Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 22.SE, Problem 63AP
As far back as the 16th century, South American Incas chewed the leaves of the coca bush, Erythroxylon coca, to combat fatigue. Chemical studies of Erythroxylon coca by Friedrich Wöhler in 1862 resulted in the discovery of cocaine, C17H21NO4, as the active component. Basic hydrolysis of cocaine leads to methanol, benzoic acid, and another compound called ecgonine, C9H15NO3. Oxidation of ecgonine with CrO3 yields a keto acid that readily loses CO2 on heating, giving tropinone.
(a) What is a likely structure for the keto acid?
(b) What is a likely structure for ecgonine, neglecting stereochemistry?
(c) What is a likely structure for cocaine, neglecting stereochemistry?
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Don't used Ai solution
What is the absorption spectrum of a solution of naphthalene in benzene , and the vibronic transitions responsible for the vibrational fine structure ?
3. Titanium(III) chloride can be used to catalyze the polymerization of ethylene. It is prepared by hydrogen reduction of
Titanium(IV) chloride. Reaction of hydrogen gas with titanium(IV) chloride gas produces solid titanium(III) chloride and
hydrogen chloride gas.
(a) Write a BALANCED chemical reaction for the preparation of titanium(III) chloride
(b) A 250 L reaction vessel at 325°C is filled with hydrogen gas to a pressure of 1.3 atm. Titanium(IV) chloride is then added
to bring the total pressure to 3.00 atm. How many grams of titanium(III) chloride will be produced after completion of the
reaction?
(c) What will be the pressure of the resulting hydrogen chloride gas that is also produced?
Chapter 22 Solutions
Organic Chemistry
Ch. 22.1 - Prob. 1PCh. 22.1 - How many acidic hydrogens does each of the...Ch. 22.1 - Prob. 3PCh. 22.3 - Write the complete mechanism for the deuteration...Ch. 22.3 - Prob. 5PCh. 22.4 - If methanol rather than water is added at the end...Ch. 22.5 - Prob. 7PCh. 22.5 - Draw a resonance structure of the acetonitrile...Ch. 22.6 - If methanol rather than water is added at the end...Ch. 22.7 - Prob. 10P
Ch. 22.7 - Draw a resonance structure of the acetonitrile...Ch. 22.7 - Why do you suppose ketone halogenations in acidic...Ch. 22.7 - Prob. 13PCh. 22.7 - Prob. 14PCh. 22.7 - Prob. 15PCh. 22.7 - Prob. 16PCh. 22.SE - Prob. 17VCCh. 22.SE - Prob. 18VCCh. 22.SE - Prob. 19VCCh. 22.SE - Prob. 20MPCh. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Predict the product(s) and provide the mechanism...Ch. 22.SE - Prob. 23MPCh. 22.SE - In the Hell–Volhard–Zelinskii reaction, only a...Ch. 22.SE - Prob. 25MPCh. 22.SE - Nonconjugated , -unsaturated ketones, such as...Ch. 22.SE - Prob. 27MPCh. 22.SE - Using curved arrows, propose a mechanism for the...Ch. 22.SE - Prob. 29MPCh. 22.SE - One of the later steps in glucose biosynthesis is...Ch. 22.SE - The Favorskii reaction involves treatment of an...Ch. 22.SE - Treatment of a cyclic ketone with diazomethane is...Ch. 22.SE - Prob. 33MPCh. 22.SE - Amino acids can be prepared by reaction of alkyl...Ch. 22.SE - Amino acids can also be prepared by a two-step...Ch. 22.SE - Heating carvone with aqueous sulfuric acid...Ch. 22.SE - Identify all the acidic hydrogens (pKa 25) in the...Ch. 22.SE - Rank the following compounds in order of...Ch. 22.SE - Prob. 39APCh. 22.SE - Base treatment of the following , -unsaturated...Ch. 22.SE - Prob. 41APCh. 22.SE - Prob. 42APCh. 22.SE - Prob. 43APCh. 22.SE - Which, if any, of the following compounds can be...Ch. 22.SE - Prob. 45APCh. 22.SE - Prob. 46APCh. 22.SE - Prob. 47APCh. 22.SE - How might you convert geraniol into either ethyl...Ch. 22.SE - Prob. 49APCh. 22.SE - One way to determine the number of acidic...Ch. 22.SE - Prob. 51APCh. 22.SE - Prob. 52APCh. 22.SE - Prob. 53APCh. 22.SE - Prob. 54APCh. 22.SE - Prob. 55APCh. 22.SE - Prob. 56APCh. 22.SE - All attempts to isolate primary and secondary...Ch. 22.SE - How would you synthesize the following compounds...Ch. 22.SE - Prob. 59APCh. 22.SE - Prob. 60APCh. 22.SE - Prob. 61APCh. 22.SE - Prob. 62APCh. 22.SE - As far back as the 16th century, South American...Ch. 22.SE - The key step in a reported laboratory synthesis of...Ch. 22.SE - Prob. 65AP
