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Chapter 4: Q40P (page 234)
Label each hydrogen atom in the following compound as primary (1o), secondary (2o), or tertiary (3o)
(a)
(b)
(c)
(d)
e)
(f)
(a) 
(b)
(c) 
(d) 
(e)
(f) 
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(a) Draw the structure of the transition state for the second propagation step in the chlorination of methane.
Show whether the transition state is product-like or reactant-like and which of the two partial bonds is stronger.
(b) Repeat for the second propagation step in the bromination of methane.
(a) Compute the heats of reaction for abstraction of a primary hydrogen and a secondary hydrogen from propane by a fluorine radical.
(b) How selective do you expect free-radical fluorination to be?
(c) What product distribution you expect to obtain from the free-radical fluorination of propane?
Question: Free-radical chlorination of hexane gives very poor yields of 1 clorohexyane, while cyclohexane can be converted to chlorocyclohexane in good yield.
(a)How do you account for this difference?
(b) What ratio of reactants (cyclohexane and chlorine)
When healthy, Earth’s stratosphere contains a low concentration of ozone (O3)that absorbs potentially harmful ultraviolet (UV) radiation by the cycle shown at right.
Chlorofluorocarbon refrigerants, such as Freon 12 (CF2Cl2), are stable in the lower atmosphere, but in the stratosphere, they absorb high-energy UV radiation to generate chlorine radicals.
The presence of a small number of chlorine radicals appears to lower ozone concentrations dramatically. The following reactions are all known to be exothermic (except the one requiring light) and to have high-rate constants. Propose two mechanisms to explain how a small number of chlorine radicals can destroy large numbers of ozone molecules. Which of the two mechanisms is more likely when the concentration of chlorine atoms is very small?
(a) When n-heptaneburns in a gasoline engine, the combustion process takes place too quickly. The explosive detonation makes a noise called knocking. When 2,2,4 trimethylpentane (isooctane) is burned, combustion takes place in a slower, more controlled manner. Combustion is a free-radical chain reaction, and its rate depends on the reactivity of the free-radical intermediates. Explain why isooctane has less tendency to knock than doesn-heptane
(b) Alkoxy radicals (R-O)are generally more stable than alkyl (R) radicals. Write an equation showing an alkyl free radical (from burning gasoline) abstracting a hydrogen atom from tert-butyl alcohol,(CH3)3COH. Explain whytert-butyl alcohol works as an antiknock additive for gasoline.
(c) Use the information in Table 4-2 (page 203) to explain why toluene (PhCH3) has a very high-octane rating of 111. Write an equation to show how toluene reacts with an alkyl free radical to give a relatively stable radical.
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