EP ORGANIC CHEMISTRY-OWL V2 ACCESS
8th Edition
ISBN: 9781305582453
Author: Brown
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 19.6, Problem 19.11P
Interpretation Introduction
Interpretation:
The conversion of ethyl 2-oxocyclopentanecarboxylate to the given compound 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.
Expert Solution & Answer
![Check Mark](/static/check-mark.png)
Want to see the full answer?
Check out a sample textbook solution![Blurred answer](/static/blurred-answer.jpg)
Students have asked these similar questions
Optically active 2-iodobutaneslowly becomes racemic when treated with sodium iodide in an inert polar solvent. Explain why
Optically active 2-iodooctane slowly becomes racemic when treated with sodium iodide in an inert polar solvent. Explain why
When norbornene undergoes hydroboration-oxidation, a mixture of two stereoisomers is produced in a roughly 6:1 ratio.
(a) Draw both of these isomeric products. (b) Which product is favored? Hint: You should build a model of norbornene
and consider the transition state leading to each product.
1. BH3 THF
?
2. H2O2, NaOH, H,O
Norbornene
Chapter 19 Solutions
EP ORGANIC CHEMISTRY-OWL V2 ACCESS
Ch. 19.2 - Prob. 19.1PCh. 19.2 - Prob. 19.2PCh. 19.2 - Prob. 19.3PCh. 19.3 - Prob. 19.4PCh. 19.3 - Prob. 19.5PCh. 19.3 - Prob. 19.6PCh. 19.5 - Prob. 19.7PCh. 19.5 - Prob. 19.8PCh. 19.5 - Prob. 19.9PCh. 19.6 - Prob. 19.10P
Ch. 19.6 - Prob. 19.11PCh. 19.7 - Prob. 19.12PCh. 19.8 - Prob. 19.13PCh. 19.8 - Prob. 19.14PCh. 19.8 - Prob. 19.15PCh. 19.8 - Prob. 19.16PCh. 19.9 - Prob. 19.17PCh. 19.9 - Prob. AQCh. 19.9 - Prob. BQCh. 19.9 - Prob. CQCh. 19.9 - Prob. DQCh. 19.9 - Prob. EQCh. 19.9 - Prob. FQCh. 19.9 - Prob. GQCh. 19.9 - Intermediate G in Synthesis III is produced as a...Ch. 19.9 - Prob. IQCh. 19.9 - Prob. JQCh. 19 - Prob. 19.18PCh. 19 - Prob. 19.19PCh. 19 - Prob. 19.20PCh. 19 - Prob. 19.21PCh. 19 - Prob. 19.22PCh. 19 - Prob. 19.23PCh. 19 - Cyclohexene can be converted to...Ch. 19 - Prob. 19.25PCh. 19 - Prob. 19.26PCh. 19 - Prob. 19.27PCh. 19 - Prob. 19.28PCh. 19 - Prob. 19.29PCh. 19 - Prob. 19.30PCh. 19 - Draw structural formulas for the -ketoesters...Ch. 19 - Prob. 19.32PCh. 19 - Prob. 19.33PCh. 19 - Propose a synthesis for each ketone, using as one...Ch. 19 - Prob. 19.35PCh. 19 - Claisen condensation between diethyl phthalate and...Ch. 19 - Prob. 19.37PCh. 19 - Prob. 19.38PCh. 19 - Prob. 19.39PCh. 19 - Enamines normally react with methyl iodide to give...Ch. 19 - Prob. 19.41PCh. 19 - Prob. 19.42PCh. 19 - Prob. 19.43PCh. 19 - Prob. 19.44PCh. 19 - Prob. 19.45PCh. 19 - Prob. 19.46PCh. 19 - Prob. 19.47PCh. 19 - Prob. 19.48PCh. 19 - Prob. 19.49PCh. 19 - Prob. 19.50PCh. 19 - Prob. 19.51PCh. 19 - Prob. 19.52PCh. 19 - Show experimental conditions by which to carry out...Ch. 19 - Prob. 19.55PCh. 19 - The compound 3,5,5-trimethyl-2-cyclohexenone can...Ch. 19 - Prob. 19.57PCh. 19 - Prob. 19.58PCh. 19 - The widely used anticoagulant warfarin (see...Ch. 19 - Following is a retrosynthetic analysis for an...Ch. 19 - Following are the steps in one of the several...Ch. 19 - Prob. 19.62PCh. 19 - Prob. 19.63PCh. 19 - Prob. 19.65PCh. 19 - Prob. 19.67PCh. 19 - Prob. 19.68PCh. 19 - Prob. 19.69PCh. 19 - In Problem 7.28, we saw this two-step sequence in...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Using your reaction roadmaps as a guide, show how...Ch. 19 - Prob. 19.79PCh. 19 - Prob. 19.80PCh. 19 - Prob. 19.81PCh. 19 - The following molecule undergoes an intramolecular...
