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Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Not the one you use?Change textbook
Chapter 8, Problem 20a

What are products of the following reactions?
a. Chemical reaction diagram showing an alkyne reacting with hydrogen and palladium on carbon catalyst.

Verified step by step guidance
1
Step 1: Identify the functional group in the reactant. The reactant contains a triple bond (alkyne) in the carbon chain.
Step 2: Recognize the reaction conditions. The presence of H₂ and Pd/C indicates a catalytic hydrogenation reaction, which converts alkynes to alkanes by adding hydrogen atoms across the triple bond.
Step 3: Understand the mechanism. In catalytic hydrogenation, the triple bond is fully reduced to a single bond (alkane) as two molecules of hydrogen (H₂) are added.
Step 4: Predict the product structure. Replace the triple bond in the reactant with a single bond, and add two hydrogen atoms to the carbons that were part of the triple bond.
Step 5: Verify the stereochemistry. Since Pd/C catalyzes syn addition, the hydrogens are added to the same side of the molecule, but in this case, the product is an alkane, so stereochemistry is not relevant.

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Key Concepts

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

Hydrogenation of Alkynes

Hydrogenation is a chemical reaction that involves the addition of hydrogen (H2) to an unsaturated compound, such as an alkyne. In this process, the triple bond of the alkyne is converted into a double bond (alkene) or a single bond (alkane) depending on the amount of hydrogen added. The reaction typically requires a catalyst, such as palladium on carbon (Pd/C), to facilitate the addition of hydrogen.
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Role of Catalysts

Catalysts are substances that increase the rate of a chemical reaction without being consumed in the process. In hydrogenation reactions, catalysts like Pd/C provide a surface for the reactants to adsorb, allowing for more efficient interaction and reaction. This lowers the activation energy required for the reaction, enabling the hydrogenation to occur under milder conditions.
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Alkyne Structure and Reactivity

Alkynes are hydrocarbons that contain at least one carbon-carbon triple bond, making them more reactive than alkenes and alkanes. The presence of the triple bond allows for various reactions, including hydrogenation, where the reactivity is influenced by the steric and electronic properties of the substituents attached to the carbon atoms. Understanding the structure of alkynes is crucial for predicting the products of their reactions.
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