Draw the elimination products for each of the following E2 reactions; if the products can exist as stereoisomers, indicate which stereoisomers are obtained.
d. (2R,3R)-2-chloro-3-methylpentane + high concentration of CH₃O^-

When using sulfuric acid, but in the absence of other nucleophiles like water or bromide ion, less stable alkenes can be isomerized to their more stable isomer. Provide a mechanism for these acid-catalyzed isomerization reactions. [This is one illustration of the principle of microscopic reversibility.]

(b)

For each of the following reactions, draw the major elimination product; if the product can exist as stereoisomers, indicate which stereoisomer is obtained in greater yield.

e. 3-bromo-3-methylpentane + high concentration of CH₃CH₂O⁻

f. 3-bromo-3-methylpentane + CH₃CH2OH

Which alkyl halide in each pair is more reactive in an E2 reaction with hydroxide ion?

c.

d.

What products will be obtained from the E2 reaction of the following alkyl halides?

c.

What is the major elimination product obtained from an E2 reaction of each of the following alkyl halides with hydroxide ion?

f.

What is the major product of the reaction?

What is the major product of the reaction?

What is the major product of the reaction?