Knowledge Booster
Similar questions
- In contrast, optically active butan-2-ol does not racemize on treatment with a solution of KOH. Explain why a reaction like that does not occur?arrow_forwardAcid-catalyzed bromination of pentan-2-one (CH3COCH2CH2CH3) forms two products: BrCH2COCH2CH2CH3 (A)and CH3COCH(Br)CH2CH3 (B). Explain why the major product is B, with the Br atom on the more substituted side of the carbonyl group.arrow_forwardProvide the products for the reactions, including the appropriate stereochemistry. 1) O3 i) 2) DMS H2 ii) Pdarrow_forward
- Predict the favored product of each of the following reduction reactions. If the product is chiral, draw both stereoisomers expected. (b) NaBD4 CH3CH₂OH NaBH4 CH3CH₂OHarrow_forwardElimination occurs when (Z)-3-bromohex-3-ene is treated with NaNH2. Under the same conditions, 1-bromocyclohexeneundergoes elimination much more sluggishly. Explain whyarrow_forwardCyclohexanone do not produce isomeric oximes but cyclohexane does produces 2 stereoisomeric oximes. Explain whyarrow_forward
- give the major products of this reaction. include stereochemistry as appropiate. strongly appreciate it.arrow_forwardWhen compound (A) is treated with Cl-, the result is (B), as shown at the right. You might want to number your carbons. Just sayin'. RO When 2-(2-hydroxyhept-6-en-2-yl)phenol (C) is treated with aqueous acid, the result is 6,7-benzo-1,5-dimethyl-8-oxabicyclo[4.3.1]nonane (D), as shown at the right. You might want to number your carbons. Just sayin'. -N (A) Give a detailed, stepwise mechanism that accounts for the formation of (B) from (A). OTf Give a detailed, stepwise mechanism that accounts for the formation of (D) from (C). CH,Ph OH OH (C) CI RO H3O* N. (B) CH₂CI CH,Ph (D) + OTfarrow_forwardCompound A has the formula C5H10O that is produced by oxidation of a conpound that has the formula C5H12O. Compound A has an IT spectrum the has an absorbance at 1700 cm^-1 and no broad absorbance from 2500-3500 cm^-1. The 1H and 13C spectrums of Compound A both have 4 peaks. What is tbe structure of Compound A? Thank you for the help!arrow_forward
- Drawing the Products of Hydroboration-Oxidation Draw the product of the following reaction sequence, including stereochemistry.arrow_forwardDraw the major organic product of the following reaction. + PC13arrow_forwardDraw a structure for the product of nucleophilic substitution obtained on solvolysis of tert-butyl bromide in methanol, and arrange the correct mechanism for its formation. Be sure to answer all parts.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 LearningEBK A SMALL SCALE APPROACH TO ORGANIC LChemistryISBN:9781305446021Author:LampmanPublisher:CENGAGE LEARNING - CONSIGNMENT
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305580350/9781305580350_smallCoverImage.gif)
Organic Chemistry
Chemistry
ISBN:9781305580350
Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote
Publisher:Cengage Learning
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305080485/9781305080485_smallCoverImage.gif)
![Text book image](https://www.bartleby.com/isbn_cover_images/9781305446021/9781305446021_smallCoverImage.jpg)
EBK A SMALL SCALE APPROACH TO ORGANIC L
Chemistry
ISBN:9781305446021
Author:Lampman
Publisher:CENGAGE LEARNING - CONSIGNMENT