride in aqueous HCl.

2-Ethyl-1-hexanol was needed for the synthesis of the sunscreen octyl \(p\)-methylcinnamate (See Chapter 23, Chemical Connections: "Sunscreens and Sunblocks"). Show how this alcohol could be synthesized (a) by an aldol condensation of butanal and (b) by a malonic ester synthesis starting with diethyl malonate.
See all solutions

Recommended explanations on Chemistry Textbooks

Physical Chemistry

Read Explanation

Inorganic Chemistry

Read Explanation

Organic Chemistry

Read Explanation

Chemical Reactions

Read Explanation

Making Measurements

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