CHM 2211C Chapter 11 Sample Name: _________________
Part M_3: E1 Mechanism of an Alkyl Halide 10 points
The E1 reaction occurs in two steps. The first is rate-limiting , and a carbocation is generated as an intermediate. The second step is a fast step with the loss of a hydrogen ion to form the double bond.
2-bromo-2-methylbutane is treated with ethoxide ion in ethanol and the E1 involves two steps yielding 97% product. The first step is the spontaneous unimolecular dissociation of the alkyl halide which is the rate determining step. (See figure 11.9 page 358) Show this mechanism vertically below: