Cumulative Substitution/Elimination Practice Problems
cis-4-iodocyclohexanethiol and trans-4-iodocyclohexanethiol produce different substitution products in a reaction with HO−. Draw the mechanisms that explain the formation of different substitution products.
Determine which compound from each of the following pairs will form a cyclic ether more rapidly when deprotonated.
Draw a suitable mechanism for the following reaction.
(Note: replacing the nitrogen atom with –CH– slows down the reaction)
Explain how the rate of the reaction of 1-bromopropane with sodium ethoxide in DMF changes when:
a. The concentrations of both 1-bromopropane and sodium ethoxide are doubled.
b. Ethanol is used as the solvent instead of DMF.
Explain how the rate of the reaction of 2-bromo-2-methylpentane with methanol changes.
a. When we change the alkyl halide to 2-chloro-2-methylpentane.
b. When we change the alkyl halide to 2-chloro-3-methylpentane.
The reaction shown below involves a step where the hydroxy group in the reactant is converted to a good leaving group via protonation. Propose a reasonable mechanism for the reaction.
Two different elimination products can be obtained when the following compound is reacted with sodium methoxide in methanol solvent. Explain why the deuterated product predominates by about a 7:1 ratio.