Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 10.SE, Problem 21MP
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Define the Mechanism of the Radical Addition of HBr to an Alkene ?
2-chloropropane is a major product of the reaction of chlorine with propane under ultraviolet light. Write the mechanism for this reaction including the initiation step and the two propagation steps.
Similar to alkanes, hydrogen gas can undergo radical bromination according to the reactionbelow. Propose a chain-reaction mechanism for this reaction, including an initiation step, propagation steps, and two plausible termination steps. The homolytic bond dissociation energy for Br-Br is 46 kcal*mole^-1, for H-Br is 88 kcal*mole^-1 and for H-H is 104 kcal*mole^-1
Chapter 10 Solutions
Organic Chemistry
Ch. 10.1 - Prob. 1PCh. 10.1 - Draw structures corresponding to the following...Ch. 10.2 - Prob. 3PCh. 10.2 - Taking the relative reactivities of 1°, 2°, and...Ch. 10.4 - Prob. 5PCh. 10.4 - The major product of the reaction of...Ch. 10.4 - Prob. 7PCh. 10.5 - Prob. 8PCh. 10.6 - Prob. 9PCh. 10.6 - How might you replace a halogen substituent by a...
Ch. 10.7 - How would you carry out the following...Ch. 10.8 - Rank both sets of compounds in order of increasing...Ch. 10.8 - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 14VCCh. 10.SE - Prob. 15VCCh. 10.SE - Prob. 16VCCh. 10.SE - Draw the electron-pushing mechanism for each...Ch. 10.SE - Draw the electron-pushing mechanism for the...Ch. 10.SE - The formation of Br2 from NBS first involves the...Ch. 10.SE - In light of the fact that tertiary alkyl halides...Ch. 10.SE - Alkyl halides can be reduced to alkanes by a...Ch. 10.SE - Name the following alkyl halides:Ch. 10.SE - Prob. 23APCh. 10.SE - Draw and name all of the monochlorination products...Ch. 10.SE - How would you prepare the following compounds,...Ch. 10.SE - Prob. 26APCh. 10.SE - A chemist requires a large amount of...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product(s) would you expect from the reaction...Ch. 10.SE - What product would you expect from the reaction of...Ch. 10.SE - Rank the compounds in each of the following series...Ch. 10.SE - Which of the following compounds have the same...Ch. 10.SE - Tell whether each of the following reactions is an...Ch. 10.SE - Prob. 34APCh. 10.SE - Alkylbenzenes such as toluene (methylbenzene)...Ch. 10.SE - Prob. 36APCh. 10.SE - Prob. 37APCh. 10.SE - Prob. 38APCh. 10.SE - Prob. 39APCh. 10.SE - Prob. 40APCh. 10.SE - The syntheses shown here are unlikely to occur as...Ch. 10.SE - Why do you suppose its not possible to prepare a...Ch. 10.SE - Prob. 43APCh. 10.SE - Identify the reagents a–c in the following...Ch. 10.SE - Prob. 45APCh. 10.SE - Prob. 46APCh. 10.SE - Prob. 47APCh. 10.SE - The relative rate of radical bromination is...Ch. 10.SE - Prob. 49APCh. 10.SE - Predict the product and provide the entire...
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- Following is a balanced equation for bromination of toluene. (a) Using the values for bond dissociation enthalpies given in Appendix 3, calculate H0 for this reaction. (b) Propose a pair of chain propagation steps and show that they add up to the observed reaction. (c) Calculate H0 for each chain propagation step. (d) Which propagation step is rate-determining?arrow_forwardWrite the propagation steps leading to the formation of dichloromethane (CH2Cl2) from chloromethanearrow_forwardCumene -> i. Butyl chloride ii. Dimethyl amine iii. H2, Pt Provide the bond-line structures for the major organic products obtained in each steparrow_forward
- When exactly 1 mole of methane is mixed with exactly 1 mole of chlorine and light is shone on the mixture, a chlorination reaction occurs. The products are found to contain substantial amounts of di-, tri-, and tetrachloromethane, as well as unreacted methane. Explain how a mixture is formed from this stoichiometric mixture of reactants, and propose mechanisms for the formation of these compounds from chloromethane.arrow_forwardThe rate law for addition of Br2 to an alkene is first order in Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2 to an alkene proceeds in the same manner as for addition of HBr? Explain.arrow_forwardWhich is more stable - a phenyl radical, [C6H5]•, or a benzyl radical, [C6H5CH2]• - and why?arrow_forward
- The rate law for addition of Br2 to an alkene is first orderin Br2 and first order in the alkene. Does this informationsuggest that the mechanism of addition of Br2 to analkene proceeds in the same manner as for addition of HBr?Explain.arrow_forwardThe following alcohols react with HBr to afford an alkyl bromide. Based on their structures, indicate if the reaction mechanism is likely to be Sn1 or Sn2arrow_forwardThe rate law for addition of Br2 to an alkenes is first order in Br2 and first order in the alkene. Does this information suggest that the mechanism of addition of Br2 to an alkene proceeds in the same matter as for addition of HBr? Explain.arrow_forward
- When (1-bromoethyl)cyclohexane is heated in methanol for an extended period of time, five products result: two ethers and three alkenes. Predict the products of this reaction, and propose mechanisms for their formation. Predict which of the three alkenes is the major elimination productarrow_forwardReaction of iodoethane with CN- yields a small amount of isonitrile, CH3CH2N≡C, along with the nitrile CH3CH2N≡N, as the major product. Write electron-dot structures for both products, assign formal charges as necessary, and propose mechanisms to account for their formation.arrow_forward
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