EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
9th Edition
ISBN: 9780136781776
Author: Wade
Publisher: PEARSON CO
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Chapter 25, Problem 25.28SP
Interpretation Introduction
Interpretation: The structure of petroselenic acid and its consistency with the given observations is to be stated.
Concept introduction: The hydrogenation reaction convert an
The reaction of an
The protons that are attached directly to an alkene is called vinylic protons. The NMR spectrum shows absorption of vinylic protons split by coupling constant (that are cis to each other) in the range of
To determine: The structure of petroselenic acid and its consistency with the given observations.
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When an extract of parsley seed is saponified and acidified, one of the fatty acids isolated is petroselenic acid, formulaC18H34O2. Hydrogenation of petroselenic acid gives pure stearic acid. When petroselenic acid is treated with warmpotassium permanganate followed by acidification, the only organic products are dodecanoic acid and adipic acid. TheNMR spectrum shows absorptions of vinyl protons split by coupling constants of 7 Hz and 10 Hz. Propose a structure forpetroselenic acid, and show how your structure is consistent with these observations.2
(a) Chromic acid oxidation of 4-tert-butyl-1,2-dimethylbenzene yielded a single compound having the molecular formula C12H14O4. What was this compound?(b) What product is expected from chromic acid oxidation of 2,3-dihydroindene?
Given the chemical equation in the synthesis of benzoic acid from toluene and potassium permanganate:
C7H8(I) + 2KMnO4(aq) → KC7H5O2 + 2MnO2 (s) + KOH (aq) + H2O (I)
KC2H5O2 (aq) + HCl (aq) → C7H8O2 (s) + KCl (aq)
MW: C7H8 = 92.14
KMnO4 = 158.03
MnO2 = 86.94
KC7H5O2 = 160.21
C7H8O2 = 122
Density: C7H8 = 0.87 g/mL
KMnO4 = 2.7 g/mL
KC7H5O2 = 1.5 g/mL
C7H8O2 = 1.27 g/mL
If 1 mL of toluene and 4 mL of 50% w/v potassium permanganate solution are used to synthesize the benzoic acid in a reflux set-up, calculate the theoretical yield of benzoic acid. Show your complete solution and underline your final answer.
Chapter 25 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
Ch. 25.3 - Prob. 25.1PCh. 25.3A - Prob. 25.2PCh. 25.3B - Give an equaton for the complete transestenfcation...Ch. 25.4 - Prob. 25.4PCh. 25.4 - Several commercial laundry soaps contain...Ch. 25.4 - Prob. 25.6PCh. 25.4 - Prob. 25.7PCh. 25.5 - Prob. 25.8PCh. 25.6 - How would you use a simple extraction to separate...Ch. 25.6 - Prob. 25.10P
Ch. 25.8A - Circle the isoprene units in geranial, menthol,...Ch. 25.8B - Prob. 25.12PCh. 25.8B - Prob. 25.13PCh. 25 - Prob. 25.14SPCh. 25 - Prob. 25.15SPCh. 25 - Show how you would convert oleic acid to the...Ch. 25 - Give the general classification of each compound....Ch. 25 - Phospholipids undergo saponification much like...Ch. 25 - Prob. 25.19SPCh. 25 - Prob. 25.20SPCh. 25 - Prob. 25.21SPCh. 25 - Prob. 25.22SPCh. 25 - Prob. 25.23SPCh. 25 - The structure of limonene appears in Problem25-13....Ch. 25 - Prob. 25.25SPCh. 25 - Prob. 25.26SPCh. 25 - Prob. 25.27SPCh. 25 - Prob. 25.28SPCh. 25 - Prob. 25.29SPCh. 25 - Prob. 25.30SPCh. 25 - Prob. 25.31SPCh. 25 - Prob. 25.32SP
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