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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 20e

What are products of the following reactions?
e.

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Step 1: Recognize the reaction type. This is a hydroboration-oxidation reaction of an alkyne. The reagents used are R2BH/THF followed by HO⁻, H2O2, and H2O.
Step 2: Understand the regioselectivity. Hydroboration-oxidation of terminal alkynes leads to the formation of an aldehyde due to anti-Markovnikov addition of water across the triple bond.
Step 3: Analyze the first step (hydroboration). The R2BH adds to the less substituted carbon of the terminal alkyne, forming an organoborane intermediate.
Step 4: Analyze the second step (oxidation). The organoborane intermediate reacts with H2O2 and HO⁻, replacing the boron group with a hydroxyl group (-OH), resulting in an enol intermediate.
Step 5: Tautomerization. The enol intermediate undergoes tautomerization to form the more stable aldehyde product. The final product is an aldehyde with the carbonyl group on the terminal carbon.

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