ORGANIC CHEM.-S.M.+STD.GDE(LL)-W/ACCESS
8th Edition
ISBN: 9780134777658
Author: Bruice
Publisher: PEARSON
expand_more
expand_more
format_list_bulleted
Concept explainers
Textbook Question
Chapter 17, Problem 60P
Using cyclopentanone as the reactant, show the product of
a. acid-catalyzed keto-enol interconversion.
b. an aldol addition.
c. an aldol condensation.
Expert Solution & Answer
Want to see the full answer?
Check out a sample textbook solutionStudents have asked these similar questions
All are true or false
a) The initially formed b-hydroxy carbonyl compound loses water in a Aldol condensation.
b) Equilibrium favors the starting materials with both aldehydes and ketones for Aldol reactions.
c)The Claisen reaction is a type of nucleophilic addition?
d) The b-hydroxy carbonyl product of an Aldol reaction is oftentimes not the final isolated product.
e)b-Ketoester and an enolate are the two starting materials for a Robinson annulation
Aldol Condensation
What products are formed?
What is the difference between aldol reactions and aldol condensation?
What type of reaction condentionas are used?
Use the appropriate reagent used in the reaction.
(d),(e) please!!
Chapter 17 Solutions
ORGANIC CHEM.-S.M.+STD.GDE(LL)-W/ACCESS
Ch. 17.1 - Prob. 1PCh. 17.1 - Prob. 2PCh. 17.1 - Prob. 3PCh. 17.1 - Prob. 4PCh. 17.1 - Rank the compounds in each of the following groups...Ch. 17.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 17.3 - Draw the enol tautomers for each of the following...Ch. 17.3 - Prob. 8PCh. 17.4 - Prob. 9PCh. 17.4 - Prob. 10P
Ch. 17.5 - Show how the following compounds can be prepared...Ch. 17.6 - What compound is formed when a dilute solution of...Ch. 17.7 - Prob. 13PCh. 17.7 - Prob. 14PCh. 17.7 - How many stereoisomers are obtained from each of...Ch. 17.7 - Prob. 16PCh. 17.8 - Prob. 17PCh. 17.9 - Prob. 18PCh. 17.9 - What reagents should be used to prepare the...Ch. 17.10 - Prob. 20PCh. 17.10 - What aldehyde or ketone would be obtained when...Ch. 17.11 - Prob. 22PCh. 17.11 - How could you prepare the following compound using...Ch. 17.12 - Prob. 25PCh. 17.12 - What two carbonyl compound are required for the...Ch. 17.12 - Propose a mechanism for the following reaction:Ch. 17.13 - Draw the products of the following reactions:Ch. 17.13 - Prob. 29PCh. 17.13 - Prob. 30PCh. 17.14 - Prob. 31PCh. 17.15 - Write the mechanism for the reaction of a...Ch. 17.15 - Prob. 33PCh. 17.15 - Prob. 34PCh. 17.15 - Draw the product of the reaction of each of the...Ch. 17.16 - Draw the product obtained by heating each pair of...Ch. 17.16 - What two carbonyl compounds are needed to...Ch. 17.17 - Prob. 38PCh. 17.18 - Prob. 39PCh. 17.18 - Prob. 40PCh. 17.19 - Prob. 41PCh. 17.20 - Prob. 43PCh. 17.21 - Propose a mechanism for the formation of...Ch. 17.21 - Prob. 45PCh. 17.21 - a. If the biosynthesis of palmitic acid were...Ch. 17.21 - Prob. 47PCh. 17 - Prob. 48PCh. 17 - Prob. 49PCh. 17 - Number the following compounds in order of...Ch. 17 - The 1H NMR chemical shifts of nitromethane,...Ch. 17 - Prob. 52PCh. 17 - Draw the products of the following reactions: a....Ch. 17 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 17 - Draw the products of the following reaction:Ch. 17 - Prob. 56PCh. 17 - Prob. 57PCh. 17 - In the presence of excess base and excess halogen,...Ch. 17 - Identify A-L. (Hint: A shows three singles in its...Ch. 17 - Using cyclopentanone as the reactant, show the...Ch. 17 - Show how 4-methyl-3-hexanol can be synthesized...Ch. 17 - Show how the following compound can be synthesized...Ch. 17 - Show how the following compounds can be prepared...Ch. 17 - Prob. 64PCh. 17 - Prob. 65PCh. 17 - Indicate how each of the following compounds can...Ch. 17 - Prob. 67PCh. 17 - The ketone whose 1H NMR spectrum is shown here was...Ch. 17 - Indicate how the following compounds can be...Ch. 17 - Compound A with molecular formula C6H10 has two...Ch. 17 - Prob. 71PCh. 17 - Draw the products of the following reactions:Ch. 17 - Prob. 73PCh. 17 - a. Show how the amino acid alanine can be...Ch. 17 - Show how the following compounds can be...Ch. 17 - Prob. 76PCh. 17 - Explain why the following bromoketone forms...Ch. 17 - Prob. 78PCh. 17 - A carboxylic arid is formed when an -haloketone...Ch. 17 - An , -unsaturated carbonyl compound can be...Ch. 17 - What carbonyl compounds are required to prepare a...Ch. 17 - Prob. 82PCh. 17 - A Cannizzaro reaction is the reaction of an...Ch. 17 - Propose a mechanism for each of the following...Ch. 17 - The following reaction is known as the benzoni...Ch. 17 - Prob. 86PCh. 17 - Prob. 87PCh. 17 - Prob. 88PCh. 17 - Prob. 89PCh. 17 - Prob. 90PCh. 17 - Propose a mechanism for the following reaction:Ch. 17 - What reagents are required to convert the reactant...Ch. 17 - Starting with bromocyclohexane, how can each of...Ch. 17 - Describe how the following compounds can be...Ch. 17 - Prob. 4PCh. 17 - Describe three ways to synthesize the following...Ch. 17 - Explain why 92% of 2.4-pentanedione exists as the...Ch. 17 - Describe how the following compound can be...Ch. 17 - Prob. 8PCh. 17 - Prob. 9PCh. 17 - Prob. 10PCh. 17 - Show how the following compounds can be...
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
- show the reaction scheme reagents and intermediatearrow_forwardThe aldol double condensation reaction is highly selective for formation of a single double condensation product. Explain why only one aldol condensation product is formed despite two carbonyl compounds being present for the reaction.arrow_forwardWhen performing a Grignard reaction it is also very important that the reaction be free from acetone (a chemical we commonly use to clean the glassware). Why must the glassware be free from acetone? A. Acetone reacts with the diethyl ether causing a side reaction to occur B. Acetone is a nucleophile that will react with the Grignard reagent C. Acetone reacts with the bromobenzene D. Acetone is an electrophile that will react with the Grignard reagentarrow_forward
- Define Dehydration of the Aldol Product ?arrow_forwardWhat is the best combination to create a beta-dicarbonyl (1,3-dicarbonyl) compound? a) enolate + aldehyde b) enolate + acid derivative c) enolate + alpha-halogenated carbonyl d) enolate + conjugated carbonyl (Michael addition)arrow_forward5. WHAT IS GRIGNARD REACTION? WHAT CONSTITUTES A GRIGNARD REAGENT? 6. WHAT IS KETO-ENOL TAUTOMERIZATION?arrow_forward
- for the theroretical yield is the mol correct? also using the aldol condensation reaction in this portion are we using the aldol condensation reaction to synthesize acetophenone and para-methybenzaldehye. acetophenone 0.5 g, 4.2 mmol Para-methylbenzaldehyde 0.5 g, 4.2 mmol NaOH=0.18g = 4.5 mol Theroretical yield=0.93g =0.0519 mol Percent yield=76.8% Actual yield= 0.715 g Melting point observered= 93 degree Celsius Expected melting point =93-94.5 degree Celsiusarrow_forwardAcetal product formation requires an acid catalyst in the second step, but NOT in the first step. True or False?arrow_forwardWhich statement describes why aldol reactions with ketones are low yielding? A.Ketones do not have acidic protons. B.Ketones are too electron poor at the carbonyl carbon. C.Ketones can attack other ketones well but perform poorly in self-condensations. D.The product of a ketone addition to a ketone has considerable steric strain.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning
Organic Chemistry: A Guided Inquiry
Chemistry
ISBN:9780618974122
Author:Andrei Straumanis
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