Organic Chemistry
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Draw the product(s) formed from the reaction below.
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.
What are the products of the reaction below?
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 products of the reaction below.
Write suitable reagents for the given reaction.
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.
What is the mechanism of the given synthesis?
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.
Propose the mechanism of the acid-catalyzed ring opening of epoxide given below.
Propose the mechanism for the acid-catalyzed ring opening of epoxide given below.
Determine the final products expected in each of the reactions given below.
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)
Give the major products expected in each of the reactions given below. Also, show the stereochemistry.
What is the structure of the product that results from the epoxide addition reaction given below?
The product in the ring opening of the epoxide depends on whether it happened under acidic or basic conditions. For the reaction below, the epoxide opens in the same way under either condition; explain why.
What is the product of the reaction below when epoxide reacts with acid and alcohol?
Organometallic compounds, which are strong nucleophiles, can undergo reactions with epoxides. Draw the product of the following reaction, assuming that the C-Cu bond is ionic.
Consider the following acid-catalyzed ring-opening reaction of an epoxide:
Calculate ΔH° based on the bonds formed and broken.
The following synthesis is carried out via a cationic cyclization cascade.
What is its possible reaction mechanism? (Note: The carbons are numbered for you.)
Propose a mechanism for the following reaction. [Hint: The formation of the carbocation will trigger a cyclization.]
Suggest a plausible mechanism for the following reaction. [Hint: A cyclization will occur after the carbocation is formed.]
Identify structures (I)–(V).
True or False. The major products of the rearrangements of the arene oxides shown below are identical.
Two arene oxides could be generated from 3a1,5a1-dihydropyrene. What are their structures?
What are the structures of the phenols generated from the given arene oxide?
What is the reaction mechanism for the following?
Ethylene oxide reacts readily with OH−. Why does cyclopropane, a compound with the same three-membered ring strain, not react with OH−?
Draw the products for the reaction of the epoxide, cyclopentene oxide, with ethoxide ion.
Determine which of the given reactions below would be faster.
Deuterium replaces hydrogen to show the existence of the NIH shift by determining the major product obtained through the rearrangement of the given arene oxide.
For the given reaction, draw the major product of the carbocation that would form a phenol by losing either H+ or D+ rather than undergoing NIH shift.
Determine the products for the reaction of the epoxide, cyclopentene oxide, with ethylamine.
For the given reaction:
(i) The reaction could also form another product, a seven-membered molecule. Draw the structure of the product.
(ii) Explain why so few of the seven-membered ring molecules (the other product) were formed.