Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
expand_more
expand_more
format_list_bulleted
Concept explainers
Videos
Textbook Question
Chapter 18, Problem 2LGP
Dehydroabietic acid is a natural product isolated from Pinus palustris. It is structurally related to abietic acid, which comes from rosin. The synthesis of dehydroabietic acid (J. Am. Chem. Soc. 1962, 84, 284–292) was accomplished by Gilbert Stork. In the course of this synthesis, Stork discovered his famous enamine reaction.
(a) Write detailed mechanisms for the reactions from 6 to 8 below.
(b) Write detailed mechanisms for all of the reactions from 9 to 11 in Stork’s synthesis of dehydroabietic acid. Note that 11 contains a dithioacetal, which forms similarly to acetals you have already studied (Chapter 16).
(Fleming, I., Selected
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solution
Students have asked these similar questions
Calculating standard reaction free energy from standard reduction...
Using standard reduction potentials from the ALEKS Data tab, calculate the standard reaction free energy AG° for the following redox reaction.
Be sure your answer has the correct number of significant digits.
3+
H2(g)+2OH¯ (aq) + 2Fe³+ (aq) → 2H₂O (1)+2Fe²+ (aq)
0
kJ
x10
Х
?
olo
18
Ar
Calculating the pH of a weak base titrated with a strong acid
An analytical chemist is titrating 184.2 mL of a 0.7800M solution of dimethylamine ((CH3)
NH with a 0.3000M solution of HClO4. The pK₁ of
dimethylamine is 3.27. Calculate the pH of the base solution after the chemist has added 424.1 mL of the HClO solution to it.
2
4
Note for advanced students: you may assume the final volume equals the initial volume of the solution plus the volume of HClO 4 solution added.
Round your answer to 2 decimal places.
pH = ☐
☑
?
000
18
Ar
1
B
Using the Nernst equation to calculate nonstandard cell voltage
A galvanic cell at a temperature of 25.0 °C is powered by the following redox reaction:
MnO2 (s)+4H* (aq)+2Cr²+ (aq) → Mn²+ (aq)+2H₂O (1)+2Cr³+ (aq)
+
2+
2+
3+
Suppose the cell is prepared with 7.44 M H* and 0.485 M Cr²+ in one half-cell and 7.92 M Mn² and 3.73 M Cr³+ in the other.
Calculate the cell voltage under these conditions. Round your answer to 3 significant digits.
☐
x10
μ
Х
5
?
000
日。
Chapter 18 Solutions
Organic Chemistry
Ch. 18 - Prob. 1PPCh. 18 - Practice Problem 18.2 Would optically active...Ch. 18 - Prob. 3PPCh. 18 - Practice Problem 18.4 Why do we say that the...Ch. 18 - Prob. 5PPCh. 18 - Practice Problem 18.6 (a) Write a reaction...Ch. 18 - PRACTICE PROBLEM 18.7
Show how you would use the...Ch. 18 - Practice Problem 18.8 The acetoacetic ester...Ch. 18 - Practice Problem 18.9
In the synthesis of the keto...Ch. 18 - PRACTICE PROBLEM 18.10 How would you use the...
Ch. 18 - PRACTICE PROBLEM 18.11
How would you use the...Ch. 18 - PRACTICE PROBLEM 18.12 Outline all steps in a...Ch. 18 - PRACTICE PROBLEM 18.13
The antiepileptic drug...Ch. 18 - PRACTICE PROBLEM 18.14 Show how you could employ...Ch. 18 - Prob. 15PCh. 18 - Treating a solution of cis-1-decalone with base...Ch. 18 - Prob. 17PCh. 18 - Prob. 18PCh. 18 - Prob. 19PCh. 18 - Prob. 20PCh. 18 - Prob. 21PCh. 18 - Prob. 22PCh. 18 - Prob. 23PCh. 18 - The synthesis of cyclobutanecarboxylic acid given...Ch. 18 - Prob. 25PCh. 18 - Prob. 26PCh. 18 - Prob. 27PCh. 18 - Prob. 28PCh. 18 - Compound J, a compound with two four-membered...Ch. 18 - Prob. 30PCh. 18 - Prob. 31PCh. 18 - 18.32 Shown below is a synthesis of the elm bark...Ch. 18 - 18.33 (a) A compound U gives a negative iodoform...Ch. 18 - 18.34 Compound A has the molecular formula and...Ch. 18 - Prob. 35PCh. 18 - Prob. 36PCh. 18 - Prob. 37PCh. 18 - Prob. 38PCh. 18 - 1. -Carotene is a highly conjugated hydrocarbon...Ch. 18 - Dehydroabietic acid is a natural product isolated...
Additional Science Textbook Solutions
Find more solutions based on key concepts
How do food chains and food webs differ? Which is the more accurate representation of feeding relationships in ...
Biology: Life on Earth (11th Edition)
64. Determine the [H3O+] and pH of a 0.200 M solution of formic acid.
Chemistry: A Molecular Approach (4th Edition)
Modified True/False 9. A giant bacterium that is large enough to be seen without a microscope is Selenomonas.
Microbiology with Diseases by Body System (5th Edition)
41. Humans vary in many ways from one another. Among many minor phenotypic differences are the following five i...
Genetic Analysis: An Integrated Approach (3rd Edition)
4. The lipid portion of a typical bilayers is about 30 A0 thick.
a. Calculate the minimum number of residues in...
Biochemistry: Concepts and Connections (2nd Edition)
2.81 In which of the fo1losing pairs do both numbers contain the same number of significant figures? (2.2)
a....
