Organic Chemistry
8th Edition
ISBN: 9781305580350
Author: William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher: Cengage Learning
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Textbook Question
Chapter 13.7, Problem 13.5P
Following are two constitutional isomers with the molecular formula C4H8O2.
- (a) Predict the number of signals in the 1H-NMR spectrum of each isomer.
- (b) Predict the ratio of areas of the signals in each spectrum.
- (c) Show how you can distinguish between these isomers on the basis of chemical shift.
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You are trying to decide if there is a single reagent you can add that will make the following synthesis possible without any other major side products:
xi
1. ☑
2. H₂O
хе
i
Draw the missing reagent X you think will make this synthesis work in the drawing area below.
If there is no reagent that will make your desired product in good yield or without complications, just check the box under the drawing area and leave it blank.
Click and drag to start drawing a
structure.
There is no reagent that will make this synthesis work without complications.
: ☐
S
☐
Predict the major products of this organic reaction:
H
OH
1. LiAlH4
2. H₂O
?
Note: be sure you use dash and wedge bonds when necessary, for example to distinguish between major products with different stereochemistry.
Click and drag to start drawing a
structure.
G
C
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For each reaction below, decide if the first stable organic product that forms in solution will create a new C-C bond, and check the appropriate box.
Next, for each reaction to which you answered "Yes" to in the table, draw this product in the drawing area below.
Note for advanced students: for this problem, don't worry if you think this product will continue to react under the current conditions - just focus on the first
stable product you expect to form in solution.
NH2
CI
MgCl
?
Will the first product that forms in this reaction
create a new CC bond?
Yes
No
MgBr
?
Will the first product that forms in this reaction
create a new CC bond?
Yes
No
G
टे
Chapter 13 Solutions
Organic Chemistry
Ch. 13.2 - Calculate the ratio of nuclei in the higher spin...Ch. 13.5 - State the number of sets of equivalent hydrogens...Ch. 13.5 - Each compound gives only one signal in its 1H-NMR...Ch. 13.6 - The line of integration of the two signals in the...Ch. 13.7 - Following are two constitutional isomers with the...Ch. 13.8 - Following are pairs of constitutional isomers....Ch. 13.10 - Following is a 1H-NMR spectrum of 2-butanol....Ch. 13.11 - Explain how to distinguish between the members of...Ch. 13 - Prob. 13.9PCh. 13 - Prob. 13.10P
Ch. 13 - Prob. 13.11PCh. 13 - Following are structural formulas for three...Ch. 13 - Following arc structural formulas for the cis...Ch. 13 - Prob. 13.14PCh. 13 - Following are three compounds with the molecular...Ch. 13 - Following are 1H-NMR spectra for compounds D, E,...Ch. 13 - Following are 1H-NMR spectra for compounds G, H,...Ch. 13 - Propose a structural formula for compound J,...Ch. 13 - Compound K, molecular formula C6H14O, readily...Ch. 13 - Compound M, molecular formula C5H10O, readily...Ch. 13 - Following is the 1H-NMR spectrum of compound O,...Ch. 13 - Treatment of compound P with BH3 followed by...Ch. 13 - The 1H-NMR spectrum of compound R, C6H14O,...Ch. 13 - Write structural formulas for the following...Ch. 13 - Prob. 13.25PCh. 13 - Ascaridole is a natural product that has been used...Ch. 13 - The 13C-NMR spectrum of 3-methyl-2-butanol shows...Ch. 13 - Prob. 13.28P
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