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The transition states for SN1 reactions that showcases tertiary carbons have the lowest transition state energy level in SN1 reactions. A tertiary carbocation will maximize the rate of reaction for an SN1 reaction by producing a stable carbocation. This happens because the rate determining step of a SN1 reaction is the formation of the carbocation.
Carbocations were also found to be involved in the S N 1 reaction, the E1 reaction, and in rearrangement reactions such as the Whitmore 1,2 shift. The chemical establishment was reluctant to accept the notion of a carbocation and for a long time the Journal of the American Chemical Society refused articles that mentioned them.
A 1,2-rearrangement or 1,2-migration or 1,2-shift or Whitmore 1,2-shift [1] is an organic reaction where a substituent moves from one atom to another atom in a chemical compound. In a 1,2 shift the movement involves two adjacent atoms but moves over larger distances are possible. In the example below the substituent R moves from carbon atom C 2 ...
The reaction involves a carbocation intermediate and is commonly seen in reactions of secondary or tertiary alkyl halides under strongly basic conditions or, under strongly acidic conditions, with secondary or tertiary alcohols. With primary and secondary alkyl halides, the alternative S N 2 reaction occurs.
In cyclic systems, the reaction presents more features of interest. In these reactions, the stereochemistry of the diol plays a crucial role in deciding the major product. 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 this case, tertiary carbocation will react faster than a secondary which will react much faster than a primary. It is also due to this carbocation intermediate that the product does not have to have inversion. The nucleophile can attack from the top or the bottom and therefore create a racemic product.
Using Hammond's postulate, the lower energy of the tertiary transition state means that its structure is relatively closer to its reactants R(tertiary)-X than to the carbocation product when compared to the secondary case. Thus, the tertiary transition state will be more geometrically similar to the R(tertiary)-X reactants than the secondary ...
Tertiary is a term used in organic chemistry to classify various types of compounds (e. g. alcohols, alkyl halides, amines) or reactive intermediates (e. g. alkyl radicals, carbocations). Red highlighted central atoms in various groups of chemical compounds.