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문제 31
Magnesium monoperoxyphthalate (MMPP) epoxidizes alkenes much like mCPBA. MMPP is more stable, however, and it may be safer to use for large-scale and industrial reactions. Propose a mechanism for the reaction of trans-2-methylhept-3-ene with MMPP, and predict the structure of the product(s).
문제 32a
Predict the major products of the following reactions.
a. cis-hex-2-ene + mCPBA in chloroform
문제 32b,c
Predict the major products of the following reactions.
b. trans-hex-3-ene + peroxyacetic acid (CH3CO3H) in water
c. 1-methylcyclohexene + MMPP in ethanol
문제 32d,e
Predict the major products of the following reactions.
d. trans-cyclodecene + peroxyacetic acid in acidic water
e. cis-cyclodecene + mCPBA in CH2Cl2, then dilute aqueous acid
문제 33
When 1,2-epoxycyclohexane (cyclohexene oxide) is treated with anhydrous HCl in methanol, the principal product is trans-2-methoxycyclohexanol. Propose a mechanism to account for the formation of this product.
문제 34a,b
Predict the major products of the following reactions, including stereochemistry.
a. cyclohexene + KMnO4/H2O (cold, dilute)
b. cyclohexene + peroxyacetic acid in water
문제 34c,d
Predict the major products of the following reactions, including stereochemistry.
c. cis-pent-2-ene + OsO4/H2O2
d. cis-pent-2-ene + peroxyacetic acid in water
문제 34e
Predict the major products of the following reactions, including stereochemistry.
e. trans-pent-2-ene + OsO4/H2O2
문제 34f
Predict the major products of the following reactions, including stereochemistry.
f. trans-pent-2-ene + peroxyacetic acid in water
문제 35a
Show how you would accomplish the following conversions.
a. cis-hex-3-ene to meso-hexane-3,4-diol
문제 35b
Show how you would accomplish the following conversions.
b. cis-hex-3-ene to (d,l)-hexane-3,4-diol
문제 35c
Show how you would accomplish the following conversions.
c. trans-hex-3-ene to meso-hexane-3,4-diol
문제 35d
Show how you would accomplish the following conversions.
d. trans-hex-3-ene to (d,l)-hexane-3,4-diol
문제 36a
Give structures of the alkenes that would give the following products upon ozonolysis–reduction.
(a)
문제 36b
Give structures of the alkenes that would give the following products upon ozonolysis–reduction.
(b)
문제 36c
Give structures of the alkenes that would give the following products upon ozonolysis–reduction.
(c)
문제 37a
Predict the major products of the following reactions.
(a) (E)-3-methyloct-3-ene + ozone, then (CH3)2S
문제 37b
Predict the major products of the following reactions.
(b) (Z)-3-methyloct-3-ene + warm, concentrated KMnO4
문제 37c,d
Predict the major products of the following reactions.
(c)
(d) 1-ethylcycloheptene + ozone, then (CH3)2S
문제 37e
Predict the major products of the following reactions.
(e) 1-ethylcycloheptene + warm, concentrated KMnO4
문제 37f
Predict the major products of the following reactions.
f. 1-ethylcycloheptene + cold, dilute KMnO4
문제 38
a. Propose a mechanism for the following reaction.
2 (CH3)2C=CH–CH3 + cat. H+ → 2,3,4,4-tetramethylhex-2-ene
b. Show the first three steps (as far as the tetramer) in the BF3–catalyzed polymerization of propylene to form polypropylene.
문제 43
Propose a mechanism for the triolefin process using a metal alkylidene as the catalyst.
문제 44
Show what reagents would be needed to synthesize the pheromone of the omnivorous leafroller (OLR) using olefin metathesis to assemble the molecule at the double bond.
문제 45a
Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.
(a)
문제 45b
Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.
(b)
문제 45c
Show how you would synthesize each compound, starting with alkenes or cycloalkenes that contain no more than six carbon atoms. You may use any additional reagents you need.
(c)
문제 46a
Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.
(a)
문제 46b
Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.
(b)
문제 46c
Predict the major products of the following reactions, and give the structures of any intermediates. Include stereochemistry where appropriate.
(c)
