Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
9th Edition
ISBN: 9781305780170
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 18.3, Problem 9P
Why are HI and HBr more effective than HCl in cleaving ethers? (See Section 11-3.)
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What qualifies as a good ether solvent?
1. In the reactions involving the three isomeric alcohols with the formula C4H9OH, describewhat each of the following tests showed about reactivity of the -OH group and reactions of 1°,2°, and 3° alcohols.• the test with neutral KMnO4• the test with concentrated HCl2. Predict how the fourth alcohol with the formula C4H10O would react if tested with:• 0.01 M KMnO4• concentrated HCl at room temperatureExtend FurtherUse your observations of the solutions formed in the previous experiments and yourunderstanding of alcohols to complete a table like the one shown below. Research the meltingand boiling points to verify your answers.
which of the following solvents will NOT dissolve 1-hexene?
diethyl ether, hexane, concentrated sulphuric acid, 5% NaHCO3
Chapter 18 Solutions
Bundle: Organic Chemistry, Loose-leaf Version, 9th + LMS Integrated for OWLv2, 4 terms (24 months) Printed Access Card
Ch. 18.1 - Name the following ethers:Ch. 18.2 - Why do you suppose only symmetrical ethers are...Ch. 18.2 - How would you prepare the following ethers using a...Ch. 18.2 - Review the mechanism of oxymercuration shown in...Ch. 18.2 - How would you prepare the following ethers? Use...Ch. 18.2 - Prob. 6PCh. 18.3 - Prob. 7PCh. 18.3 - Write the mechanism of the acid-induced cleavage...Ch. 18.3 - Why are HI and HBr more effective than HCl in...Ch. 18.4 - What product would you expect from Claisen...
Ch. 18.5 - Prob. 11PCh. 18.6 - Predict the major product of each of the following...Ch. 18.6 - Prob. 13PCh. 18.6 - Predict the major product of the following...Ch. 18.7 - 15-Crown-5 and 12-crown-4 ethers complex Na+ and...Ch. 18.8 - Prob. 16PCh. 18.8 - 2-Butene-l-thiol is one component of skunk spray....Ch. 18.9 - The 1H NMR spectrum shown is that of a cyclic...Ch. 18.SE - Give IUPAC names for the following compounds...Ch. 18.SE - Show the product, including stereochemistry, that...Ch. 18.SE - Prob. 21VCCh. 18.SE - Treatment of the following alkene with a...Ch. 18.SE - Prob. 23MPCh. 18.SE - Prob. 24MPCh. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - The alkoxymercuration of alkenes involves the...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Predict the product(s) and provide the mechanism...Ch. 18.SE - Prob. 29MPCh. 18.SE - Ethers undergo an acid-catalyzed cleavage reaction...Ch. 18.SE - Treatment of 1, 1-diphenyl-l, 2-epoxyethane with...Ch. 18.SE - Fluoxetine, a heavily prescribed antidepressant...Ch. 18.SE - When 2-methyl-2, 5-pentanediol is treated with...Ch. 18.SE - Prob. 34MPCh. 18.SE - Prob. 35MPCh. 18.SE - Aldehydes and ketones undergo acid-catalyzed...Ch. 18.SE - Propose a mechanism to account for the following...Ch. 18.SE - Prob. 38APCh. 18.SE - Prob. 39APCh. 18.SE - How would you prepare the following ethers?Ch. 18.SE - Prob. 41APCh. 18.SE - tert-Butyl ethers can be prepared by the reaction...Ch. 18.SE - Treatment of trans-2-chlorocyclohexanol with NaOH...Ch. 18.SE - Predict the products of the following ether...Ch. 18.SE - Prob. 45APCh. 18.SE - Prob. 46APCh. 18.SE - Write the mechanism of the hydrolysis of cis-5,...Ch. 18.SE - Prob. 48APCh. 18.SE - Acid-catalyzed hydrolysis of a 1,...Ch. 18.SE - Prob. 50APCh. 18.SE - Epoxides are reduced by treatment with lithium...Ch. 18.SE - Prob. 52APCh. 18.SE - The red fox (Vulpes vulpes) uses a chemical...Ch. 18.SE - Anethole, C10H12O, a major constituent of the oil...Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 56GPCh. 18.SE - How would you synthesize anethole (Problem 18-54)...Ch. 18.SE - How could you prepare benzyl phenyl ether from...Ch. 18.SE - Meerwein's reagent, triethyloxonium...Ch. 18.SE - Prob. 60GPCh. 18.SE - Prob. 61GPCh. 18.SE - The Zeisel method is an old analytical procedure...Ch. 18.SE - Prob. 63GPCh. 18.SE - Prob. 64GPCh. 18.SE - Prob. 65GPCh. 18.SE - Identify the reagents a-e in the following scheme:Ch. 18.SE - Propose structures for compounds that have the...Ch. 18.SE - Prob. 68GPCh. 18.SE - Prob. 69GPCh. 18.SE - Predict the product(s) if the starting materials...
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- 17-26 Account for the fact that acetone has a higher boiling point (56°C) than ethyl methyl ether (11°C) even though their molecular weights are almost the same.arrow_forwardDissolving formaldehyde in water causes the solution to contain gem-diol CH2 (OH)2. Write down the steps for the formation of formaldehyde.arrow_forwardbutene-1 acts on a combination of three reactants.Write the corresponding reactions. a) H2, Br2, N2 b) Na, NaOH, HCl c) H2O, HBr, KMnO4 d) Cl2, CO2, H2SO4arrow_forward
- Besides water, what is being removed from the ether layer when it is washed with a saturated NaCl solution?arrow_forwardAccount the solubility of carboxylic acids in distilled waterarrow_forwardFigure 13.13 focuses on the use of thiol chemistry by skunks. If thiols are more volatile than alcohols and less soluble in water, why do these properties represent an advantage to skunks?arrow_forward
- Starting with 1-butanol, provide a synthetic scheme to make 4-methyl-4 hexanol, including intermediate products.arrow_forwardWrite the equations involved in the following reactions:(i) Williamson ether synthesis(ii) Kolbe’s reactionarrow_forwardWhat is the function of CH2Cl2 in the bromination reactions? Why can it fulfil this rolearrow_forward
- In the reactions involving 1-butanol, 2-butanol and 2-methyl-2-propanol with the formula C4H9OHdescribe what each of the following tests showed about the reactivity of the -OH group and reactions of 1°,2°, and 3° alcohols. The test with neutral KMnO4 The test with concentrated HClarrow_forward14-64 Explain why the boiling point of ethylene glycol (198°C) is so much higher than that of 1-propanol (97°C), even though their molecular weights are about the same.arrow_forwardAccount for the fact that the bicyclic ether (3) is formed from the trans isomer but not from the cis isomer.arrow_forward
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