Skip to main content
Ch. 22 - Catalysis in Organic Reactions and in Enzymatic Reactions
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
All textbooksBruice 8th EditionCh. 22 - Catalysis in Organic Reactions and in Enzymatic ReactionsProblem 6a
Chapter 23, Problem 6a

a. Draw the mechanism for the following reaction if it involves specific-base catalysis.

Verified step by step guidance
1
Identify the reactants and the product in the reaction. Specific-base catalysis means that the reaction is catalyzed by a base (e.g., OH⁻, a deprotonated species) and not by the solvent itself. This will guide the mechanism.
Determine the functional groups in the reactant that are likely to interact with the base. For example, if the reactant contains an acidic proton (e.g., on an alcohol, carboxylic acid, or alpha-carbon of a carbonyl group), the base will abstract this proton.
Draw the first step of the mechanism: the base abstracts the acidic proton, forming a conjugate base of the reactant. Represent this step using curved arrows to show the movement of electrons. For example, the lone pair on the base attacks the acidic hydrogen, and the bond between the hydrogen and the reactant breaks, leaving the electrons on the reactant.
Illustrate the intermediate formed after the proton abstraction. This intermediate is often a negatively charged species (e.g., an enolate ion if the reactant is a carbonyl compound). Ensure that the structure of the intermediate is drawn correctly, showing all lone pairs and charges.
Complete the mechanism by showing how the intermediate reacts to form the final product. This could involve nucleophilic attack, elimination, or rearrangement, depending on the reaction. Use curved arrows to depict the electron flow in this step, and ensure that the product is consistent with the reaction conditions and specific-base catalysis.

Verified video answer for a similar problem:

This video solution was recommended by our tutors as helpful for the problem above.
Video duration:
2m
Was this helpful?

Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Specific-Base Catalysis

Specific-base catalysis refers to a reaction mechanism where a base, often a specific ion or molecule, facilitates the reaction by abstracting a proton (H+) from a substrate. This process lowers the activation energy required for the reaction to proceed, thereby increasing the reaction rate. Understanding this concept is crucial for analyzing how the base interacts with the reactants and influences the overall mechanism.
Recommended video:
2:50
Acid-Base Catalysis Concept 3

Reaction Mechanism

A reaction mechanism is a step-by-step description of the pathway taken by reactants to form products in a chemical reaction. It includes the sequence of elementary steps, intermediates, and transition states involved. Drawing the mechanism helps visualize how bonds are broken and formed, providing insight into the kinetics and thermodynamics of the reaction.
Recommended video:
Guided course
02:16
Heck Reaction Mechanism

Proton Transfer

Proton transfer is a fundamental process in organic chemistry where a proton (H+) is transferred from one molecule to another. This process is often a key step in acid-base reactions and can significantly influence the stability of intermediates and the overall reaction pathway. Understanding proton transfer is essential for predicting the behavior of reactants under specific catalytic conditions.
Recommended video:
Guided course
03:
Proton Splitting
Related Practice
Textbook Question

Although metal ions increase the rate of decarboxylation of dimethyloxaloacetate, they have no effect on the rate of decarboxylation of either the monoethyl ester of dimethyloxaloacetate or acetoacetate. Explain why this is so.

2
views
Textbook Question

Draw the mechanism if it involves general-acid catalysis.

2
views
Textbook Question

The relative rate of reaction for the cis alkene (E) is given in Table 22.2. What do you expect the relative rate of reaction for the trans alkene to be?

2
views
Textbook Question

Draw the mechanism for the following reaction if it involves specific-acid catalysis.

3
views
Textbook Question

Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating a. similarities. b. differences.

1. acid-catalyzed formation of a hydrate

1
views
Textbook Question

Show all the products, including their configurations, that are obtained from the above reaction.

2
views