ORGANIC CHEMISTRY (LOOSELEAF)
6th Edition
ISBN: 9781260475630
Author: SMITH
Publisher: MCG
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Chapter 22.6, Problem 21P
Two steps in a synthesis of the analgesic ibuprofen, the chapter-opening molecule, include a carbonyl condensation reaction, followed by an alkylation reaction. Identify intermediates A and B in the synthesis of ibuprofen.
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Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l). The chemist discovers a more efficient catalyst that can produce ethyl butyrate with a 78.0% yield. How many grams would be produced from 8.50 gof butanoic acid and excess ethanol? Express your answer in grams to three significant figures.
Ethyl butyrate, CH3CH2CH2CO2CH2CH3, is an artificial fruit flavor commonly used in the food industry for such flavors as orange and pineapple. Its fragrance and taste are often associated with fresh orange juice, and thus it is most commonly used as orange flavoring.It can be produced by the reaction of butanoic acid with ethanol in the presence of an acid catalyst (H+): CH3CH2CH2CO2H(l)+CH2CH3OH(l)H+⟶CH3CH2CH2CO2CH2CH3(l)+H2O(l)
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Chapter 22 Solutions
ORGANIC CHEMISTRY (LOOSELEAF)
Ch. 22.1 - Prob. 1PCh. 22.1 - Prob. 2PCh. 22.1 - Problem 24.3
What unsaturated carbonyl compound is...Ch. 22.1 - Prob. 4PCh. 22.1 - Prob. 5PCh. 22.2 - Prob. 6PCh. 22.2 - Problem 24.7
Draw the products formed in each...Ch. 22.4 - Prob. 15PCh. 22.4 - Prob. 16PCh. 22.5 - Problem 24.16
What ester is formed when each...
Ch. 22.6 - Prob. 18PCh. 22.6 - Prob. 19PCh. 22.6 -
Draw the products of each reaction.
a. b.
Ch. 22.6 - Problem 24.20
Two steps in a synthesis of the...Ch. 22.7 - Prob. 22PCh. 22.8 - Problem 24.22
Which of the following compounds can...Ch. 22.8 - Prob. 24PCh. 22.8 - Problem 24.24
What starting materials are needed...Ch. 22 - Prob. 29PCh. 22 - 24.29 What steps are needed to convert A to B?
Ch. 22 - Prob. 31PCh. 22 - 24.31 Draw the product formed in each directed...Ch. 22 - Prob. 33PCh. 22 - 24.33 What starting materials are needed to...Ch. 22 - Prob. 35PCh. 22 - Prob. 36PCh. 22 - 24.36 Identify the structures of C and D in the...Ch. 22 - Prob. 38PCh. 22 - Prob. 39PCh. 22 - 24.39 Draw the product formed from a Claisen...Ch. 22 - Prob. 41PCh. 22 - 24.41 Even though B contains three ester groups, a...Ch. 22 - Prob. 43PCh. 22 - Prob. 44PCh. 22 - 24.44 Vetivone is isolated from vetiver, a...Ch. 22 - Draw the product of each Robinson annulation from...Ch. 22 - Prob. 50PCh. 22 - Prob. 51PCh. 22 - 24.52 Draw a stepwise mechanism for the following...Ch. 22 - Prob. 53PCh. 22 - Prob. 54PCh. 22 - Prob. 55PCh. 22 - Prob. 56PCh. 22 - Prob. 57PCh. 22 - Prob. 58PCh. 22 - Prob. 59PCh. 22 - 24.62 Devise a synthesis of each compound from ,...Ch. 22 - Prob. 63P
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- Nonconjugated , -unsaturated ketones, such as 3-cyclohexenone, are in an acid-catalyzed equilibrium with their conjugated , -unsaturated isomers. Propose a mechanism for this isomerization.arrow_forwardClaisen condensation between diethyl phthalate and ethyl acetate followed by saponification, acidification, and decarboxylation forms a diketone, C9H6O2. Propose structural formulas for compounds A and B and the diketone.arrow_forwardProstaglandins are a class of eicosanoids, fatty acid derivatives involved in a variety of important phenomena, including fever, inflammation, and pain. The first step in prostaglandin synthesis involves the conversion of the 20-carbon fatty acid arachidonic acid to PGG2 by the enzyme prostaglandin endoperoxide synthase, or cyclooxy: Ibuprofen is one of several inhibitors of cyclooxogenase used therapeutically. Arachidonic acid 20₂ 0.5 1.0 1.5 2.5 3.5 cyclooxrygenase PGG₂ JOH محمد The following kinetic data were obtained for the enzyme cyclooxygenase in the absence of any inhibitor (1), and in the presence of ibuprofen (2) at a concentration of 48 [arachidonic acid] (uM) (1) v(uM/min) (2) v(uM/min) 23.5 32.2 36.9 41.8 44.0 16.67 25.25 30.49 37.04 38.91 Ibuprofen A. Plot the data in standard Michaelis-Menten form as well as in double-reciprocal form. B. Determine Vmax and Km for the enzyme. C. Based on this limited data set, what type of inhibition does ibuprofen likely exhibit?…arrow_forward
- Digitalis is a preparation made from the dried seeds and leaves of the purple foxglove, Digitalis purpurea, a plant native to southern and central Europe and cultivated in the United States. The preparation is a mixture of several active components, including digitalin. Digi- talis is used in medicine to increase the force of myocardial contraction and as a conduction depressant to decrease heart rate (the heart pumps more forcefully but less often). HC OH H,C H CH3 H. H. (a) Describe this glycosidic bond OCH, H A (b) Draw an open-chain Fischer projection of this monosaccharide CH3 H. (e) Describe this glycosidic bond OCH, HA H. HO H) H. OH НО (d) Name this monosaccharide unit H. OH Digitalinarrow_forwardDraw a stepwise mechanism for the formation of A from an alcohol and acid chloride. A was converted in one step to blattellaquinone, the sex pheromone of the female German cockroach, Blattella germanica.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forward
- 15.) Which of the following esters, upon hydrolysis, produces a diol as one of the products? A) hydroxymethyl hexanoate D) cyclohexyl hexanoate B) 2-methylpropyl butanoate E) diethyl decanedioate C) ethyl 3-iodopentanoate F) cyclopropyl benzoatearrow_forwardAcetal derivatives of aldehydes and ketones are prepared by an acid-catalyzed dehydration reaction with alcohols or diols. Using more pictures than words, draw a reaction and a mechanism that shows the formation of acetal.arrow_forwardOrganic Synthesis is created when Acetophenone is reacted with pyridinium tribromide. Determine the product formed.arrow_forward
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