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
Question
Chapter 19, Problem 25P
Interpretation Introduction
Interpretation:
The starting material required to synthesize the given compounds by acylation of enolate is to be provided.
Concept introduction:
The carbon–carbon bond forming reaction, useful for the synthesis of
In carbonyl condensation reaction, the enolate of one carbonyl compound reacts with the carbonyl group of another.
The Claisen condensation between esters containing α-hydrogens, promoted by a base such as sodium ethoxide, affords β-ketoesters.
The intramolecular version is known as Dieckmann Condensation.
Claisen condensation is a reversible reaction.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
Phenylacetone can form two different enols.(a) Show the structures of these enols.(b) Predict which enol will be present in the larger concentration at equilibrium.(c) Propose mechanisms for the formation of the two enols in acid and in base
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?
Identify A, B, and C, three intermediates in the synthesis of the pain reliever and anesthetic fentanyl.
Chapter 19 Solutions
Organic Chemistry
Ch. 19 - PRACTICE PROBLEM 19.1 (a) Write a mechanism. for...Ch. 19 - Practice Problem 19.2
Since the products obtained...Ch. 19 - Prob. 3PPCh. 19 - PRACTICE PROBLEM 19.4
Write mechanisms that...Ch. 19 - Prob. 5PPCh. 19 - Prob. 6PPCh. 19 - Practice Problem 19.7 The acid-catalyzed aldol...Ch. 19 - Prob. 8PPCh. 19 - Practice Problem 19.9
(a) Provide a mechanism for...Ch. 19 - Prob. 10PP
Ch. 19 - Practice Problem 19.11 Outlined below is a...Ch. 19 - Prob. 12PPCh. 19 - Prob. 13PPCh. 19 - Prob. 14PPCh. 19 - Practice Problem 19.15
Starting with ketones and...Ch. 19 - Practice Problem 19.16 Assuming that dehydration...Ch. 19 - Practice Problem 19.17 What starting compound...Ch. 19 - Practice Problem 19.18
What experimental...Ch. 19 - Prob. 19PPCh. 19 - Practice Problem 19.20
When acrolein (propenal)...Ch. 19 - Prob. 21PPCh. 19 - PRACTICE PROBLEM 19.22
Qutline reasonable...Ch. 19 - Prob. 23PCh. 19 - Show all steps in the following syntheses. You may...Ch. 19 - Prob. 25PCh. 19 - Prob. 26PCh. 19 - Prob. 27PCh. 19 - 19.28 Show how the diketone at the right could be...Ch. 19 - Prob. 29PCh. 19 - 19.30 Write a detailed mechanism for the following...Ch. 19 - Prob. 31PCh. 19 - Prob. 32PCh. 19 - 19.33 Predict the products from each of the...Ch. 19 - Prob. 34PCh. 19 - Show how each of the following transformations...Ch. 19 - Prob. 36PCh. 19 - What reagents would you use to bring about each...Ch. 19 - Prob. 38PCh. 19 - Prob. 39PCh. 19 - 19.40 When the aldol reaction of acetaldehyde is...Ch. 19 - Prob. 41PCh. 19 - Prob. 42PCh. 19 - 19.43 The following reaction illustrates the...Ch. 19 - What is the structure of the cyclic compound that...Ch. 19 - Prob. 45PCh. 19 - Prob. 46PCh. 19 - Prob. 47PCh. 19 - Predict the products from the following reactions....Ch. 19 - Prob. 49PCh. 19 - Prob. 50PCh. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Allowing acetone to react with 2 molar equivalents...Ch. 19 - (+) Fenchone is a terpenoid that can be isolated...Ch. 19 - Prob. 58PCh. 19 - Prob. 59PCh. 19 - 19.60 Develop a synthesis for the following...Ch. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - Prob. 63PCh. 19 - Prob. 1LGP
Knowledge Booster
Similar questions
- Etoposide, sold as a phosphate derivative with the trade name of Etopophos, is used for the treatment of lung cancer, testicular cancer, and lymphomas. (a) Locate the acetals in etoposide. (b) What products are formed when all of the acetals are hydrolyzed with aqueous acid?arrow_forwardShow how you would synthesize octanal from each compound. You may use any necessary reagents.(a) octan-1-olarrow_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
- Show how you would synthesize each compound, starting with an ester containing nomore than eight carbon atoms. Any other necessary reagents may be used.(a) Ph3C¬OH (b) (PhCH2)2CHOHarrow_forwardPredict the major products formed when benzoyl chloride (PhCOCl) reacts with the following reagents.(a) ethanol (b) sodium acetate (c) anilinearrow_forwardA key step in the synthesis of the narcotic analgesic meperidine (trade name Demerol) is the conversion of phenylacetonitrile to X. (a) What is the structure of X? (b) What reactions convert X to meperidine?arrow_forward
- When phenyl 3,4-dimethylbenzoate undergoes electrophilic aromatic substitution, one ring reacts much more readily than the other. (a) Which one is it? Encircle the ring (b) Explain your answer. (c) Draw the resulting product/s when it undergoes bromination reaction. Product (c) (a) Explanation (b)arrow_forwardA key step in the synthesis of the narcotic analgesic meperidine (tradename Demerol) is the conversion of phenylacetonitrile to X. (a) What isthe structure of X? (b) What reactions convert X to meperidine ?arrow_forwardRank the compounds in each of the following groups in order of their reactivity to electrophilic substitution: (a) Nitrobenzene, phenol, toluene, benzene (b) Phenol, benzene, chlorobenzene, benzoic acid (c) Benzene, bromobenzene, benzaldehyde, anilinearrow_forward
- Draw a structural formula for the product formed by treating butanal with each reagent. (a) LiA1H4LiA1H4 followed by H2OH2O (b) NaBH4NaBH4 in CH3OH/H2O (c) H2/Pt (d) Ag(NH3)2+in NH3/H2O (e) H2CrO4, heat (f) HOCH2CH2OH,HClarrow_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_forwardPropylene oxide is a chiral molecule. Hydrolysis of propylene oxide gives propylene glycol, another chiral molecule.(a) Draw the enantiomers of propylene oxide.(b) Propose a mechanism for the acid-catalyzed hydrolysis of pure (R)-propylene oxide.(c) Propose a mechanism for the base-catalyzed hydrolysis of pure (R)-propylene oxide.(d) Explain why the acid-catalyzed hydrolysis of optically active propylene oxide gives a product with lowerenantiomeric excess and a rotation opposite that of the product of the base-catalyzed hydrolysis.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
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning