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Chapter 4: Q32P (page 233)
Propionitrile(
)is deprotonated by very strong bases. Write resonance forms to show the stabilization of the carbanion that results.
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In the presence of a small amount of bromine, the following light -promoted reaction has been observed.
(a) Write a mechanism for this reaction. Your mechanism should explain how both products are formed. (Hint: Notice which H atom has been lost in both products)
(b) Explain why only this one type of hydrogen atom has been replaced, in preference to any of the other hydrogen atoms in the starting material.
(a) Draw the reaction-energy diagram for the following reverse reaction:
(b) What is the activation energy for this reverse reaction?
(c) What is the heat of reaction (Δ H0 )for this reverse reaction?
Question: For each reaction, estimate whether for the reaction is positive, negative or impossible to predict.
a.
b.The formation of diacetone alcohol:
c.
Use the bond-dissociation enthalpies in Table 4-2 (page 203) to calculate the heats of reaction for the two possible first propagation steps in the chlorination of isobutane. Use this information to draw a reaction-energy diagram like Figure 4-8, comparing the activation energies of the two radicals.
(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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