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This is followed by a second condensation to form HMG-CoA (3-hydroxy-3- methyl-glutaryl-CoA). Reduction of HMG-CoA yields (R)- mevalonate . These first 3 enzymatic steps are called the upper mevalonate pathway.
The cationic rearrangement contraction proceeds through the loss of a leaving group and the migration of an endocyclic bond to the carbocation. Pinacol type rearrangements are often used for this type of contraction. [20] Like the expansion reaction this proceeds with an electron donating group aiding in the migration.
An alkyl group which is situated trans- to the leaving –OH group may migrate to the carbocation center, but cis- alkyl groups migrate at a very low rate. In the absence of trans- alkyl groups, ring contraction may occur as the major product instead, i.e. the ring carbon itself may migrate.
Therefore, both of the depicted structures will exist in a D- and an L-form. : [10] Anti-Markovnikov rearrangement. This product distribution can be rationalized by assuming that loss of the hydroxy group in 1 gives the tertiary carbocation A, which rearranges to the seemingly less stable secondary carbocation B. Chlorine can approach this ...
Living cationic polymerization is a living polymerization technique involving cationic propagating species. [1] [2] It enables the synthesis of very well defined polymers (low molar mass distribution) and of polymers with unusual architecture such as star polymers and block copolymers and living cationic polymerization is therefore as such of commercial and academic interest.
The resulting carbocation is then attacked by a molecule of water. Alternately, the diazo group can be displaced directly by a molecule of water in an S N 2 reaction (path B). Both routes lead to formation of an alcohol .
The mechanism of the Reimer-Tiemann reaction. Chloroform (1) is deprotonated by a strong base (normally hydroxide) to form the chloroform carbanion (2) which will quickly alpha-eliminate to give dichlorocarbene (3); this is the principal reactive species.
These reactions often proceed via carbocation intermediates as shown for the dehydration of cyclohexanol. [5] Some alcohols are prone to dehydration. 3-Hydroxylcarbonyls, called aldols, release water upon standing at room temperature: RC(O)CH 2 CH(OH)R' → RC(O)CH=CHR' + H 2 O. The reaction is induced by dehydrating reagents.