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The regiochemistry of the halogenation of alkanes is largely determined by the relative weakness of the C–H bonds. This trend is reflected by the faster reaction at tertiary and secondary positions. Free radical chlorination is used for the industrial production of some solvents: [2] CH 4 + Cl 2 → CH 3 Cl + HCl
More generally, Zaytsev's rule predicts that in an elimination reaction the most substituted product will be the most stable, and therefore the most favored. The rule makes no generalizations about the stereochemistry of the newly formed alkene, but only the regiochemistry of the elimination reaction. While effective at predicting the favored ...
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.
After addition to a straight-chain alkene such as ethene (C 2 H 4), the resulting alkane will rapidly and freely rotate around its single sigma bond under normal conditions (i.e. room temperature). Thus whether substituents are added to the same side (syn) or opposite sides (anti) of a double can usually be ignored due to free rotation.
Regiochemistry follows from the reaction mechanism, which exhibits halogen attack on the least-hindered unsaturated carbon. The mechanism for this chain reaction resembles free radical halogenation, in which the peroxide promotes formation of the bromine radical. However, this process is restricted to addition of HBr.
In terms of regiochemistry, hydroboration is typically anti-Markovnikov, i.e. the hydrogen adds to the most substituted carbon of the double bond. That the regiochemistry is reverse of a typical HX addition reflects the polarity of the B δ+-H δ− bonds. Hydroboration proceeds via a four-membered transition state: the hydrogen and the boron ...
Oxymercuration is very regioselective and is a textbook Markovnikov reaction; ruling out extreme cases, the water nucleophile will always preferentially attack the more substituted carbon, depositing the resultant hydroxy group there.
In organic chemistry, an alkane, or paraffin (a historical trivial name that also has other meanings), is an acyclic saturated hydrocarbon. In other words, an alkane consists of hydrogen and carbon atoms arranged in a tree structure in which all the carbon–carbon bonds are single. [1] Alkanes have the general chemical formula C n H 2n+2.