BackDraw the product or products that will be obtained from the reaction of cis-2-butene and trans-2-butene with each of the following reagents. If a product can exist as stereoisomers, show which stereoisomers are formed.
3. a peroxyacid
What is the major product of the reaction of 2-methyl-2-butene with each of the following reagents?
f. MCPBA (a peroxyacid)
Predict the major products of the following reactions.
a. cis-hex-2-ene + mCPBA in chloroform
Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes.
c. cis-cyclodecene
d. trans-cyclodecene
Predict the products, including stereochemistry where appropriate, for the m-chloroperoxybenzoic acid epoxidations of the following alkenes.
a. cis-hex-2-ene
b. trans-hex-2-ene
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA
(d)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA;
(h)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (vii) 1. mCPBA 2. H2SO4, H2O
(h)
Predict the product(s) that would result when the alkenes are allowed to react under the following conditions: (v) mCPBA;
(k)
Predict the product(s) when each of the following are reacted with mCPBA, making sure to indicate the relative stereochemical outcome. Indicate any racemic mixtures by drawing both enantiomers.
(a)
When producing a chiral molecule, epoxide formation still results in a mixture of enantiomers, despite its stereospecificity.
(b) How is it that a reaction can be stereospecific while still producing two enantiomers?
Rank the reactivity of the following alkenes with mCPBA ( 1 = most reactive , 5 least reactive ).
One way to think about concerted reactions is to imagine them as being stepwise reactions where, besides the slowest step, all others have infinitesimally small activation energies. Considering the hypothetical stepwise mechanism and actual concerted mechanism of epoxide formation, show what a reaction coordinate diagram might look like for each possibility.
(a) Stepwise, hypothetical mechanism: