Answer
The expected solvolysis products are: 1-ethoxy-2,2-dimethylbutane, (E)-3-methylpent-2-ene, 3-methylenepentane and 3-ethoxy-3-methylpentane.
Work Step by Step
First, the given reactant forms an unstable primary carbocation which can lead to two reaction paths:
1) The SN1 reaction with EtOH which leads to the formation of 1-ethoxy-2,2-dimethylbutane;
2) The primary carbocation rearrangement which leads to the formation of a tertiary carbocation.
The tertiary carbocation can then follow the E1 and SN1 reaction mechanisms. The E1 mechanism leads to the formation of two products: (E)-3-methylpent-2-ene (major product) and 3-methylenepentane (minor product). The SN1 mechanism leads to the formation of 3-ethoxy-3-methylpentane via EtOH attack.
