Organic Chemistry
8th Edition
ISBN: 9781337516402
Author: Brown
Publisher: Cengage
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Chapter 19, Problem 19.60P
Following is a retrosynthetic analysis for an intermediate in the industrial synthesis of vitamin A.
- (a) Addition of one mole of HCl to isoprene gives 4-chloro-2-methyl-2-butene as the major product. Propose a mechanism for this addition and account for its regioselectivity.
- (b) Propose a synthesis of the vitamin A precursor from this allylic chloride and ethyl acetoacetate.
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(c) The following data have been obtained for the hydrolysis of sucrose, C12H22O11, to
glucose, C6H12O6, and fructose C6H12O6, in acidic solution:
C12H22O11 + H2O → C6H12O6 + C6H12O6
[sucrose]/mol dm³
t/min
0
0.316
14
0.300
39
0.274
60
0.256
80
0.238
110
0.211
(i) Graphically prove the order of the reaction and determine the rate constant of the
reaction.
(ii) Determine the half-life, t½ for the hydrolysis of sucrose.
(III) adsorbent
(b) Adsorption of the hexacyanoferrate (III) ion, [Fe(CN)6] ³, on y-Al2O3 from aqueous
solution was examined. The adsorption was modelled using a modified Langmuir
isotherm, yielding the following values of Kat pH = 6.5:
(ii)
T/K
10-10 K
280
2.505
295
1.819
310
1.364
325
1.050
Determine the enthalpy of adsorption, AadsHⓇ.
If the reported value of entropy of adsorption, Aads Se = 146 J K-1 mol-1 under the above
conditions, determine Aads Gº.
with full details solution please
Chapter 19 Solutions
Organic Chemistry
Ch. 19.2 - Prob. 19.1PCh. 19.2 - Prob. 19.2PCh. 19.2 - Prob. 19.3PCh. 19.3 - Prob. 19.4PCh. 19.3 - Prob. 19.5PCh. 19.3 - Prob. 19.6PCh. 19.5 - Prob. 19.7PCh. 19.5 - Prob. 19.8PCh. 19.5 - Prob. 19.9PCh. 19.6 - Prob. 19.10P
Ch. 19.6 - Prob. 19.11PCh. 19.7 - Prob. 19.12PCh. 19.8 - Prob. 19.13PCh. 19.8 - Prob. 19.14PCh. 19.8 - Prob. 19.15PCh. 19.8 - Prob. 19.16PCh. 19.9 - Prob. 19.17PCh. 19.9 - Prob. AQCh. 19.9 - Prob. BQCh. 19.9 - Prob. CQCh. 19.9 - Prob. DQCh. 19.9 - Prob. EQCh. 19.9 - Prob. FQCh. 19.9 - Prob. GQCh. 19.9 - Intermediate G in Synthesis III is produced as a...Ch. 19.9 - Prob. IQCh. 19.9 - Prob. JQCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Cyclohexene can be converted to...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Draw structural formulas for the -ketoesters...Ch. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Propose a synthesis for each ketone, using as one...Ch. 19 - Prob. 19.35PCh. 19 - Claisen condensation between diethyl phthalate and...Ch. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Enamines normally react with methyl iodide to give...Ch. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Show experimental conditions by which to carry out...Ch. 19 - Prob. 19.55PCh. 19 - The compound 3,5,5-trimethyl-2-cyclohexenone can...Ch. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - The widely used anticoagulant warfarin (see...Ch. 19 - Following is a retrosynthetic analysis for an...Ch. 19 - Following are the steps in one of the several...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - In Problem 7.28, we saw this two-step sequence in...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - The following molecule undergoes an intramolecular...
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