CHM 2211C Chapter 11 Sample Name: ____________________

Chapter 11 Part M_4: E2 Mechanism of Alkyl halides 10 points

The E2 Reaction occurs when an alkyl halide is treated with a strong base, such as hydroxide ion or alkoxide ion (RO^1-). The reaction takes place in a single step through a transition state in which the double bond begins to form at the same time the H and X groups are leaving. :

What product would you expect to obtain from E2 reaction of OH^1- with

(R)-2-bromobutane? Show the stereochemistry of the (1) reactant with the OH ion, (2) the transition state and (3) the product?

Arrange the following in order of less S_n2 reactive to more S_n2 reactive for the following and draw the structure:

Methyl bromide, Ethyl Bromide, isopropyl bromide, Tert-butyl bromide, neopentyl bromide, Vinyl bromide, Phenyl bromide.

Are any of the above Non-reactive via S_n2?