![OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition](https://www.bartleby.com/isbn_cover_images/9781305582439/9781305582439_smallCoverImage.jpg)
(a)
Interpretation:
The product of the claisen condensation of ethyl phenylacetate in the presence of sodium ethoxide ion has to be shown.
Concept introduction:
When two molecules of an ester undergo condensation, then it is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.
A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.
The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.
(b)
Interpretation:
The product of the claisen condensation of methyl hexanoate in the preesnce of sodium ethoxide ion has to be shown.
Concept introduction:
When two molecules of an ester undergo condensation, then it is called claisen condensation. Like in aldol reaction, in claisen condensation one molecule is a nucleophile and the other molecule is an electrophile.
A claisen condensation reaction is a reversible reaction and occurs in the presence of a strong base.
The first step of claisen condensation is the removal of a proton from alpha carbon by a base and then the addition of enolate ion formed to the second ester molecule forming a β-ketoester.
![Check Mark](/static/check-mark.png)
Trending nowThis is a popular solution!
![Blurred answer](/static/blurred-answer.jpg)
Chapter 19 Solutions
OWLv2 with MindTap Reader, 1 term (6 months) Printed Access Card for Brown/Iverson/Anslyn/Foote's Organic Chemistry, 8th Edition
- Provide a retrosynthetic pathway from the following compound. Indicate reagents needed for each transformation...arrow_forwardPlease give the appropriate reagents to complete the following synthesis.arrow_forwardProvide a synthesis for the following transformation. Ethyl acetoacetic ester and any other necessary reagentsarrow_forward
- Show how the following ketones might be synthesized from the indicated acids, usingany necessary reagents.(b) methyl cyclohexyl ketone from cyclohexanecarboxylic acidarrow_forwardShow how you would synthesize octanal from each compound. You may use any necessary reagents.(a) octan-1-olarrow_forwardLinalool (the Chapter 9 opening molecule) and lavandulol are two of the major components of lavender oil. (a) What organolithium reagent and carbonyl compound can be used to make each alcohol? (b) How might lavandulol be formed by reduction of a carbonyl compound? (c) Why can’t linalool be prepared by a similar pathway?arrow_forward
- β-Vetivone is isolated from vetiver, a perennial grass that yields a variety ofcompounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.arrow_forwardArrange each group of compounds in order of increasing acidity.(b) p-toluenesulfonic acid, acetic acid, chloroacetic acidarrow_forwardConsider carbonyl compounds A–E drawn below. (a) Rank A–E in order of increasing stability. (b) Rank A–E in order of increasing amount of hydrate formed when treated with aqueous acid. (c) Which compound is most reactive in nucleophilic addition?arrow_forward
- Acyclovir is an effective antiviral agent used to treat the herpes simplex virus. (a) Draw the enol form of acyclovir, and explain why it is aromatic. (b) Why is acyclovir typically drawn in its keto form, despite the fact that its enol is aromatic?arrow_forwardWhen trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels, at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.arrow_forwardWhen trichloroacetaldehyde is dissolved in water, almost all of it is converted to the hydrate. Chloral hydrate, the product of the reaction, is a sedative that can be lethal. A cocktail laced with it is known—in detective novels,at least—as a “Mickey Finn.” Explain why an aqueous solution of trichloroacetaldehyde is almost all hydrate.arrow_forward
- ChemistryChemistryISBN:9781305957404Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCostePublisher:Cengage LearningChemistryChemistryISBN:9781259911156Author:Raymond Chang Dr., Jason Overby ProfessorPublisher:McGraw-Hill EducationPrinciples of Instrumental AnalysisChemistryISBN:9781305577213Author:Douglas A. Skoog, F. James Holler, Stanley R. CrouchPublisher:Cengage Learning
- Organic ChemistryChemistryISBN:9780078021558Author:Janice Gorzynski Smith Dr.Publisher:McGraw-Hill EducationChemistry: Principles and ReactionsChemistryISBN:9781305079373Author:William L. Masterton, Cecile N. HurleyPublisher:Cengage LearningElementary Principles of Chemical Processes, Bind...ChemistryISBN:9781118431221Author:Richard M. Felder, Ronald W. Rousseau, Lisa G. BullardPublisher:WILEY
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305957404/9781305957404_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781259911156/9781259911156_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305577213/9781305577213_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9780078021558/9780078021558_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305079373/9781305079373_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781118431221/9781118431221_smallCoverImage.gif)