8. Elimination Reactions

What are the products of the following reactions?

g.

h.

Which compound has the greatest rate of hydrolysis at pH = 3.5: benzamide, o-carboxybenzamide, o-formylbenzamide, or o-hydroxybenzamide?

Practice your electron-pushing skills by drawing a mechanism for the following E2 reactions.

(b)

Identify the bonds that break and form in the following elimination reactions.

(b)

If a quaternary ammonium ion can undergo an elimination reaction with a strong base, why can’t a protonated tertiary amine undergo the same reaction?

Indicate how each of the same factors affects an E2 reaction.

1. the strength of the base

2. the concentration of the base

3. the solvent

Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.

e. 3-chloro-3-ethyl-2,2-dimethylpentane + high concentration of CH₃CH₂O^-

cis-1-Bromo-4-tert-butylcyclohexane and trans-1-bromo-4-tert-butylcyclohexane both react with sodium ethoxide in ethanol to form 4-tert-butylcyclohexene. Explain why the cis isomer reacts much more rapidly than the trans isomer.

Draw the structure of DDE.