enamine behaves as a nucleophile in much the same way that an enolate anion does, with nucleoph aracter at the carbon alpha to the one bonded to the amine. This is because an enamine has resonar ructures similar to those observed for an enolate: 4 ith this in mind, draw the complete mechanism for the following reaction. 2. H3O+ Br `N
enamine behaves as a nucleophile in much the same way that an enolate anion does, with nucleoph aracter at the carbon alpha to the one bonded to the amine. This is because an enamine has resonar ructures similar to those observed for an enolate: 4 ith this in mind, draw the complete mechanism for the following reaction. 2. H3O+ Br `N
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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draw complete detailed mechanism please.

Transcribed Image Text:**Understanding Enamines as Nucleophiles**
An enamine behaves as a nucleophile in much the same way that an enolate anion does, with nucleophilic character at the carbon alpha to the one bonded to the amine. This is because an enamine has resonance structures similar to those observed for an enolate:
- The diagram shows two resonance structures of an enamine.
- On the left, the enamine is depicted with a nitrogen atom bonded to a carbon that is also part of a double bond with another carbon.
- On the right, the resonance structure shows the nitrogen with a positive charge and a double bond between the carbon and nitrogen, while the carbon bears a negative charge.
**Activity: Reaction Mechanism**
With this in mind, draw the complete mechanism for the following reaction:
1. React an enamine connected to a cyclohexane ring with a compound containing a bromide and pentane chain.
2. Then add water with an acidic proton (\( \text{H}_3\text{O}^+ \)).
**Reaction Outcome:**
- The products are a ketone (cyclohexanone with a pentyl substituent) and dimethylamine.
**Task:**
Draw the step-by-step mechanism to show how the enamine reacts to form the products.
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