The solvolysis of 2-bromo-3-methylbutane potentially can give several products, includingboth E1 and SN1 products from both the unrearranged carbocation and the rearranged carbocation. Mechanisms 6-6 (page 253) and 6-9 (previous page) show the products from therearranged carbocation. Summarize all the possible products, showing which carbocation theycome from and whether they are the products of E1 or SN1 reactions.
Solvolysis is a type of nucleophilic substitution (SN1) or elimination where the nucleophile is a solvent molecule.
Nucleophilic substitution is a fundamental class of reactions in which an electron rich nucleophile selectively bonds with or attacks the positive or partially positive (+ve)charge of an atom or a group of atoms to replace a leaving group.
In elimination reaction two substituents are removed from a molecule in either a one or two-step mechanism. The one-step mechanism is known as the E2 reaction, and the two-step mechanism is known as the E1 reaction.
The solvolysis of 2-bromo-3-methylbutane can be carried out by the following five different ways:-
In this reaction 2-bromo-3-methylbutane on ionization form unrearranged 2o carbocation, which on shift of hydride gives the rearranged 3o carbocation.
The unrearranged 2o carbocation on nucleophilic substitution reaction (SN1) form 2-ethoxy-3-methylbutane. 3o carbocation undergoes E1 reaction ,form 3-methylbutene, on further elimination reaction it form 3-methylbut-2-ene.
The rearranged 2o carbocation on nucleophilic substitution reaction (SN1) form 2-ethoxy-3-methylbutane. 2o carbocation undergoes E1 reaction ,form 2-methylbutene, on further elimination reaction it form 3-methylbut-2-ene.