Knowledge Booster
Learn more about
Need a deep-dive on the concept behind this application? Look no further. Learn more about this topic, chemistry and related others by exploring similar questions and additional content below.Similar questions
- 1. Sodium azide (NaN3) is the primary chemical substance used in automobile air bags. Upon impact, the decomposition of sodium azide is initiated to produce sodium metal and nitrogen gas which then inflates the bag. How many liters of nitrogen gas are produced at 1.15 atm and 30.0°C when 145.0 grams of sodium azide decomposes? 2. Calcium carbonate (such as that in limestone) reacts with aqueous hydrochloric acid to produce carbon dioxide, aqueous calcium chloride and water. How many liters of carbon dioxide are produced at 20°C and 745 torr when 3.583 grams of calcium carbonate is dissolved in solution containing 1.550 grams of hydrochloric acid?arrow_forwardShow all work (where appropriate) for full credit. 1. Describe (steps, equipment and quantities) how to accurately prepare 250.0 mL of a 0.0075 M solution of NaCl (aq) from a 500 mL, 0.0500 M stock solution. 2. Describe (steps, equipment and quantities) how to accurately prepare 250.0 mL of a 0.0075 M solution of NaCl (aq) from 100 g of solid NaCl.arrow_forward5. An unlabeled gas cylinder was recently found in the laboratory. A sample of the gas was removed and analyzed. A 500.0 mL sample of the gas at 15°C and a pressure of 736 mmHg was found to weigh 2.688 g. Determine the molar mass of the gas. What element is the gas?arrow_forward
- 4. Nitrogen gas is commonly sold in 49.0 L steal cylinders at a pressure of 150 atm. (a) How many moles of nitrogen are in the container if the temperature of the cylinder is 21°C. (b) How many moles of nitrogen will there be if the container above is heated to 100°C? (careful here) (c) What is the mass of nitrogen gas in the cylinder in part (a)? (d) What volume would the nitrogen occupy at 21°C, if the pressure was reduced to 1.02 atm? (e) What would be the pressure of the nitrogen gas in the cylinder when the temperature is raised to 39°C?arrow_forward6. A 0.4550 g sample of an unknown organic compound with the empirical formula CH2O was placed into a 150.0 ml vessel and was vaporized into a gas. At 175.0°C, the pressure of the vaporized compound was measured at 941.1 torr. (a) Determine the molar mass of the compound (b) Determine the molecular formula of the compound.arrow_forwardDon't used Ai solutionarrow_forward
- 3. A particular reaction calls for 2.40 g of chloride ion. The only source of chloride ion available is a 0.00300 M stock solution of strontium chloride. How much (in L) of this solution is needed for this reaction?arrow_forwardAbsorption Spectrum of NaphthaleneTitle: Understanding the Absorption Spectrum of NaphthaleneGraph: Show a graph with labeled peaks indicating the absorption spectrum of naphthalene in a suitable solventarrow_forwardDon't used Ai solutionarrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Characteristic Reactions of Benzene and Phenols; Author: Linda Hanson;https://www.youtube.com/watch?v=tjEqEjDd87E;License: Standard YouTube License, CC-BY
An Overview of Aldehydes and Ketones: Crash Course Organic Chemistry #27; Author: Crash Course;https://www.youtube.com/watch?v=-fBPX-4kFlw;License: Standard Youtube License