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Ch.4 - The Study of Chemical Reactions
Wade - Organic Chemistry 9th Edition
Wade9th EditionOrganic ChemistryISBN: 9780135213728Not the one you use?Change textbook
All textbooksWade 9th EditionCh.4 - The Study of Chemical ReactionsProblem 4
Chapter 4, Problem 4

The reaction of tert-butyl chloride with methanol(CH3)3C—Cl Tert-butylchloride + CH3—OH methanol —> (CH3)C—OCH3 methyltert-butylether + HCl is found to follow the rate equation rate= Kr[(CH3)3C—Cl] c. What is the kinetic order overall?

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1
Identify the rate equation given in the problem: rate = Kr[(CH3)3C—Cl].
Determine the order of reaction with respect to each reactant.
Notice that the rate equation only includes the concentration of tert-butyl chloride, [(CH3)3C—Cl].
Conclude that the reaction is first order with respect to tert-butyl chloride.
Since methanol does not appear in the rate equation, it is zero order with respect to methanol, making the overall kinetic order of the reaction first order.

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Key Concepts

Here are the essential concepts you must grasp in order to answer the question correctly.

Kinetics

Kinetics is the study of the rates of chemical reactions and the factors that affect these rates. It involves understanding how the concentration of reactants influences the speed of a reaction, which is often expressed through rate equations. In this case, the rate equation indicates that the reaction rate depends solely on the concentration of tert-butyl chloride.
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Rate Equation

A rate equation describes the relationship between the rate of a chemical reaction and the concentration of its reactants. The general form includes a rate constant and the concentrations raised to a power, which reflects the order of the reaction with respect to each reactant. For the given reaction, the rate equation shows that the reaction is first-order with respect to tert-butyl chloride.
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Kinetic Order

Kinetic order refers to the sum of the powers of the concentration terms in the rate equation, indicating how the rate of reaction changes with varying concentrations of reactants. In this case, since the rate equation is first-order in tert-butyl chloride and has no other reactants affecting the rate, the overall kinetic order of the reaction is one.
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Related Practice
Textbook Question

Use the bond-dissociation enthalpies in Table 4-2 (page 167) 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 for formation of the two radicals.

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Textbook Question
Deuterium (D) is the hydrogen isotope of mass number 2, with a proton and a neutron in its nucleus. The chemistry of deuterium is nearly identical to the chemistry of hydrogen, except that the C―D bond is slightly stronger than the C―H bond by 5.0 kJ/mol (1.2 kcal/mol). Reaction rates tend to be slower when a C―D bond (as opposed to a C―H bond) is broken in a rate-limiting step.This effect, called a kinetic isotope effect, is clearly seen in the chlorination of methane. Methane undergoes free-radical chlorination 12 times as fast as tetradeuteriomethane (CD4)Faster: CH4 + Cl⋅ —> CH3Cl + HCl relative rate= 12Slower: CD4 + Cl⋅ —> CD3Cl + DClrelative rate= 1 c. Consider the thermodynamics of the chlorination of methane and the chlorination of ethane, and use the Hammond postulate to explain why one of these reactions has a much larger isotope effect than the other.
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Textbook Question
Use bond-dissociation enthalpies [TABLE 4-2], p. 167) to calculate values of ΔH° for the following reactions.a. CH3—CH3 + I2 —> CH3CH2I + HI
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Textbook Question

Free-radical chlorination of hexane gives very poor yields of 1-chlorohexane, 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) would you use for the synthesis of chlorocyclohexane?

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Textbook Question

The following reaction has a value of ΔG° = –2.1 kJ/mol (–0.50 kcal/mol).

CH3Br + H2S ⇌ CH3SH + HBr

a. Calculate Keq at room temperature (25 °C) for this reaction as written.

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Textbook Question
The bromination of methane proceeds through the following steps:1. Br2 + 2 Br• ΔH° (per mole)/+190 kJ (45 kcal)Ea (per mole)/ 190 kJ (45 kcal)2. CH4 + Br• —> CH3+ HBr +73 kJ (17 kcal) 79 kJ (19 kcal) 3. • CH3 + Br2 —> CH3Br + Br -112 kJ (-27 kcal) 4 kJ (1 kcal) a. Draw a complete reaction-energy diagram for this reaction. b. Label the rate-limiting step.
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