Epoxide Reactions Practice Problems
A range of organometallic compounds, known for their strong nucleophilic properties, can undergo reactions with epoxides. Determine the product of the reaction below. (Note: In the first step, assume that the C–Mg bond is ionic, such that carbon has a negative charge.)
Explain the reason why the reaction of an epoxide given below with an acetylide will not form the target molecule, and determine the side reaction that occurs instead.
In the addition reaction to the epoxide, as shown in the reaction below, the stereochemistry of the epoxide is retained even though this kind of addition happened via the SN2 reaction. Explain the reason behind this retention of stereochemistry.
For the given epoxide, its reaction with an organolithium reagent and subsequent treatment with acid would exclusively generate the initial epoxy alcohol compound. (I) What is the reason for this outcome? (II) What conditions can be altered to the reaction to obtain the intended product?
Determine the expected product(s) of the given reaction and specify its relative stereochemistry. If a racemic mixture is formed, draw both of the enantiomers.
Draw the expected product(s) of the reaction shown below and specify its relative stereochemistry. If a racemic mixture is produced, draw both of the enantiomers.
Determine the major product for the base-catalyzed ring-opening reaction of 2,2-diethyloxirane with 0.1 M NaOH.
Determine the major product for the base-catalyzed ring-opening reaction of 2,2-diethyloxirane with CH3O-/CH3OH.
Suggest a plausible mechanism for the base-catalyzed ring-opening of benzene oxide. In your mechanism, use Nu- as a generic nucleophile.
In determining the major product in the rearrangement of the given arene oxide, NIH shift was established. In this reaction, the hydrogen is replaced by deuterium.
The NIH shift occurs in the reaction; determine the major product.
1,2-epoxycycloheptane is converted into trans-2-methoxycycloheptan-1-ol by treatment with anhydrous HCl in methanol. Propose a mechanism for this reaction.
Show how tetramethylethylene oxide will react when treated with each of the following reagents.
(a) NaOCH2CH3 (sodium ethoxide)
(b) NaNH2 (sodium amide)
(c) NaSPh (sodium thiophenoxide)