Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Textbook Question
Chapter 18.9, Problem 18P
The 1H NMR spectrum shown is that of a cyclic ether with the formula C4H8O. Propose a structure.
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Check the box under each structure in the table that is an enantiomer of the molecule shown below. If none of them are, check the none of the above box under
the table.
Molecule 1
Molecule 2
IZ
IN
Molecule 4
Molecule 5
ZI
none of the above
☐
Molecule 3
Х
IN
www
Molecule 6
NH
G
Highlight each chiral center in the following molecule. If there are none, then check the box under the drawing area.
There are no chiral centers.
Cl
Cl
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A student proposes the following two-step synthesis of an ether from an alcohol A:
1. strong base
A
2. R
Is the student's proposed synthesis likely to work?
If you said the proposed synthesis would work, enter the chemical
formula or common abbreviation for an appropriate strong base to use
in Step 1:
If you said the synthesis would work, draw the structure of an alcohol
A, and the structure of the additional reagent R needed in Step 2, in
the drawing area below.
If there's more than one reasonable choice for a good reaction yield,
you can draw any of them.
☐
Click and drag to start drawing a structure.
Yes
No
ロ→ロ
0|0
G
Х
D
: ☐
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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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- टे Predict the major products of this organic reaction. Be sure to use wedge and dash bonds when necessary, for example to distinguish between different major products. ☐ ☐ : ☐ + NaOH HO 2 Click and drag to start drawing a structure.arrow_forwardShown below are five NMR spectra for five different C6H10O2 compounds. For each spectrum, draw the structure of the compound, and assign the spectrum by labeling H's in your structure (or in a second drawing of the structure) with the chemical shifts of the corresponding signals (which can be estimated to nearest 0.1 ppm). IR information is also provided. As a reminder, a peak near 1700 cm-1 is consistent with the presence of a carbonyl (C=O), and a peak near 3300 cm-1 is consistent with the presence of an O–H. Extra information: For C6H10O2 , there must be either 2 double bonds, or 1 triple bond, or two rings to account for the unsaturation. There is no two rings for this problem. A strong band was observed in the IR at 1717 cm-1arrow_forwardPredict the major products of the organic reaction below. : ☐ + Х ك OH 1. NaH 2. CH₂Br Click and drag to start drawing a structure.arrow_forward
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