Jove
Visualize
Contact Us
JoVE
x logofacebook logolinkedin logoyoutube logo
ABOUT JoVE
OverviewLeadershipBlogJoVE Help Center
AUTHORS
Publishing ProcessEditorial BoardScope & PoliciesPeer ReviewFAQSubmit
LIBRARIANS
TestimonialsSubscriptionsAccessResourcesLibrary Advisory BoardFAQ
RESEARCH
JoVE JournalMethods CollectionsJoVE Encyclopedia of ExperimentsArchive
EDUCATION
JoVE CoreJoVE BusinessJoVE Science EducationJoVE Lab ManualFaculty Resource CenterFaculty Site
Terms & Conditions of Use
Privacy Policy
Policies

Related Concept Videos

Hydroboration-Oxidation of Alkenes03:08

Hydroboration-Oxidation of Alkenes

9.1K
In addition to the oxymercuration–demercuration method, which converts the alkenes to alcohols with Markovnikov orientation, a complementary hydroboration-oxidation method yields the anti-Markovnikov product. The hydroboration reaction, discovered in 1959 by H.C. Brown, involves the addition of a B–H bond of borane to an alkene giving an organoborane intermediate. The oxidation of this intermediate with basic hydrogen peroxide forms an alcohol.
9.1K
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation02:47

Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation

19.0K
Introduction
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.
19.0K
Regioselectivity and Stereochemistry of Hydroboration02:36

Regioselectivity and Stereochemistry of Hydroboration

8.4K
A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...
8.4K
Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis01:13

Esters to Carboxylic Acids: Acid-Catalyzed Hydrolysis

3.2K
Hydrolysis of esters under acidic conditions proceeds through a nucleophilic acyl substitution. In the presence of excess water, the reaction proceeds in a reversible manner, forming carboxylic acids and alcohols.
During hydrolysis, the ester is first activated towards nucleophilic attack through the protonation of the carboxyl oxygen atom by the acid catalyst. The protonation makes the ester carbonyl carbon more electrophilic. In the next step, water acts as a nucleophile and adds to the...
3.2K
Preparation of Alcohols via Addition Reactions02:15

Preparation of Alcohols via Addition Reactions

6.6K
Overview
The acid-catalyzed addition of water to the double bond of alkenes is a large-scale industrial method used to synthesize low-molecular-weight alcohols. An acidic atmosphere is required to allow the hydrogen in the water molecule to act as an electrophile and attack the double bond in an alkene. The addition of a proton to the double bond creates a carbocation intermediate. The proton preferentially bonds to the less substituted end of the double bond to create a more stable carbocation...
6.6K
Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism01:13

Carboxylic Acids to Esters: Acid-Catalyzed (Fischer) Esterification Mechanism

8.2K
Carboxylic acids react with alcohols to yield esters via an acid-catalyzed condensation reaction called Fischer esterification. This is a nucleophilic acyl substitution reaction that proceeds via a tetrahedral intermediate, where a water molecule is eliminated as the leaving group.
8.2K

You might also read

Related Articles

Articles linked to this work by shared authors, journal, and citation graph.

Sort by
Same author

Correction to "Covalent Adaptable Networks from Commodity Polybutadiene and Rubber Waste".

JACS Au·2026
Same author

Covalent Adaptable Networks from Commodity Polybutadiene and Rubber Waste.

JACS Au·2026
Same author

Donor-Acceptor Stenhouse Adducts as Intrinsically Photoswitchable Dynamic Covalent Bonds.

Journal of the American Chemical Society·2025
Same author

Polyacrylamide Hydrogels with Reversibly Photocontrolled Stiffness for 2D Mechanobiology.

ACS applied materials & interfaces·2025
Same author

Electrochemical DABCOylation enables challenging aromatic C-H amination.

Research square·2025
Same author

Internal Catalysis in Dynamic Hydrogels with Associative Thioester Cross-Links.

ACS macro letters·2024

Related Experiment Video

Updated: Sep 23, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.9K

Internal and External Catalysis in Boronic Ester Networks.

Boyeong Kang1, Julia A Kalow1

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, United States.

ACS Macro Letters
|May 16, 2022
PubMed
Summary

Dynamic polymer networks utilize boronic acid-diol chemistry for adaptability. This study reveals how diol structure and additives accelerate bond exchange, enhancing material properties.

More Related Videos

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.7K

Related Experiment Videos

Last Updated: Sep 23, 2025

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions
08:56

Synthesis of a Borylated Ibuprofen Derivative Through Suzuki Cross-Coupling and Alkene Boracarboxylation Reactions

Published on: November 30, 2022

2.9K
Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
07:36

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy

Published on: November 9, 2019

8.1K
Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators
06:31

Highly Stereoselective Synthesis of 1,6-Ketoesters Mediated by Ionic Liquids: A Three-component Reaction Enabling Rapid Access to a New Class of Low Molecular Weight Gelators

Published on: November 27, 2015

9.7K

Area of Science:

  • Polymer Chemistry
  • Materials Science
  • Supramolecular Chemistry

Background:

  • Dynamic materials possess adaptable, self-healing, and responsive properties due to reversible chemical bonds.
  • The mechanical characteristics of dynamic polymer networks are governed by the thermodynamics and kinetics of bond exchange reactions.

Purpose of the Study:

  • To investigate how diol structure and salt additives influence the rate of boronic acid-diol bond exchange.
  • To determine the impact of these factors on binding affinity and the mechanical properties of polymer networks.

Main Methods:

  • Studied the kinetics of boronic acid-diol bond exchange.
  • Analyzed binding affinities between boronic acids and diols.
  • Evaluated mechanical properties of dynamic polymer networks using stress relaxation tests.

Main Results:

  • Proximal amides and buffering anions were found to significantly accelerate the rate of boronic acid-diol bond exchange.
  • This rate acceleration was attributed to internal (amide) and external (anion) catalysis.
  • The enhanced bond exchange kinetics directly correlated with improved stress relaxation in the polymer gels.

Conclusions:

  • The findings provide a fundamental understanding of boronic ester dynamic bonds.
  • Molecular strategies involving diol structure modification and additive use can effectively tune the properties of dynamic materials.