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General structure of a halohydrin, where X = I, Br, F, or Cl Structure of the halohydrin 2-chloroethanol. In organic chemistry a halohydrin (also a haloalcohol or β-halo alcohol) is a functional group in which a halogen and a hydroxyl are bonded to adjacent carbon atoms, which otherwise bear only hydrogen or hydrocarbyl groups (e.g. 2-chloroethanol, 3-chloropropane-1,2-diol). [1]
The initial stereochemistry of the reaction sequence is established in the step where the carbanion attacks the carbonyl. Two sp 3 (tetrahedral) carbons are created at this stage, which allows two different diastereomeric possibilities of the halohydrin intermediate.
In organic chemistry, regioselectivity is the preference of chemical bonding or breaking in one direction over all other possible directions. [1] [2] It can often apply to which of many possible positions a reagent will affect, such as which proton a strong base will abstract from an organic molecule, or where on a substituted benzene ring a further substituent will be added.
Halohydrin formation reaction; Hammick reaction; Hammond principle or Hammond postulate; Hantzsch pyrrole synthesis; Hantzsch dihydropyridine synthesis, Hantzsch pyridine synthesis; Hantzsch pyridine synthesis, Gattermann–Skita synthesis, Guareschi–Thorpe condensation, Knoevenagel–Fries modification; Hantzsch–Collidin synthesis; Harries ...
Stereochemistry, a subdiscipline of chemistry, studies the spatial arrangement of atoms that form the structure of molecules and their manipulation. [1] The study of stereochemistry focuses on the relationships between stereoisomers, which are defined as having the same molecular formula and sequence of bonded atoms (constitution) but differing in the geometric positioning of the atoms in space.
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Formation of a secondary alcohol via alkene reduction and hydration is shown: The hydroboration-oxidation and oxymercuration-reduction of alkenes are more reliable in organic synthesis. Alkenes react with N-bromosuccinimide and water in halohydrin formation reaction. Amines can be converted to diazonium salts, which are then hydrolyzed.
For example, HOCl can react with double bonds in the organic reactant or product via a halohydrin formation reaction. To prevent interference from HOCl, a scavenger is usually added to the reaction to consume the HOCl as it is formed. For example, one can take advantage of the propensity of HOCl to undergo this addition reaction by adding a ...