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Ch. 7 - The Reactions of Alkynes • An Introduction to Multistep Synthesis
Bruice - Organic Chemistry 8th Edition
Bruice8th EditionOrganic ChemistryISBN: 9780135213711Non è quello che usi tu?Cambia libro di testo
Capitolo 7, Problema 20d

What are products of the following reactions?
d.

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Step 1: Identify the reaction type. This is a hydroboration-oxidation reaction of an alkyne. The reagents R₂BH/THF followed by HO⁻, H₂O₂, and H₂O indicate that the alkyne will undergo anti-Markovnikov addition to form an aldehyde or ketone.
Step 2: Analyze the structure of the starting alkyne. The molecule contains a terminal alkyne (triple bond at the end of the chain) with a methyl group attached to the second carbon.
Step 3: In the first step, R₂BH adds to the terminal alkyne in an anti-Markovnikov fashion. The boron atom attaches to the less substituted carbon of the triple bond, forming an organoborane intermediate.
Step 4: In the second step, the organoborane intermediate reacts with hydrogen peroxide (H₂O₂) in the presence of hydroxide ions (HO⁻). This oxidation step converts the boron group into a hydroxyl group (-OH), resulting in the formation of an aldehyde.
Step 5: The final product is an aldehyde with the hydroxyl group replacing the terminal alkyne. The structure of the product will be CH₃-CH₂-CHO (propanal).

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