Organic Chemistry
9th Edition
ISBN: 9781305080485
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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Consider the structure of 1-bromo-2-fluoroethane.
Part 1 of 2
Draw the Newman projection for the anti conformation of 1-bromo-2-fluoroethane, viewed down the C1-C2 bond.
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ぬ
Part 2 of 2
H
H
F
Br
H
H
☑
Draw the Newman projection for the gauche conformation of 1-bromo-2-fluoroethane, viewed down the C1-C2 bond.
H
F
Br
H
H
Please help me answer this question. I don't understand how or where the different reagents will attach and it's mostly due to the wedge bond because I haven't seen a problem like this before. Please provide a detailed explanation and a drawing showing how it can happen and what the final product will look like.
Which of the following compounds is the most acidic in the gas phase?
Group of answer choices
H2O
SiH4
HBr
H2S
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...
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- Which of the following is the most acidic transition metal cation? Group of answer choices Fe3+ Sc3+ Mn4+ Zn2+arrow_forwardBased on the thermodynamics of acetic acid dissociation discussed in Lecture 2-5, what can you conclude about the standard enthalpy change (ΔHo) of acid dissociation for HCl? Group of answer choices You cannot arrive at any of the other three conclusions It is a positive value It is more negative than −0.4 kJ/mol It equals −0.4 kJ/molarrow_forwardPLEASE HELP URGENT!arrow_forward
- Draw the skeletal structure corresponding to the following IUPAC name: 7-isopropyl-3-methyldecanearrow_forwardWhich of the following oxyacids is the weakest? Group of answer choices H2SeO3 Si(OH)4 H2SO4 H3PO4arrow_forwardAdd conditions above and below the arrow that turn the reactant below into the product below in a single transformation. + More... If you need to write reagents above and below the arrow that have complex hydrocarbon groups in them, there is a set of standard abbreviations you can use. More... T H,N NC Datarrow_forward
- Indicate the order of basicity of primary, secondary and tertiary amines.arrow_forward> Classify each of the following molecules as aromatic, antiaromatic, or nonaromatic. Cl Z- N O aromatic O antiaromatic O nonaromatic O aromatic O antiaromatic O nonaromatic O aromatic ○ antiaromatic nonaromaticarrow_forwardPlease help me answer this question. I don't understand how or even if this can happen in a single transformation. Please provide a detailed explanation and a drawing showing how it can happen in a single transformation. Add the necessary reagents and reaction conditions above and below the arrow in this organic reaction. If the products can't be made from the reactant with a single transformation, check the box under the drawing area instead.arrow_forward
- 2) Draw the correct chemical structure (using line-angle drawings / "line structures") from their given IUPAC name: a. (E)-1-chloro-3,4,5-trimethylhex-2-ene b. (Z)-4,5,7-trimethyloct-4-en-2-ol C. (2E,6Z)-4-methylocta-2,6-dienearrow_forwardපිපිම Draw curved arrows to represent the flow of electrons in the reaction on the left Label the reactants on the left as either "Acid" or "Base" (iii) Decide which direction the equilibrium arrows will point in each reaction, based on the given pk, values (a) + H-O H 3-H + (c) H" H + H****H 000 44-00 NH₂ (e) i Дон OH Ө NHarrow_forward3) Label the configuration in each of the following alkenes as E, Z, or N/A (for non-stereogenic centers). 00 E 000 N/A E Br N/A N/A (g) E N/A OH E (b) Oz N/A Br (d) 00 E Z N/A E (f) Oz N/A E (h) Z N/Aarrow_forward
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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