Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 8.SE, Problem 38MP
Reaction of cyclohexene with mercury(II) acetate in CH3OH rather than H2O, followed by treatment with NaBH4, yields cyclohexyl methyl ether rather than cyclohexanol. Suggest a mechanism.
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Chapter 8 Solutions
Organic Chemistry
Ch. 8.1 - Prob. 1PCh. 8.1 - How many alkene products, including E,Z isomers,...Ch. 8.2 - Prob. 3PCh. 8.2 - Addition of HCl to 1, 2-dimethylcyclohexene yields...Ch. 8.3 - Prob. 5PCh. 8.3 - Prob. 6PCh. 8.4 - Prob. 7PCh. 8.4 - From what alkenes might the following alcohols...Ch. 8.5 - Prob. 9PCh. 8.5 - What alkenes might be used to prepare the...
Ch. 8.5 - Tho following cycloalkene gives a mixture of two...Ch. 8.6 - Prob. 12PCh. 8.7 - Prob. 13PCh. 8.7 - Starting with an alkene, how would you prepare...Ch. 8.8 - Prob. 15PCh. 8.8 - Prob. 16PCh. 8.9 - What products would you expect from the following...Ch. 8.10 - Prob. 18PCh. 8.10 - Prob. 19PCh. 8.13 - Prob. 20PCh. 8.13 - What products are formed from hydration of...Ch. 8.SE - Name the following alkenes, and predict the...Ch. 8.SE - Prob. 23VCCh. 8.SE - Prob. 24VCCh. 8.SE - Prob. 25VCCh. 8.SE - Prob. 26MPCh. 8.SE - Prob. 27MPCh. 8.SE - Draw the structures of the organoboranes formed...Ch. 8.SE - Prob. 29MPCh. 8.SE - Provide the mechanism and products for the...Ch. 8.SE - Propose a curved-arrow mechanism to show how ozone...Ch. 8.SE - Prob. 32MPCh. 8.SE - Prob. 33MPCh. 8.SE - Prob. 34MPCh. 8.SE - 10-Bromo- α -chamigrene, a compound isolated from...Ch. 8.SE - Isolated from marine algae, prelaureatin is...Ch. 8.SE - Dichlorocarbene can be generated by heating sodium...Ch. 8.SE - Reaction of cyclohexene with mercury(II) acetate...Ch. 8.SE - Use your general knowledge of alkene chemistry to...Ch. 8.SE - Prob. 40MPCh. 8.SE - Hydroboration of 2-methyl-2-pentene at 25°C,...Ch. 8.SE - Prob. 42APCh. 8.SE - Suggest structures for alkenes that give the...Ch. 8.SE - Prob. 44APCh. 8.SE - Prob. 45APCh. 8.SE - Prob. 46APCh. 8.SE - Prob. 47APCh. 8.SE - Predict the products of the following reactions....Ch. 8.SE - Prob. 49APCh. 8.SE - How would you carry out the following...Ch. 8.SE - Draw the structure of an alkene that yields only...Ch. 8.SE - Show the structures of alkenes that give the...Ch. 8.SE - Prob. 53APCh. 8.SE - Which of the following alcohols could not be made...Ch. 8.SE - Prob. 55APCh. 8.SE - Prob. 56APCh. 8.SE - Prob. 57APCh. 8.SE - Compound A has the formula C10HI6. On catalytic...Ch. 8.SE - Prob. 59APCh. 8.SE - Prob. 60APCh. 8.SE - Prob. 61APCh. 8.SE - Draw the structure of a hydrocarbon that absorbs 2...Ch. 8.SE - Prob. 63APCh. 8.SE - The sex attractant of the common housefly is a...Ch. 8.SE - Prob. 65APCh. 8.SE - Prob. 66APCh. 8.SE - α-Terpinene, C10H16, is a pleasant-smelling...Ch. 8.SE - Prob. 68APCh. 8.SE - Prob. 69APCh. 8.SE - Prob. 70APCh. 8.SE - Prob. 71APCh. 8.SE - Prob. 72AP
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- When cis-4-chlorocyclohexanol is treated with sodium hydroxide in ethanol, it gives mainly the substitution product trans-1,4-cyclohexanediol (1). Under the same reaction conditions, trans-4-chlorocyclohexanol gives 3-cyclohexenol (2) and the bicyclic ether (3). (a) Propose a mechanism for formation of product (1), and account for its configuration. (b) Propose a mechanism for formation of product (2). (c) Account for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forwardHydroboration of 2-methyl-2-pentene at 25°C, followed by oxidation with alkaline H2O2, yields 2-methyl-3-pentanol, but hydroboration at 160°C followed by oxidation yields 4- methyl-l-pentanol. Suggest a mechanism.arrow_forwardPropose a mechanism for the acid-catalyzed hydration of methylidenecyclohexane to give 1-methylcyclohexanol. Which step in your mechanism is rate-determining?arrow_forward
- Based on what you know about the relative stabilities of alkyl radicals and benzylic radicals, predict the product of addition of HBr to 1-phenylpropene in the presence of a free-radical initiator. Propose a mechanism for this reaction.arrow_forwardTreating 1-methyl-1-vinylcyclopentane with HCl gives mainly 1-chloro-1,2-dimethylcyclohexane. Propose a mechanism for the formation of this product.arrow_forwardPropose a mechanism for addition of HI to 1-methylcyclohexene to give 1-iodo1-methylcyclohexane. Which step in your mechanism is rate-determining?arrow_forward
- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardBicyclo-2,5-heptadiene can be prepared in two steps from cyclopentadiene and vinyl chloride. Provide a mechanism for each step.arrow_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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