HYDROBORATION Meaning and
Definition
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Hydroboration is a chemical reaction wherein a boron compound, such as borane or boron trihydride, adds to an unsaturated organic compound, typically an alkene or alkyne, under the presence of a catalyst. This reaction is often employed in organic synthesis to introduce boron into organic molecules.
In hydroboration, the boron compound forms a Lewis acid-base adduct with the unsaturated organic compound. The boron atom of the boron compound acts as an electrophile, while the unsaturated carbon atom of the organic compound acts as a nucleophile. The boron atom then adds to the carbon-carbon double or triple bond, forming a boron-carbon bond and converting the unsaturated compound into an alkylborane.
Hydroboration has several notable characteristics that make it a useful tool in synthetic organic chemistry. Firstly, it proceeds with high regioselectivity, meaning that the boron atom predominantly adds to the less substituted carbon atom of the alkene or alkyne. Secondly, it occurs with syn addition, meaning that the hydrogen and boron atoms are added to the same side of the double or triple bond. Thirdly, the reaction proceeds with retention of stereochemistry, particularly when chiral alkylboranes are used.
The products of hydroboration reactions, alkylboranes, can be further transformed into various functional groups through subsequent reactions. Overall, hydroboration is a valuable method for the introduction of boron atoms into organic compounds in a controlled and efficient manner, enabling the synthesis of a wide range of useful organic molecules.
Etymology of HYDROBORATION
The word "hydroboration" is derived from two words: "hydro" and "borate".
1. "Hydro" is a prefix that originates from the Greek word "hudōr", meaning "water". It is commonly used in scientific terms to refer to water or hydrocarbon compounds.
2. "Borate" refers to any compound that contains the element boron, which is commonly found in compounds such as borax. The term "borate" is derived from the chemical name of boron.
Therefore, "hydroboration" refers to a chemical reaction in which boron is combined with a hydrogen compound, usually in the presence of an alkene or alkyne.
