Organic Chemistry (9th Edition)
9th Edition
ISBN: 9780321971371
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Chapter 4.13A, Problem 4.18P
What would be the product ratio in the chlorination of propane if all the hydrogens were abstracted at equal rates?
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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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- a) Free radical bromination is more selective than free radical chlorination. Draw a reaction coordinate diagram for the specific step in the radical chain mechanism that illustrates the source of this selectivity, and explain your reasoning. b) Explain why the bond dissociate energy (BDE) of tert-butane is 95 kcal/mol while the BDE for propane is 99 kcal/mol.arrow_forward1-pentanol + HBr -> 1-bromopentane Is this substitution reaction reversible? In other words, would one expect to obtain an equilibrium mixture of the alcohol and bromoalkene at the end of the reaction of would one expect this reaction to go to completion? Justify your answer?arrow_forwardThe Friedel-Crafts Alkylation of p-xylene n-propyl bromide can result in an isopropyl as well as n-propyl substitution. A) Write the chemical equation involved in this reaction. B) Which will be the major and minor product? What do you expect will be the ratio of n-propyl to isopropyl substitution for p-xylene?arrow_forward
- Predict the products of dehydrohalogenation and dehydration reactions, and use Zaitsev’s rule to predict the major and minor productsarrow_forwardQUESTION 3 An organic chemistry class is comparing the elimination rates of for the E1 reaction of chlorocyclohexane and the dehydraton reaction of cyclohexanol. To initially confirm the presence of the double bond in the product of each reaction, a bromine test is performed on a subsample of each completed reaction. The reagent, is added to the product mix, and the expected color change if indeed an alkene has been produced in each mix will be from to O CI4, colorless, yellow O KMN04, purple, colorless O KMNO4, purple, colorless O Br2, red, colorlessarrow_forward1-pentanol + NaBr/H2SO4 -> 1-bromopentane Is this substitution reaction reversible? In other words, would one expect to obtain an equilibrium mixture of the alcohol and bromoalkene at the end of the reaction of would one expect this reaction to go to completion? Justify your answer?arrow_forward
- Substitutions on aromatic rings are generally carried out by electrophilic substitution, but for the synthesis of phenolic compounds and alkoxy benzene it is carried out by nucleophilic substitution, explain why this is so .arrow_forwardAn isomer of tetramethylbenzene undergoes nitration to yield a single product. Based on this information, which isomer(s) of tetramethylbenzene could the starting material have been?arrow_forwardAnswer the following questions regarding the nucleophilic substitution reaction shown below: CH3CH2CH2-Br + I- ------> CH3CH2CH2I + Br- (a) Write the rate law for this reaction assuming that it is a one step reaction that is first order in each of the reactants. (b) Holding the concentration of the iodide ion constant, what change would be observed in the rate if the concentration of the n- propyl bromide was tripled? (b) Assume that this is an exothermic reaction, draw the energy profile and identify the location of the transition state. (c) Draw the transition state for this reaction. (d) What change is observed for the entropy of the system during this reaction? (e) Show the likely mechanism of this reaction using the proper curved arrowsarrow_forward
- Imagine that phenol (“hydroxybenzene”) and nitrobenzene are reacted (in separate beakers) with a hot solution containing both concentrated sulfuric acid and concentrated nitric acid. A) Phenol reacts much more quickly than benzene, and benzene reacts much more quickly that nitrobenzene. Explain this observation, using at least one appropriate reaction coordinate diagram as part of your answer (be sure to label your reaction diagram with appropriate structures). You do not need to include any complete mechanisms, but you may wish to use portions of mechanisms as part of your discussion.arrow_forwardHow are cyclopropanes synthesized from alkenes using carbene reactants and how is the mechanism understood to predict the products. Also, what are the various methods for generating carbenes (including the preparation of Simmons-Smith reagents)arrow_forwardElucidate the structure, hybridization, stability order and factors affecting the stability of an organic intermediate which is formed by the homolytic bond breaking.arrow_forward
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