
Student's Solutions Manual for Organic Chemistry
9th Edition
ISBN: 9780134160375
Author: Leroy G. Wade, Jan W. Simek
Publisher: PEARSON
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Textbook Question
Chapter 12, Problem 12.23SP
An unknown, foul-smelling hydrocarbon gives the mass spectrum and infrared spectrum shown.
- a. Use the mass spectrum to propose a molecular formula. How many elements of unsaturation are there?
- b. Use the IR spectrum to determine the
functional group (s), if any. - c. Propose one or more structures for this compound. What parts of the structure are uncertain? If you knew that hydrogenation of the compound gives n-octane, would the structure still be uncertain?
- d. Propose structures for the major fragments at 39, 67, 81, and 95 in the mass spectrum.
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Can the molecule on the right-hand side of this organic reaction be made in good yield from no more than two reactants, in one
step, by moderately heating the reactants?
?
Δ
• If your answer is yes, then draw the reactant or reactants in the drawing area below. You can draw the reactants in any
arrangement you like.
If your answer is no, check the box under the drawing area instead.
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Predict the major products of the following organic reaction:
O O
+
A
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Some important notes:
• Draw the major product, or products, of the reaction in the drawing area below.
• If there aren't any products, because no reaction will take place, check the box below the drawing area instead.
• Be sure to use wedge and dash bonds when necessary, for example to distinguish between major products that are
enantiomers.
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Chapter 12 Solutions
Student's Solutions Manual for Organic Chemistry
Ch. 12.3 - Complete the following conversion table. (cm1)...Ch. 12.5 - Which of the bonds shown in red are expected to...Ch. 12.7C - For each hydrocarbon spectrum, determine whether...Ch. 12.9A - Spectra are given for three compounds. Each...Ch. 12.10 - The infrared spectra for three compounds are...Ch. 12.12 - Prob. 12.6PCh. 12.14B - Identify which of these four mass spectra indicate...Ch. 12.15A - Show the fragmentation that accounts for the...Ch. 12.15A - Show the fragmentations that give rise to the...Ch. 12.15B - Ethers are not easily differentiated by their...
Ch. 12.15C - Prob. 12.11PCh. 12 - Prob. 12.12SPCh. 12 - Prob. 12.13SPCh. 12 - All of the following compounds absorb infrared...Ch. 12 - Prob. 12.15SPCh. 12 - Four infrared spectra are shown, corresponding to...Ch. 12 - Predict the masses and the structures of the most...Ch. 12 - Prob. 12.18SPCh. 12 - Prob. 12.19SPCh. 12 - (A true story) While organizing the undergraduate...Ch. 12 - Prob. 12.21SPCh. 12 - Prob. 12.22SPCh. 12 - An unknown, foul-smelling hydrocarbon gives the...Ch. 12 - covered a synthesis of alkynes by a double...Ch. 12 - Three IR spectra are shown, corresponding to three...Ch. 12 - Prob. 12.26SPCh. 12 - Prob. 12.27SPCh. 12 - Prob. 12.28SPCh. 12 - The ultimate test of fluency in MS and IR is...Ch. 12 - Prob. 12.30SPCh. 12 - Consider the following four structures, followed...
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