Chemistry: An Introduction to General, Organic, and Biological Chemistry (13th Edition)
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
- Calculating standard reaction free energy from standard reduction... Using standard reduction potentials from the ALEKS Data tab, calculate the standard reaction free energy AG° for the following redox reaction. Be sure your answer has the correct number of significant digits. NO (g) +H₂O (1) + Cu²+ (aq) → HNO₂ (aq) +H* (aq)+Cu* (aq) kJ - ☐ x10 x10 olo 18 Ararrow_forwardCalculating the pH of a weak base titrated with a strong acid b An analytical chemist is titrating 116.9 mL of a 0.7700M solution of aniline (C6H5NH2) with a 0.5300M solution of HNO3. The pK of aniline is 9.37. Calculate the pH of the base solution after the chemist has added 184.2 mL of the HNO 3 solution to it. Note for advanced students: you may assume the final volume equals the initial volume of the solution plus the volume of HNO3 solution added. Round your answer to 2 decimal places. pH = ☐ ☑ 5arrow_forwardQUESTION: Find the standard deviation for the 4 different groups 5.298 3.977 223.4 148.7 5.38 4.24 353.7 278.2 5.033 4.044 334.6 268.7 4.706 3.621 305.6 234.4 4.816 3.728 340.0 262.7 4.828 4.496 304.3 283.2 4.993 3.865 244.7 143.6 STDEV = STDEV = STDEV = STDEV =arrow_forward
- QUESTION: Fill in the answers in the empty green boxes regarding 'Question 5: Calculating standard error of regression' *The images of the data showing 'coefficients for the standard curve' have been providedarrow_forwardUsing the Nernst equation to calculate nonstandard cell voltage Try Again Your answer is wrong. In addition to checking your math, check that you used the right data and DID NOT round any intermediate calculations. A galvanic cell at a temperature of 25.0 °C is powered by the following redox reaction: 2+ 2+ Sn²+ Ba(s) (aq) + Ba (s) Sn (s) + Ba²+ (aq) →>> Suppose the cell is prepared with 6.10 M Sn 2+ 2+ in one half-cell and 6.62 M Ba in the other. Calculate the cell voltage under these conditions. Round your answer to 3 significant digits. 1.71 V ☐ x10 ☑ 5 0/5 ? 00. 18 Ararrow_forwardQuestion: Find both the b (gradient) and a (y-intercept) value from the list of data below: (x1 -x̄) 370.5 (y1 - ȳ) 5.240 (x2 - x̄) 142.5 (y2 - ȳ) 2.004 (x3 - x̄) 28.5 (y3 - ȳ) 0.390 (x4 - x̄) -85.5 (y4 - ȳ) -1.231 (x5 - x̄) -199.5 (y5 - ȳ) -2.829 (x6 - x̄) -256.5 (y6 - ȳ) -3.575arrow_forward
- Calculating standard reaction free energy from standard reduction... Using standard reduction potentials from the ALEKS Data tab, calculate the standard reaction free energy AG° for the following redox reaction. Be sure your answer has the correct number of significant digits. 3Cu+ (aq) + Cro²¯ (aq) +4H₂O (1) → 3Cu²+ (aq) +Cr(OH)3 (s)+5OH˜¯ (aq) 0 kJ ☐ x10 00. 18 Ararrow_forwardCalculating the pH of a weak base titrated with a strong acid An analytical chemist is titrating 241.7 mL of a 0.4900M solution of methylamine (CH3NH2) with a 0.7800M solution of HNO3. The pK of methylamine is 3.36. Calculate the pH of the base solution after the chemist has added 17.7 mL of the HNO3 solution to it. Note for advanced students: you may assume the final volume equals the initial volume of the solution plus the volume of HNO3 solution added. Round your answer to 2 decimal places. pH = ☑ ? 18 Ararrow_forwardThe following is two groups (Regular tomato sauce & Salt Reduced Tomato Sauce) of data recorded by a team analysising salt content in tomato sauce using the MOHR titration method: Regular Tomato Sauce Salt Reduced Tomato Sauce 223.4 148.7 353.7 278.2 334.6 268.7 305.6 234.4 340.0 262.7 304.3 283.2 244.7 143.6 QUESTION: For both groups of data calculate the answers attached in the image.arrow_forward
- The following is a two groups (Regular tomato sauce & Salt Reduced Tomato Sauce) of data recorded by a team analysising salt content in tomato sauce using the MOHR titration method: Regular Tomato Sauce Salt Reduced Tomato Sauce 340.0mmol/L 262.7mmol/L QUESTION: For both groups (Regular & Salt Reduced tomato sauce) of data provide answers to the following calculations below: 1. Standard Deviation (Sx) 2. T Values (t0.05,4) 3. 95% Confidence Interval (mmol/L) 4. [Na+] (mg/100 mL) 5. 95% Confidence Interval (mg/100 mL)arrow_forwardIf we have leucine (2-amino-4-methylpentanoic acid), alanine (2-aminopropanoic acid) and phenylalanine (2-amino-3-phenylpropanoic acid), indicate the tripeptides that can be formed (use the abbreviated symbols Leu., Ala and Phe).arrow_forwardBriefly state why trifluoroacetic acid is more acidic than acetic acid.arrow_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: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Cengage Learning
NMR Spectroscopy; Author: Professor Dave Explains;https://www.youtube.com/watch?v=SBir5wUS3Bo;License: Standard YouTube License, CC-BY