ORGANIC CHEMISTRY W/OWL
9th Edition
ISBN: 9781305717527
Author: McMurry
Publisher: CENGAGE C
expand_more
expand_more
format_list_bulleted
Concept explainers
Question
Chapter 27.SE, Problem 25AP
Interpretation Introduction
Interpretation:
The structure of stearolic acid (C18H32O2) which on catalytic hydrogenation yields stearic acid and upon treatment with ozone gives nonanoic acid and nonanedioic acid is to be proposed.
Concept introduction:
Catalytic hydrogenation reduces double bond and triple bonds in unsaturated compounds to yield saturated compounds. During ozonolysis double bonds are cleaved to yield carbonyl compounds while triple bonds are cleaved to yield carboxylic acids.
To propose:
The structure of stearolic acid (C18H32O2) which on catalytic hydrogenation yields stearic acid and upon treatment with ozone gives nonanoic acid and nonanedioic acid.
Expert Solution & Answer

Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Consider this organic reaction:
OH
Draw the major products of the reaction in the drawing area below. If there won't be any major products, because this reaction won't happen at a significant
rate, check the box under the drawing area instead.
Click and drag to start drawing a structure.
x
0:
の
C
Explain the reasons for a compound's greater or lesser reactivity toward electrophilic aromatic substitution. Give reasons.
Draw the products of a reaction of the following alkyle chloride, shown below in the 3D ball and stick model with NaSCH3. Ignore inorganic byproducts. In the figure, a gray ball indicates a carbon atom a white ball indicates a hydrogen atom anda agreen ball indicated a chlorine atom
Chapter 27 Solutions
ORGANIC CHEMISTRY W/OWL
Ch. 27.1 - Carnauba wax, used in floor and furniture...Ch. 27.1 - Draw structures of glyceryl tripalmitate and...Ch. 27.2 - Prob. 3PCh. 27.2 - Write the saponication reaction of glyceryl...Ch. 27.4 - Prob. 5PCh. 27.5 - Prob. 6PCh. 27.5 - Prob. 7PCh. 27.6 - Draw the following molecules in chair...Ch. 27.6 - Lithocholic acid is an A–B cis steroid found in...Ch. 27.7 - Prob. 10P
Ch. 27.SE - Prob. 11VCCh. 27.SE - Propose a biosynthetic pathway for the...Ch. 27.SE - Identify the following fatty acid, and tell...Ch. 27.SE - Prob. 14MPCh. 27.SE - Prob. 15MPCh. 27.SE - Prob. 16MPCh. 27.SE - Prob. 17APCh. 27.SE - Fats can be either optically active or optically...Ch. 27.SE - Prob. 19APCh. 27.SE - Show the products you would expect to obtain from...Ch. 27.SE - Draw a Newman projection along the C2-C3 bond of...Ch. 27.SE - The plasmalogens are a group of lipids found in...Ch. 27.SE - Prob. 23APCh. 27.SE - Prob. 24APCh. 27.SE - Prob. 25APCh. 27.SE - Prob. 26APCh. 27.SE - Prob. 27APCh. 27.SE - Prob. 28APCh. 27.SE - Prob. 29APCh. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Assume that acetyl CoA containing a 14C isotopic...Ch. 27.SE - Prob. 34APCh. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Draw the most stable chair conformation of...Ch. 27.SE - Prob. 37APCh. 27.SE - Prob. 38APCh. 27.SE - Prob. 39APCh. 27.SE - What product would you obtain by reduction of...Ch. 27.SE - Prob. 41APCh. 27.SE - Eleostearic acid, C18H30O2, is a rare fatty acid...Ch. 27.SE - Prob. 43APCh. 27.SE - Prob. 44APCh. 27.SE - Propose a synthesis of diethylstilbestrol (Problem...Ch. 27.SE - Prob. 46APCh. 27.SE - Cembrene, C20H32, is a diterpenoid hydrocarbon...Ch. 27.SE - α-Fenchone is a pleasant-smelling terpenoid...Ch. 27.SE - Prob. 49APCh. 27.SE - Propose a mechanism for the biosynthesis of the...
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
- Draw the most stable cations formed in the mass spectrometer by a deavage of the following compound Draw the most stable cations formed in the mass spectrometer by a cleavage of the following compound онarrow_forwardCurved arrows are used to illustrate the flow of electrons. Using the provided starting anand product sytucutrs, draw the curved electron-pusing arrows for the following reaction or mechanistic steps. Be sure to account for all bond-breaking and bind-making stepsarrow_forwardDraw the major elimination and substitution products formed in this reavtion. Use a dash or wedge bond to indicatr the stereochemistry of substituents on assymetric centers, wheere applicable. Ignore any inorganic byproducts.arrow_forward
- Draw the two possible products produced in this E2 elimination. Ignore any inorganic byproductsarrow_forwardDraw the major products of this SN1 reaction. Ignore any inorganic byproducts.arrow_forwardDraw the major elimination and substitution products formed in this reaction. Use a dash or wedge bond to indicate the stereochemistry of substituents on asymmetric centers, wehre applicable. Ignore and inorganic byproducts.arrow_forward
- Curved arrows are used to illustrate the flow of electrons. Using the provided starting and product structures, draw the curved electron-pushing arrows for the following reaction or mechanistic step(s). Be sure to account for all bond-breaking and bond-making steps. Drawing Arrows THE Problem 33 of 35 N. C:0 Na + Submit Drag To Pan +arrow_forwardDraw the product of the E2 reaction shown below. Include the correct stereochemistry. Ignore and inorganic byproducts.arrow_forwardDraw the major producrs of this SN1 reaction. Ignore any inorganic byproducts. Use a dash or wedge bond to indicate the sereochemistry of substituents on asymmetric centers where appllicable.arrow_forward
- 5) Oxaloacetic Acid is an important intermediate in the biosynthesis of citric acid. Synthesize oxaloacetic acid using a mixed Claisen Condensation reaction with two different esters and a sodium ethoxide base. Give your answer as a scheme Hint 1: Your final acid product is producing using a decarboxylation reaction. Hint 2: Look up the structure of oxalic acid. HO all OH oxaloacetic acidarrow_forward20. The Brusselator. This hypothetical system was first proposed by a group work- ing in Brussels [see Prigogine and Lefever (1968)] in connection with spatially nonuniform chemical patterns. Because certain steps involve trimolecular reac tions, it is not a model of any real chemical system but rather a prototype that has been studied extensively. The reaction steps are A-X. B+X-Y+D. 2X+ Y-3X, X-E. 305 It is assumed that concentrations of A, B, D, and E are kept artificially con stant so that only X and Y vary with time. (a) Show that if all rate constants are chosen appropriately, the equations de scribing a Brusselator are: dt A-(B+ 1)x + x²y, dy =Bx-x²y. diarrow_forwardProblem 3. Provide a mechanism for the following transformation: H₂SO A Me. Me Me Me Mearrow_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 LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning

Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning

Chemistry for Today: General, Organic, and Bioche...
Chemistry
ISBN:9781305960060
Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen
Publisher:Cengage Learning
