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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 20e

What are products of the following reactions?
e.

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1
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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Key Concepts

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

Reaction Mechanisms

Understanding reaction mechanisms is crucial in organic chemistry as they describe the step-by-step process by which reactants transform into products. This includes identifying intermediates, transition states, and the movement of electrons. Familiarity with mechanisms helps predict the outcome of reactions and the stability of products formed.
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Functional Groups

Functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. Recognizing functional groups allows chemists to predict reactivity and the types of products that can be formed during chemical reactions. Common functional groups include alcohols, ketones, and carboxylic acids.
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Stereochemistry

Stereochemistry involves the study of the spatial arrangement of atoms in molecules and how this affects their chemical behavior. It is essential for understanding isomerism, where compounds with the same molecular formula can have different structures and properties. Stereochemical considerations can significantly influence the products of reactions, especially in chiral environments.
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