Skip to Content
Merck
HomeApplicationsChemistry & SynthesisSynthetic MethodsOrganic Reaction Toolbox

Organic Reaction Toolbox

An organic reaction toolbox offers a set of useful tools for the synthesis of small molecules

An organic reaction toolbox is a way to organize useful chemical reactions needed for solving synthetic problems and developing new small molecules. When creating a synthetic pathway, a chemist utilizes numerous reactions to transfer one small molecule into a new one. By using protecting groups and creating molecular complexity more directly, detours to pathways can be avoided. Typically, these reactions are characterized into three broad buckets which determine how the reactants combine to form other products.  

The first bucket focuses on the predictable reaction characteristics of the 19 main functional groups (alkane, alkene, alkyne, alkyl halide, alcohol, ether, thiol, sulfide, ketone, aldehyde, carboxylic acid, ester, acyl halide, acid anhydride, amide, amine, nitrile, epoxide, and aryl). These characteristics determine the reactivity properties when present on a molecule. By focusing on the reactions that can be used for a specific functional group, a scientist limits the reaction options to those plausible for the desired transformation.  

Grouping reactions by the functional groups it generates is another way to classify an organic reaction. Since a chemist typically works backwards from the end molecule, it is helpful to group reactions in this way. For example, if an alcohol is the desired end functional group, one could look at using a Grignard reaction with an aldehyde or a ketone, a reduction reaction of either a carboxylic acid, an aldehyde, a ketone, or an ester, or a hydration reaction of an alkene.

The third type of reaction group focuses on reactions that alter the carbon-carbon skeleton through bond creation or breaking. Tremendous advances in synthetic methods for C-C bond formation now make it possible to choose from over 100 different reactions. These advances are due to various factors, including the development of robust and reliable protocols for cross-coupling, increased accessibility to various organometallic reagents, and the creation and improvement of stoichiometric reagents which serve to place a specific carbon-containing moiety.

Related Technical Articles

  • Acid and Base Chart — Table of Acids & Bases
    Acid and base chart lists the strength of acids and bases (strongest to weakest) in order. Simple to use laboratory reference chart for scientists, researchers and lab technicians.
  • Aldol Condensation Reaction
    The aldol condensation reaction is an organic reaction introduced by Charles Wurtz, who first prepared the β-hydroxy aldehyde from acetaldehdye in 1872.
  • Baeyer-Villiger Oxidation Reaction
    The Baeyer-Villiger oxidation is the oxidative cleavage of a carbon-carbon bond adjacent to a carbonyl, which converts the ketones to esters and the cyclic ketones to lactones.
  • 1-hydrosilatrane
    As a versatile hydride reagent, 1-hydrosilatrane can be used in reduction reactions to synthesize alcohols, amines, their chiral counterparts, and esters from aldehydes/ketones.
  • Asymmetric Catalysis with Chiral Oxazaborolidinium Ions (COBIs)
    Learn about the applications of chiral oxazaborolidinium ions (COBIs) as Lewis acid catalysts in different asymmetric reactions such as cyclopropanation, epoxidation, and radical reactions along with details of their catalytic action.
  • See All (27)

Related Protocols

Find More Articles and Protocols

Related Applications
Lead Discovery
Lead discovery or lead identification for drug discovery utilizes screening methods, such as high throughput screening (HTS) or DNA Encoded Library (DEL) screening, to identify lead compounds.
Reaction Design & Optimization
Chemical reaction design and optimization in organic synthesis aims to precisely alter reaction parameters to achieve optimum results in finding pathways to target molecules.
Cross-Coupling
Cross-coupling is a common reaction in organic chemistry for the creation of C-C, C-N, and C-O bonds with the aid of a metal catalyst.
Metathesis
Olefin metathesis involves an organic reaction that redistributes fragments of alkenes (olefins) by cleavage and transformation of carbon-carbon double bonds.
Photocatalysis
Photoredox catalysis uses visible light and photocatalysts for synthetic transformations like cross-coupling and functionalization reactions.
Fluorination
Fluorination is the introduction of fluorine to a compound via electrophilic fluorination, nucleophilic fluorination, difluoromethylation, trifluoromethylation, or perfluoroalkylation.
C–H Functionalization
C–H functionalization is the reliable and predictable conversion of a C–H into a C–C, C–N, C–O, or C–X bond in a selective and controlled fashion.
Related Product Categories
Buchwald Catalysts & Ligands
Buchwald Catalysts and Ligands enable versatile cross-coupling reactions for C-C, C-N, and other bond formations.
Photocatalysts
Photocatalysis utilizes visible light to activate a chemical reaction. Our extensive portfolio of catalysts and photoreactors enable consistent reactions in photoredox catalysis.
C–H Activation Catalysts
Our unparalleled portfolio of C–H activation catalysts, auxiliaries, and oxidants provide reliable and predictable conversions of C–H bonds to C–C, C–N, C–O or C–X bonds.
Cross-Coupling Catalysts
We offer an extensive portfolio of nickel and palladium catalysts to aid in the creation of C–C, C–N, and C–O bonds through common cross-coupling reactions.
Olefin Metathesis
Explore our exceptional portfolio of olefin metathesis catalysts and take advantage of Grubbs’ technical expertise to advance your research and breakthrough synthesis ideas.
Transition Metal Catalysts
Discover our unparalleled portfolio of transition metal catalysts for your different organic and organometallic chemistry-based applications.
Phosphine Ligands
Explore a wide array of phosphine ligands for cross-coupling reactions and diverse applications.
C-C Bond Forming Reagents
With our portfolio of carbon-carbon bond-forming reagents, your breakthroughs in fundamental carbon-carbon bond formation coupling reactions will feel closer than ever.
Related Services
Small Molecule Library Design
Aldrich Market Select offers online ordering of small molecule libraries and chemistry building blocks for compound management.
SYNTHIA™ Retrosynthesis Software
Our custom cell culture product design experts can offer advice and support as you scale your bioprocess from clinical to commercial supply, assisting with liquid products, dry powder products, selection of raw materials, quality testing, flexible product packaging, and product documentation.
Sign In To Continue

To continue reading please sign in or create an account.

Don't Have An Account?