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64 Cards in this Set
- Front
- Back
- 3rd side (hint)
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show the initiation, propagation, and termination steps for the monochlorination of cyclohexane.
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11.1
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Write the mechanism for the formation of tetrachloromethane, CCl_4. From the reaction of methane with Cl_2 + hv.
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11.2
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Which of the hydrogens in the following structure is the easiest for a chlorine radical to remove? How many secondary hydrogens does the structure have?
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11.3
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11.4
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How many alkyl chlorides can be obtained from monochlorination of the following alkanes? Disregard stereoisomers.
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11.5
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Calculate the percent yield of each product obtained if chlorination is carried out in the presence of light at room temperature.
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11.6.a
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Calculate the percent yield of each product obtained if chlorination is carried out in the presence of light at room temperature.
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11.6.b
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Calculate the percent yield of each product obtained if chlorination is carried out in the presence of light at room temperature.
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11.6.c
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11.7
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Carry out the calculations that predict 2-bromobutane will be obtained in 98% yield.
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11.8.a
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Carry out the calculations that predict 2-bromo-2,5,5,trimethylhexane will be obtained in 82% yield.
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11.8.b
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would chlorination or bromination produce a greater yield of 1-halo-2,3-dimethylbutane?
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Chlorination, because the halogen is substituting for a primary hydrogen
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11.9.a
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would chlorination or bromination produce a greater yield of 2-halo-2,3-dimehtylbutane?
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Bromination, because the halogen is substitution for a tertiary hydrogen
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11.9.b
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would chlorination or bromination produce a greater yield of 1-halo-2,2-dimethylpropane?
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Because the molecule has only one kind of hydrogen, only one monohalogenated product will be obtained by both bromination and chlorination.
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11.9.c
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How could betanone be prepared from butane?
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11.10
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If 2-methylpropane is brominated at 125 C in the presence of light, what percent of the product will be 2-bromo-2-methylpropane? Compare your answer with 36% for chlorination of 2-methylpropane.
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11.11
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Calculate what percentages of monobromination products would be.
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11.12.a
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Calculate what percentages of monobromination products would be.
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11.12.b
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Calculate what percentages of monobromination products would be.
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11.12.c
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Write out the propagation steps for the addition of HBr to 1-methylcyclohexene in the presence of a peroxide.
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11.13
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product of 2-methyl-2-butene with HBr
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11.14.a
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product of 2-methyl-2-butene with HCl
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11.14.b
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product of 2-methyl-2-butene with HBr and peroxide
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11.14.c
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product of 2-methyl-2-butene with HCl and peroxide
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11.14.d
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What hydrocarbon with molecular formula C_4H_10 forms only two monochlorinated products? Both products are achiral
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11.15.a
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What hydrocarbon with molecular formula C_4H_10 forms only three monochlorinated products? one is achiral.
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11.16
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Two products are formed when methylenecyclohexane reacts with NBS. Explain how each is formed.
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11.16
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How many allylic substituted bromoalkenes are formed from the reaction of 2-pentene with NBS? Disregard stereoisomers
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11.17
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synthesis
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11.19.a
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synthesis
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11.19.b
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synthesis
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11.19.c
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synthesis
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11.19.d
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Give the product, disregard stereoisomers
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10.e.20.a
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Give the product, disregard stereoisomers
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10.e.20.b
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Give the product, disregard stereoisomers
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10.e.20.c
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Give the product, disregard stereoisomers
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10.e.20.d
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Give the product, disregard stereoisomers
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10.e.20.e
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Give the product, disregard stereoisomers
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10.e.20.f
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Identify an alkane with molecular formula C_5H_12 that forms only one monochlorinated product when eared with Cl_2
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10.e.21.a
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Identify an alkane with molecular formula C_7H_12 that forms only seven monochlorinated product when eared with Cl_2
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10.e.21.b
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Give the major product when treated with excess Cl_2 in light. disregard stereoisomers. Br_2 @ 125 degrees?
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10.e.22-23.a
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Give the major product when treated with excess Cl_2 in light. disregard stereoisomers. Br_2 @ 125 degrees?
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10.e.22-23.b
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Give the major product when treated with excess Cl_2 in light. disregard stereoisomers. Br_2 @ 125 degrees?
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10.e.22-23.c
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Major product. disregard stereoisomers.
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10.e.24.a
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Major product. disregard stereoisomers.
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10.e.24.b
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Major product. disregard stereoisomers.
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10.e.24.c
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Major product. disregard stereoisomers.
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10.e.24.d
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Major product. disregard stereoisomers.
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10.e.24.e
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Major product. disregard stereoisomers.
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10.e.24.f
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Iodine does not react with ethane, even though I_2 is more easily cleaved homolytically than the other halogens. explain
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Abstraction of a hydrogen atom from ethane by an iodine radical is a highly endothermic reaction (DEL-H = 101-71=30kcal/mol; see Table 3.2), so the iodine radicals will reform I_2 rather than abstract a hydrogen atom.
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10.e.25
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Propose a mechanism to account for the products formed in the following reaction:
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10.e.26
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The deuterium kinetic isotope effect for chlorination of an alkane is defined in the following equation. Predict whether chlorination or bromination would have a greater deuterium kinetic isotope effect.
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10.e.27
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major product. Disregard stereoisomers.
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10.e.29.a
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major product. Disregard stereoisomers.
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10.e.29.b
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major product. Disregard stereoisomers.
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10.e.29.c
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major product. Disregard stereoisomers.
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10.e.29.d
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major product. Disregard stereoisomers.
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10.e.29.e
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major product. Disregard stereoisomers.
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10.e.29.f
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What stereoisomers would be obtained from the following reaction?
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10.e.31
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synthesis
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10.e.32.a
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synthesis
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10.e.32.b
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synthesis
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10.e.32.c
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synthesis
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10.e.32.d
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synthesis
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10.e.32.e
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