Organic Chemistry
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An optically active epoxide is produced when (E)-1,2-dicyclopentylethene is epoxidized in an enantioselective manner using the Jacobsen catalyst. However, the product is optically inactive when the same conditions are utilized using (Z)-1,2-dicyclopentylethene as a substrate. Elucidate this observation.
Draw the product(s) formed when the given alkene undergoes a reaction with mCPBA.
Draw the product(s) formed when the given molecule reacts with mCPBA, followed by sulfuric acid.
Draw the product(s) formed when the given compound reacts with m-CPBA.
Draw the product(s) formed when the given alkene molecule undergoes a reaction with (1) mCPBA and then with (2) H2SO4/H2O.
Determine the reaction's atom economy below and describe the fate of the remaining percentage of material not utilized in the major product.
Draw the products of the reaction of the given molecule with mCPBA.
Indicate the stereochemistry, and draw both enantiomers if the product is a racemic mixture.
Even though the epoxidation reaction is stereospecific, the formation of an epoxide will lead to a mixture of enantiomers while producing a chiral compound.
Why does the reaction form a racemic mixture of products?
Despite the fact that the reaction is stereospecific, the formation of an epoxide will lead to a mixture of enantiomers while producing the chiral molecule.
How can a reaction be stereospecific and still yield two enantiomers?
Rank the following alkenes with respect to relative reactivity with m-CPBA, 1 being the most reactive and 5 being the least.
To gain insight into concerted reactions, one can conceptualize them as stepwise reactions where all steps, except the slowest one, possess exceedingly small activation energies. Illustrate the hypothetical stepwise mechanism by presenting a reaction coordinate diagram for the following example.
To gain insight into concerted reactions, one can conceptualize them as stepwise reactions where all steps, except the slowest one, possess exceedingly small activation energies. Illustrate the actual concerted mechanism of the reaction through a reaction coordinate diagram.
Provide two different pathways to carry out the following reaction.
For the reaction of 3-ethyl-2-methylpent-2-ene with m-CPBA (meta-chloroperoxybenzoic acid), predict the major product.
Illustrate the product(s) that will be formed in the reactions of cis-3-hexene and trans-3-hexene with a peroxyacid. State which stereoisomers are produced, if applicable.
Provide the products for the epoxidation reactions of the following alkenes through m-chloroperoxybenzoic acid. Include stereochemistry where appropriate.
a. cis-but-2-eneb. trans-but-2-ene
a. cis-cyclononeneb. trans-cyclononene
Provide the structure of the major product in the epoxidation reaction given below.
cis-but-2-ene + m-CPBA in chloroform
Epoxides can be synthesized from alkenes using the reagents below. Draw a mechanism for the sequence of reactions below.
Draw the product(s) when the following molecule is reacted with mCPBA. For racemic mixtures, draw both enantiomers.
The formation of an epoxide is stereospecific; this is evidence for its concertedness. If step (ii) in the given hypothetical non-concerted reaction where the original reaction is slowed down, what is the product's distribution change?
m-CPBA is a peracid with a carbonyl group. Explain how the carbonyl weakens the σ bond between the two oxygen atoms which makes hydroxyl a better leaving group.
Give the atom economy for the reaction shown below. Hint: Catalysts and solvents should be excluded.
Propose a multistep synthesis showing how can the target molecule be prepared from the starting material.
Determine the alkene molecule needed to be reacted with a peroxyacid to produce the following epoxide.
(i) cyclopentene oxide
(ii) 2-isopropyloxirane
(i) Draw the alkene molecule needed to produce the following compound:
(ii) Draw any other epoxide formed in the reaction.
(iii) Assign the R and S configuration to each chiral center.
Draw the alkenes needed to react with a peroxy acid to produce the following epoxides:
(i) 2,3-diethyl-2,3-methyloxirane
(ii) 3,4-epoxy-3-ethylhexane