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450 CHAPTER 13 
 
are identical. Therefore, two equivalents of this alkyl 
bromide are expected. 
 
 
 
(b) The oxygen atom is connected to two carbon atoms, 
each of which is sp3 hybridized. As such, treatment with 
HI is expected to cleave each of the CO bonds and 
replace them with CI bonds, giving the following 
diiodide. 
 
 
 
(c) The oxygen atom is connected to two carbon atoms. 
One of these carbon atoms (left) is sp2 hybridized, while 
the other (right) is sp3 hybridized. As such, treatment 
with HBr is expected to cleave only the CO bond 
involving the sp3 hybridized carbon atom. The other 
CO bond is not cleaved. This gives phenol and ethyl 
bromide as products. 
 
 
 
(d) The oxygen atom is connected to two carbon atoms. 
One of these carbon atoms (left) is sp2 hybridized, while 
the other (right) is sp3 hybridized. As such, treatment 
with HI is expected to cleave only the CO bond 
involving the sp3 hybridized carbon atom. The other 
CO bond is not cleaved, giving the following product. 
 
 
 
(e) The oxygen atom is connected to two carbon atoms, 
each of which is sp3 hybridized. As such, treatment with 
HI is expected to cleave each of the CO bonds and 
replace them with CI bonds. One of these carbon 
atoms is a chiral center. Since this position is tertiary, 
cleavage will occur via an SN1 process, so we expect 
racemization. 
 
O
HI
I
I + H2O
(racemic mixture) 
 
(f) The oxygen atom is connected to two carbon atoms, 
each of which is sp3 hybridized. As such, treatment with 
HBr is expected to cleave each of the CO bonds and 
replace them with CBr bonds, giving cyclohexyl 
bromide and ethyl bromide as products. 
 
 
 
 
13.11. 
(a) There are two methods for naming epoxides. In one 
method, the parent will be propane, and the oxygen atom 
is considered to be an epoxy substituent connected to the 
parent at C1 and C2. In addition, there is a methyl 
substituent at C2. 
 
 
According to the second method for naming epoxides, 
the parent is considered to be the oxirane ring, which has 
two methyl groups attached to it, both located at the 2 
position. 
 
 
 
(b) There are two methods for naming epoxides. In one 
method, the parent will be ethane, and the oxygen atom 
is considered to be an epoxy substituent connected to the 
parent at C1 and C2. In addition, there are two phenyl 
substituents at C1. 
 
 
According to the second method for naming epoxides, 
the parent is considered to be the oxirane ring, which has 
two phenyl groups attached to it, both located at the 2 
position. 
 
 
 
(c) There are two methods for naming epoxides, 
although one of these methods will be less helpful 
because the two substituents (connected to the oxirane 
ring) are actually closed in a ring. This makes it difficult 
to name the compound as an oxirane. According to the 
first method for naming ethers, the parent is 
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