Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Question
Chapter 14, Problem 1LGP
Interpretation Introduction
Interpretation:
The mechanism arrows for given reaction is to be written and the transformation is a reasonable process is to be explained.
Concept introduction:
The removal of alcohol group occurs by the addition of hydrogen ion, followed by the removal of one water molecule.
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Students have asked these similar questions
5. Optically pure 2-octyl sulfonate was treated with varying mixtures of water and dioxane, and the
optical purity of the resulting product (2-octanol) was found to vary with the ratio of water to
dioxane, as shown in the following table (J. Am. Chem. Soc. 1965, 87, 287-291). Given that
dioxane possesses fairly nucleophilic oxygen atoms, provide a complete mechanism that
explains the variation in in the product's optical purity due to changes in solvent composition.
Hint, the solvent is doing more here than just dissolving.. it is partaking in the reaction.
Solvent Ratio (water : dioxane)
25:75
50: 50
75: 25
100 :0
Optical purity of (S)-2-octanol
77%
88%
95%
100%
H20
он
(R)-2-Octyl sulfonate
(optically pure)
(S)-2-Octanol
(dioxane)
Treatment of 1,3,6-cyclononatriene (Compound 1), or its dimethyl derivative (Compound 2), with potassium amide (KNH₂) in liquid
ammonia results in the formation of anion 1a or 2a, respectively (J. Am. Chem. Soc. 1973, 95, 3437-3438):
9
15.85a
2
6
3
4
5
Compound 1
(R=H)
Compound 2
(R=CH3)
* You answer is incorrect.
KNH₂
KNH₂
1a
(anion)
2a
(anion)
Of the following, which is NOT one of the four resonance structures of 1a?
Write the mechanism, as well as the structure of intermediate A and product B, for the following reaction.
Chapter 14 Solutions
Organic Chemistry
Ch. 14 - PRACTICE PROBLEM 14.1 Provide a name for each of...Ch. 14 - Prob. 2PPCh. 14 - Prob. 3PPCh. 14 - Practice Problem 14.4 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.5 Apply the polygon-and-circle...Ch. 14 - Practice Problem 14.6 1,3,5-Cycloheptatriene is...Ch. 14 - Prob. 7PPCh. 14 - Prob. 8PPCh. 14 - Practice Problem 14.9 In 1967 R. Breslow (of...Ch. 14 - Prob. 10PP
Ch. 14 - Practice Problem 14.11 In addition to a signal...Ch. 14 - PRACTICE PROBLEM 14.12
Azulene has an appreciable...Ch. 14 - Practice Problem 14.13 (a) The -Sh group is...Ch. 14 - Practice Problem 14.14
Explain how NMR...Ch. 14 - PRACTICE PROBLEM 14.15 Four benzenoid compounds,...Ch. 14 - Prob. 16PCh. 14 - Write structural formulas and give acceptable...Ch. 14 - Prob. 18PCh. 14 - Prob. 19PCh. 14 - Prob. 20PCh. 14 - Which of the hydrogen atoms shown below is more...Ch. 14 - 14.22 The rings below are joined by a double bond...Ch. 14 - Prob. 23PCh. 14 - 14.24 (a) In 1960 T. Katz (Columbia University)...Ch. 14 - Prob. 25PCh. 14 - Prob. 26PCh. 14 - 14.27 5-Chloro-1,3-cyclopentadiene (below)...Ch. 14 - Prob. 28PCh. 14 - Furan possesses less aromatic character than...Ch. 14 - 14.30 For each of the pairs below, predict...Ch. 14 - Assign structures to each of the compounds A, B,...Ch. 14 - Prob. 32PCh. 14 - Give a structure for compound F that is consistent...Ch. 14 - Prob. 34PCh. 14 - Prob. 35PCh. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 37PCh. 14 - Prob. 38PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 41PCh. 14 - Compound E has the spectral features given below....Ch. 14 - Draw all of the molecular orbitals for...Ch. 14 - Prob. 1LGPCh. 14 - Prob. 2LGPCh. 14 - 3. The NMR signals for the aromatic hydrogens of...Ch. 14 - Prob. 4LGPCh. 14 - Prob. 5LGP
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