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 2PP
Practice Problem 18.2
Would optically active ketones such as the following undergo acid-or base-catalyzed racemization? Explain your answer.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
Quinapril (trade name Accupril) is used to treat high blood pressure and congestive heart failure. One step in the synthesis of quinapril involves reaction of the racemic alkyl bromide A with a single enantiomer of the amino ester B. (a) What two products are formed in this reaction? (b) Given the structure of quinapril, which one of these two products is needed to synthesize the drug?
Practice Problem 19.54
Z Your answer is partially correct. Try again.
Predict the major product(s) (A - K) from the treatment of acetone with the following compounds (a-c):
NH2
HO
Eto
OEt
A:
B:
C:
D:
E:
F:
OH
OH
но
CN
G:
H:
I:
J:
(a) [H*], excess EtOH, (-H20)
Major Product(s):
(ь) NaBH4, Meон
B
Major Product(s):
(c) LAH followed by H20
Major Product(s):
SHOW HINT
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
Q4. Which property of rubbing alcohol is a chemical property?
a) Density (0.786 g/cm3)
b) Flammability
c) Bo...
Chemistry: A Molecular Approach (4th Edition)
33. Consider the reaction:
The tabulated data were collected for the concentration of C4H8 as a function...
Chemistry: Structure and Properties
1. What did each of the following scientists contribute to our knowledge of the atom?
a. William Crookes
b. E...
Chemistry For Changing Times (14th Edition)
Given that is a stronger acid than what is the chemical reaction if solutions containing these ions are mixe...
Chemistry: The Molecular Nature of Matter
One of the following statements is true and the other as false regarding the first-order reaction 2AB+C . Ident...
General Chemistry: Principles and Modern Applications (11th 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
- (a) Draw two different halo ketones that can form A by an intramolecular alkylation reaction. (b) How can A be synthesized by an acetoacetic ester synthesis?arrow_forward24.82 When the compound shown here is heated, ethene gas is evolved and a product with the formula C14H3O2 is formed. The 'H NMR and 13C NMR spectra of C14H8O2 are shown below. (There are two signals >150 ppm in the 13C NMR spectrum. Recall that the 13C NMR signal at 77 ppm is from the CDCI3 solvent.) (a) Draw the structure of C,14H3O2. (b) Draw the mechanism that accounts for its formation. (c) What is the main driving force that favors the products of this reaction? ? C14H3O2 C14H8O2 9. 8 7 6 4 3 2 1 250 200 150 100 50 Chemical shift (ppm) Chemical shift (ppm)arrow_forward(a) Draw two different halo ketones that can form A by an intramolecularalkylation reaction. (b) How can A be synthesized by an acetoacetic estersynthesis?arrow_forward
- please help with this question. thank you. The following sequence, beginning with a cyclic hemiacetal (compound A), was part of a recently reported enantiospecific synthesis of a powerful sex pheromone (currently used in pest management) of the mealybug Pseudococcus viburni: Draw the structures of compound B and C. Provide a plausible mechanism to explain the transformation from compound C into compound D. Identify the reagents you would need to convert compound D into compound F (in just two steps). Also identify the structure of compound E.arrow_forwardShow how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acidarrow_forwardEach of the following can be prepared by an intramolecular aldol condensation of a diketone. Apply retrosynthetic analysis to deduce the structure of the diketone in each case.arrow_forward
- (a) p-Nitrobenzaldehyde is reactive toward nucleophilic additions than p- more methoxybenzaldehyde. Draw both of the molecular structures and explain the observation. (b) Cyclohexanone forms a cyanohydrin in good yield but 2,2,6-trimethylcyclohexanone does not. Draw both of the molecular structures and explain the observation.arrow_forwardGive detailed answer with explanation please don't give Handwritten answerarrow_forwardAttenol A and pinnatoxin A are natural products isolated from marine sources. (a) Locate the acetals, hemiacetals, imines, and enamines in both compounds. (b) Draw the hydrolysis product formed when attenol A is treated with aqueous acid. Include stereochemistry at all stereogenic centers.arrow_forward
- (a) Explain the mechanism of a nucleophilic attack on the carbonyl group of an aldehyde or a ketone.(b) An organic compound (A) (molecular formula CgH16Q2) was hydrolysed with dilute sulphuric acid to give a carboxylic acid (B) and an alcohol (C). Oxidation of (C) with chromic acid also produced (B). On dehydration (C) gives but-1-ene. Write the equations for the reactions involved.arrow_forwardBoth pyridine and pyrrole are nitrogen containing aromatic heterocyclic compounds. When treated with HCl, only pyridine forms the hydrochloride salt, where as pyrrole is unreactive. What is the best explanation for this observed reactivity.arrow_forward• PRACTICE PROBLEM 18.14 Show how you could employ enamines in syntheses of the following compounds: Een önös (c) (a) (b) (d) OEtarrow_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