Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 4.7, Problem 4.10P
- a. Using bond-dissociation enthalpies from Table4-2 (page 167), calculate the heat of reaction for each step in the free-radical bromination of methane.
- b. Calculate the overall heat of reaction.
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When a small amount of iodine is added to a mixture of chlorine and methane, it prevents chlorination from occurring. Therefore, iodine is a free-radical inhibitor for this reaction. Calculate ∆H° values for the possible reactions of iodine with species present in the chlorination of methane, and use these values to explain why iodine inhibits the reaction. (The I¬Cl bond-dissociation enthalpy is 211 kJ>mol or 50 kcal>mol.)
A.) What is the heat of reaction, ΔH°?
CO2(g) + H2O(l) à H2CO3(aq)
–20.2 kJ mol–1
–1379 kJ mol–1
–592 kJ mol–1
B.)
What is the average bond energy in CO2?
CO2(g) ΔH°f, = –393.5 kJ mol–1
CO(g) ΔH°f, = –110.5 kJ mol–1
C(g) ΔH°f, = +715 kJ mol–1
CO32–(aq) ΔH°f, = –676.3 kJ mol–1
O(g) ΔH°f, = +249.0 kJ mol–1
207 kJ mol–1
1607 kJ mol–1
804 kJ mol–1
7. Estimate the enthalpy of reaction (in kJ/mol) for the combustion of methane. Be sure to
show a lewis structure for each molecule.
CH, (g) + 20, (g)
·CO, (g) + H,O (g)
Bond Bond Enthalpy
(kJ/mol)
C-O
351
C=0
799
CEO
1070
O-O
142
O=0
498
C-H
414
O-H
460
Chapter 4 Solutions
Organic Chemistry (9th Edition)
Ch. 4.3A - Draw Lewis structures for the following free...Ch. 4.3B - a. Write the propagation steps leading to the...Ch. 4.3C - Prob. 4.3PCh. 4.3C - Prob. 4.4PCh. 4.4 - The following reaction has a value of G =...Ch. 4.4 - Under base-catalyzed conditions two molecules of...Ch. 4.5B - When ethene is mixed with hydrogen in the presence...Ch. 4.5B - For each reaction, estimate whether S for the...Ch. 4.7 - a. Propose a mechanism for the free radical...Ch. 4.7 - a. Using bond-dissociation enthalpies from...
Ch. 4.8 - The reaction of tert-butyl chloride with methanol...Ch. 4.8 - Under certain conditions, the bromination of...Ch. 4.8 - When a small piece of plat num is added to a...Ch. 4.10 - Prob. 4.14PCh. 4.10 - Prob. 4.15PCh. 4.12 - The bromination of methane proceeds through the...Ch. 4.12 - a. Using me BDEs in Table4-2 (page 167 ), compute...Ch. 4.13A - What would be the product ratio in the...Ch. 4.13A - Classify each hydrogen atom in the following...Ch. 4.13B - Use the bond-dissociation enthalpies in Tabte4-2...Ch. 4.13B - Prob. 4.21PCh. 4.13B - Prob. 4.22PCh. 4.14 - a. Compute the heats of reaction for abstraction...Ch. 4.14 - 2,3-Dimethylbutane reacts with bromine in the...Ch. 4.14 - Prob. 4.25PCh. 4.15 - Prob. 4.26PCh. 4.15 - Prob. 4.27PCh. 4.16A - Prob. 4.28PCh. 4.16A - Prob. 4.29PCh. 4.16B - Prob. 4.30PCh. 4.16C - Prob. 4.31PCh. 4.16C - Acetonitrile (CH3C N) is deprotonated by very...Ch. 4.16D - Prob. 4.33PCh. 4 - The following reaction is a common synthesis used...Ch. 4 - Consider the following reaction-energy diagram. a....Ch. 4 - Draw a reaction-energy diagram for a one-step...Ch. 4 - Draw a reaction-energy diagram for a two-step...Ch. 4 - Prob. 4.38SPCh. 4 - Treatment of tert-butyl alcohol with concentrated...Ch. 4 - Label each hydrogen atom in the following...Ch. 4 - Prob. 4.41SPCh. 4 - Prob. 4.42SPCh. 4 - Prob. 4.43SPCh. 4 - Prob. 4.44SPCh. 4 - Prob. 4.45SPCh. 4 - Prob. 4.46SPCh. 4 - For each compound, predict the major product of...Ch. 4 - When exactly 1 mole of methane is mixed with...Ch. 4 - Prob. 4.49SPCh. 4 - Prob. 4.50SPCh. 4 - Prob. 4.51SPCh. 4 - When dichloromethane is treated with strong NaOH,...Ch. 4 - Prob. 4.53SPCh. 4 - When a small amount of iodine is added to a...Ch. 4 - Prob. 4.55SPCh. 4 - When healthy, Earths stratosphere contains a low...Ch. 4 - Prob. 4.57SPCh. 4 - lodination of alkanes using iodine (I2) is usually...
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- Using bond energies from the table, estimate ΔH for the reaction below. The OH group on the product side is attached to a carbon.CH2=CH2(g) + H2O(g) ↔ CH3CH2OH(g) Bond Energies, kJ/mol Single Bonds H C N O S F Cl Br I H 432 C 411 346 N 386 305 167 O 459 358 201 142 S 363 272 --- --- 286 F 565 485 283 190 284 155 Cl 428 327 313 218 255 249 240 Br 362 285 243 201 217 249 216 190 I 295 213 --- 201 --- 278 208 175 149 Multiple Bonds C=C 602 C=N 615 C=O 799 CºC 835 CºN 887 CºO 1072 N=N 418 N=O 607 S=O (in SO2) 532 NºN 942 O2 494 S=O (in SO3) 469arrow_forwardBalanced chemical equation for the combustion of ethanol as a reference. C₂H5OH (1)+30₂ (g) → 2 CO₂ (g) + 3 H₂O(g) C-H=410 kJ/mol Selected Bond Energies O-H=463 kJ/mol How much energy is required to break the bonds in ethanol? Show your work. C-O=358 kl/mol C-C= 348 kJ/mol H-Carrow_forwardUse the following equations to calculate the heat of the reaction for the synthesis of diborane. 2B(s) + 3/2 O2(g) → B2O3(s) ∆ Ho = -1273 kJ B2H6(g) + 3 O2(g) → B2O3(s) + 3H2O(g) ∆ Ho = -2035 kJ H2(g) + 1/2 O2(g) → H2O(l) ∆ Ho = -286 kJ H2O (l) → H2O (g) Δ Ho = 44 kJ Calculate ∆Ho for the following reaction:2B(s) + 3H2(g) → B2H6(g)arrow_forward
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