Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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
A task is assigned to an undergraduate student to test two samples (known as
compounds K and L) in the laboratory. She placed these two compounds through
various scientific tests. She discovered that these compounds have the same
molecular formula, CSHSO. When treated with 2,4-dinitrophenylhydrazine, all of
these compounds produce brightly coloured precipitate, and both are reduced to an
organic compound with the molecular formula C§H100. However, compound K can
be easily oxidized by chromic acid to formed compound N and vice versa for
compound L. Furthermore, when both compounds react with Fehling's solutions,
they produce negative results. However, only compound K forms a silver mirror
when it reacts with Tollen's reagent, and compound L does not.
Identify the possible structural formulae for compounds K, L, and N by ignoring
their position isomerism.
Indicate the formation of compound N from compound K.
Predict the chemical reaction that occurs when compound L reacts with 2,4-…
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?
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)
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 - A compound (N) with the molecular formula C9H10O...Ch. 14 - The IR and 1H NMR spectra for compound X(C8H10)...Ch. 14 - Prob. 38PCh. 14 - Prob. 39PCh. 14 - 14.39 Given the following information, predict the...Ch. 14 - Consider these reactions: The intermediate A is a...Ch. 14 - Prob. 42PCh. 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. 5LGPCh. 14 - Prob. 1QCh. 14 - Which is the correct name of the compound shown?...Ch. 14 - Prob. 3QCh. 14 - Prob. 4QCh. 14 - Give the structure of a compound with the formula...Ch. 14 - Prob. 6Q
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