Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18.3, Problem 9P
Why are HI and HBr more effective than HCl in cleaving ethers? (See Section 11-3.)
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
How many grams of NaBH4 are needed to reduce 13.75 g of a ketone with molar mass 152.24 g/mol such that there are 1.53 equivalents of hydride?
You have been tasked to assess a new laboratory for safety issues. The lab has a large amount of benzene, hydrochloric acid, phenol, sodium hydroxide and toluene. Describe the (5) potential hazards that can be associated with each chemical above, as well as the methods to control their potential hazards in the lab.
Safety data Sheet and Store requirements for each product in a production of ISOPHORONE.
Raw Material
Acetone
Calcium Carbide (CaC2 )
Water
Product
Isophorone
By Product
Acetylene
Calcium Hydroxide [Ca(OH)2]
Chapter 18 Solutions
Organic Chemistry
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...
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 10-28 List three reasons why functional groups are important in organic chemistry.arrow_forward17-27 Pentane, 1-butanol, and butanal all have approximately the same molecular weights but different boiling points. Arrange them in order of increasing boiling point. Explain the basis for your ranking.arrow_forwardThe disinfection of drinking water to control microbial contaminants can form chemical disinfection byproducts. These compounds result from the reaction of chlorine with naturally occurring organic matter (the dissolved molecules that give natural water the yellow-greenish color). One class of disinfection byproducts is the malodorous and unpalatable chlorophenols. 2,4-dichlorophenol is one compound of this class. a) Calculate the vapor pressure p*L of 2,4-dichlorophenol at 60 °C using Tb and structural information only OH .CI M, = 163.0 g/mol Tm = 43.7 °C Tp = 213.0°C %3D %3D %3Darrow_forward
- Which is the most soluble in water? NaCl CH3CH3 CH3OCH3 CH3OHarrow_forwardWhy are the interactions between H2O molecules stronger than those between HF molecules, even though the polarity of the HF bond is larger than the polarity of the OH bond?arrow_forwardDraw structural formulas for organic products A and B in the window below. Mg A H20 B H3CC=CH2 ether Brarrow_forward
- How can we predict if 1- propanol is mixed with distilled water? Are the mass and volume conserved? When you mix two gases what can we predict about the conservation of volume in this case?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_forwardWhy is water more acidic than ethanol but slightly less acidic than methanol?arrow_forward
- Please write a balanced reaction between benzhydrol (diphenylmethanol) and NaHCO3.arrow_forwardOxidation and Reduction of Aldehydes and Ketones (Section 15-10) 15-75 Draw the structural formula of the carboxylic acid formed when each of the following aldehydes is oxidized. a. CH,-C-H CH3 b. CH;-CH,-ČH-CH,-C-H с. Н-С—Н ÇI ÇI d. CH;—CH,—CH-CH—CH2—С-нarrow_forwardWhich of the following can dissolve in water? (Give all answers) O butane O 1-butanol CH3CH3 HOCH2CH2CH,CH2OH none of the compounds can dissolve in waterarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Introduction to General, Organic and BiochemistryChemistryISBN:9781285869759Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar TorresPublisher:Cengage Learning
Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co
Chemistry & Chemical ReactivityChemistryISBN:9781133949640Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Chemistry & Chemical ReactivityChemistryISBN:9781337399074Author:John C. Kotz, Paul M. Treichel, John Townsend, David TreichelPublisher:Cengage Learning
Introduction to General, Organic and Biochemistry
Chemistry
ISBN:9781285869759
Author:Frederick A. Bettelheim, William H. Brown, Mary K. Campbell, Shawn O. Farrell, Omar Torres
Publisher:Cengage Learning
Chemistry: Matter and Change
Chemistry
ISBN:9780078746376
Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl Wistrom
Publisher:Glencoe/McGraw-Hill School Pub Co
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781133949640
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Chemistry & Chemical Reactivity
Chemistry
ISBN:9781337399074
Author:John C. Kotz, Paul M. Treichel, John Townsend, David Treichel
Publisher:Cengage Learning
Alcohols, Ethers, and Epoxides: Crash Course Organic Chemistry #24; Author: Crash Course;https://www.youtube.com/watch?v=j04zMFwDeDU;License: Standard YouTube License, CC-BY