EBK ORGANIC CHEMISTRY
9th Edition
ISBN: 9780100591318
Author: McMurry
Publisher: YUZU
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Chapter 3.SE, Problem 52AP
Increased substitution around a bond leads to increased strain. Take the four substituted butanes listed below, for example. For each compound, sight along the C2-C3 bond and draw Newman projections of the most stable and least stable conformations. Use the data in Table 3-5 to assign strain-energy values to each conformation. Which of the eight conformations is most strained? Which is least strained?
(a) 2-Methylbutane
(b) 2,2-Dimethylbutane
(c) 2,3-Dimethylbutane
(d) 2,2,3-Trimethylbutane
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Consider the "C NMR spectrum below.
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The structure of compound 1,3,5-trimethylbenzene (mesitylene) is given below.
How many signals would you expect to find in the 'H NMR spectrum of 1,3,5-trimethylbenzene (mesitylene)?
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How many signals do you expect in the 'H NMR spectrum for this molecule?
CI CI
Cl
Write the answer in the table below.
Also, in each of the drawing areas below is a copy of the molecule, with H atoms shown. In each copy, one of the H atoms is highlighted red. Highlight in red all
other H atoms that would contribute to the same signal as the H already highlighted red.
Note for advanced students: Remember, a multiplet is considered one signal in the 'H NMR spectrum.
1
Number of signals in the 'H NMR spectrum.
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For the molecule in the top drawing area, highlight in red any other H atoms that will contribute to the same
signal as the H atom already highlighted red.
If no other H atoms will contribute, check the box at right.
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top molecule
For the molecule in the bottom drawing area, highlight in red any other H atoms that will contribute to the
same signal as the H atom already highlighted red.
If no other H atoms will contribute, check the box at…
Chapter 3 Solutions
EBK ORGANIC CHEMISTRY
Ch. 3.1 - Prob. 1PCh. 3.1 - Prob. 2PCh. 3.1 - Identify the functional groups in the following...Ch. 3.2 - Draw structures of the five isomers of C6H14.Ch. 3.2 - Propose structures that meet the following...Ch. 3.2 - Prob. 6PCh. 3.3 - Draw the eight 5-carbon alkyl groups (pentyl...Ch. 3.3 - Identify the carbon atoms in the following...Ch. 3.3 - Prob. 9PCh. 3.3 - Prob. 10P
Ch. 3.4 - Give IUPAC names for the following compounds:Ch. 3.4 - Prob. 12PCh. 3.4 - Name the eight 5-carbon alkyl groups you drew in...Ch. 3.4 - Give the IUPAC name for the following hydrocarbon,...Ch. 3.7 - Make a graph of potential energy versus angle of...Ch. 3.7 - Sight along the C2-C1 bond of 2-methylpropane...Ch. 3.7 - Sight along the C2-C3 bond of 2,3-dimethylbutane,...Ch. 3.7 - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 19VCCh. 3.SE - Prob. 20VCCh. 3.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 3.SE - Prob. 22APCh. 3.SE - Prob. 23APCh. 3.SE - Propose structures for the following: (a) A...Ch. 3.SE - Prob. 25APCh. 3.SE - Draw the structures of the following molecules:...Ch. 3.SE - Draw structures that meet the following...Ch. 3.SE - Prob. 28APCh. 3.SE - In each of the following sets, which structures...Ch. 3.SE - There are seven constitutional isomers with the...Ch. 3.SE - Prob. 31APCh. 3.SE - Draw compounds that contain the following: (a) A...Ch. 3.SE - Prob. 33APCh. 3.SE - Draw and name all monochloro derivatives of...Ch. 3.SE - Draw structures for the following: (a)...Ch. 3.SE - Prob. 36APCh. 3.SE - Draw a compound that: (a) Has nine primary...Ch. 3.SE - Give IUPAC names for the following compounds:Ch. 3.SE - Name the five isomers of C6H14.Ch. 3.SE - Explain why each of the following names is...Ch. 3.SE - Prob. 41APCh. 3.SE - Consider 2-methylbutane (isopentane). Sighting...Ch. 3.SE - What are the relative energies of the three...Ch. 3.SE - Construct a qualitative potential-energy diagram...Ch. 3.SE - Prob. 45APCh. 3.SE - Draw the most stable conformation of pentane,...Ch. 3.SE - Draw the most stable conformation of...Ch. 3.SE - Prob. 48APCh. 3.SE - Prob. 49APCh. 3.SE - Formaldehyde, H2C=O, is known to all biologists...Ch. 3.SE - Prob. 51APCh. 3.SE - Increased substitution around a bond leads to...Ch. 3.SE - Prob. 53APCh. 3.SE - In the next chapter we'll look at...Ch. 3.SE - We’ll see in the next chapter that there are two...
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