**Stork Enamine Reactions****Problem Statement:**Write the mechanism to predict the product of the reaction of acetone with diethylamine (using a Lewis acid catalyst), followed by warming with benzoyl chloride (PhCOCl), and then water.**Introduction:**The Stork enamine reaction involves the formation of an enamine from a ketone or an aldehyde and a secondary amine. This reaction is important in organic synthesis for forming carbon-carbon bonds.**Mechanism Steps:**1. **Enamine Formation:** - Acetone reacts with diethylamine in the presence of a Lewis acid catalyst to form an enamine. This step involves the removal of water and formation of a C=C-N bond.2. **Alkylation with Benzoyl Chloride:** - The enamine undergoes alkylation with benzoyl chloride. The nucleophilic enamine attacks the electrophilic carbonyl carbon of benzoyl chloride, leading to the formation of an intermediate.3. **Hydrolysis:** - The final step involves hydrolysis of the intermediate to regenerate the carbonyl group and form the final product. Water is added to revert the enamine to the original carbonyl form, yielding the desired product.This stepwise process highlights the utility of Stork enamine reactions in complex organic syntheses, particularly in forming carbon-carbon bonds.

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Stork enamine reactions - Write the mechanism to predict the product of reaction of acetone wi catalyst), following by warming with benzoyl chloride (PhCOCI) and the

Chemistry

10th Edition

ISBN:9781305957404

Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Publisher:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste

Chapter1: Chemical Foundations

Section: Chapter Questions

Problem 1RQ: Define and explain the differences between the following terms. a. law and theory b. theory and...

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Aromatic Compounds

Aromatic organic compound or aromatic system is an important class of hydrocarbons under the branch of organic chemistry. Aromatic compounds are also called arenas. The definition of aromatic organic compounds can be stated as a class of organic compounds with a planar cyclic ring of atoms bonded through alternated single and double bonds. Due to these alternating bonds, a peculiar feature termed as ‘resonance’, that is, delocalization of pi electrons or the electrons is shared within the atoms of the ring which are present in the aromatic compounds. The word ‘aromatic’ includes a Greek word ‘aroma’ which means smell, indicating that they were named as such due to the sweet odor they produce. Many well-known flavors such as vanilla, cinnamon, and few scents from flowers are extracted from aromatic compounds. Benzene with chemical formula C6H6 is a very common aromatic compound that contains six atoms of carbon held in the cyclic ring of alternate double bonds. It is also to be noted that not all aromatic compounds contain benzene ring. This can be explained by Huckel’s rule.

Question

**Stork Enamine Reactions**

**Problem Statement:**

Write the mechanism to predict the product of the reaction of acetone with diethylamine (using a Lewis acid catalyst), followed by warming with benzoyl chloride (PhCOCl), and then water.

**Introduction:**

The Stork enamine reaction involves the formation of an enamine from a ketone or an aldehyde and a secondary amine. This reaction is important in organic synthesis for forming carbon-carbon bonds.

**Mechanism Steps:**

1. **Enamine Formation:**
- Acetone reacts with diethylamine in the presence of a Lewis acid catalyst to form an enamine. This step involves the removal of water and formation of a C=C-N bond.

2. **Alkylation with Benzoyl Chloride:**
- The enamine undergoes alkylation with benzoyl chloride. The nucleophilic enamine attacks the electrophilic carbonyl carbon of benzoyl chloride, leading to the formation of an intermediate.

3. **Hydrolysis:**
- The final step involves hydrolysis of the intermediate to regenerate the carbonyl group and form the final product. Water is added to revert the enamine to the original carbonyl form, yielding the desired product.

This stepwise process highlights the utility of Stork enamine reactions in complex organic syntheses, particularly in forming carbon-carbon bonds.

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