Organic Chemistry
7th Edition
ISBN: 9780321803221
Author: Paula Y. Bruice
Publisher: Prentice Hall
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Textbook Question
Chapter 18, Problem 59P
Using cyclopentanone as the reactant, show the product of
a. acid-catalyzed keto-enol interconversion.
b. an aldol addition.
c. an aldol condensation.
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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 18 Solutions
Organic Chemistry
Ch. 18.1 - Prob. 1PCh. 18.1 - Prob. 2PCh. 18.1 - Prob. 3PCh. 18.1 - Prob. 4PCh. 18.1 - PROBLEM 5♦
List the compounds in each of the...Ch. 18.2 - Explain why 92% of 2,4-pemtanedione exists as the...Ch. 18.3 - Draw the enol tautomers for each of the following...Ch. 18.3 - Prob. 8PCh. 18.4 - Prob. 9PCh. 18.4 - Prob. 10P
Ch. 18.5 - Show how the following compounds can be prepared...Ch. 18.6 - What compound is formed when a dilute solution of...Ch. 18.7 - Prob. 13PCh. 18.7 - Prob. 14PCh. 18.7 - How many stereoisomers are obtained from each of...Ch. 18.7 - Prob. 16PCh. 18.8 - Prob. 17PCh. 18.9 - Prob. 18PCh. 18.9 - Prob. 19PCh. 18.10 - Prob. 20PCh. 18.10 - What aldehyde or ketone would be obtained when...Ch. 18.11 - Prob. 22PCh. 18.12 - Prob. 24PCh. 18.12 - What two carbonyl compound are required for the...Ch. 18.12 - Propose a mechanism for the following reaction:Ch. 18.13 - Draw the products of the following reactions:Ch. 18.13 - Prob. 28PCh. 18.13 - Prob. 29PCh. 18.14 - Prob. 30PCh. 18.15 - Write the mechanism for the reaction of a...Ch. 18.15 - Prob. 32PCh. 18.15 - Prob. 33PCh. 18.15 - Draw the product of the reaction of each of the...Ch. 18.16 - Draw the product obtained by heating each pair of...Ch. 18.16 - Prob. 36PCh. 18.17 - Prob. 37PCh. 18.18 - Prob. 38PCh. 18.18 - Prob. 39PCh. 18.19 - Prob. 40PCh. 18.20 - Prob. 42PCh. 18.21 - Propose a mechanism for the formation of...Ch. 18.21 - Prob. 44PCh. 18.21 - a. If the biosynthesis of palmitic acid were...Ch. 18.21 - Prob. 46PCh. 18 - Prob. 47PCh. 18 - Prob. 48PCh. 18 - Number the following compounds in order of...Ch. 18 - The 1H NMR chemical shifts of nitromethane,...Ch. 18 - Prob. 51PCh. 18 - Draw the products of the following reactions: a....Ch. 18 - A racemic mixture of 2-methyl-1-phenyl-1-butanone...Ch. 18 - Prob. 54PCh. 18 - Prob. 55PCh. 18 - Prob. 56PCh. 18 - Prob. 57PCh. 18 - Identify A-L. (Hint: A shows three singles in its...Ch. 18 - Using cyclopentanone as the reactant, show the...Ch. 18 - Show how the following compounds can be prepared...Ch. 18 - Prob. 61PCh. 18 - Prob. 62PCh. 18 - Prob. 63PCh. 18 - The ketone whose 1H NMR spectrum is shown here was...Ch. 18 - Prob. 65PCh. 18 - Compound A with molecular formula C6H10 has two...Ch. 18 - Indicate how each of the following compounds can...Ch. 18 - Draw the products of the following reactions:Ch. 18 - Prob. 69PCh. 18 - a. Show how the amino acid alanine can be...Ch. 18 - Prob. 71PCh. 18 - Show how the following compounds can be...Ch. 18 - Explain why the following bromoketone forms...Ch. 18 - Prob. 74PCh. 18 - What carbonyl compounds are required to prepare a...Ch. 18 - Prob. 76PCh. 18 - A carboxylic arid is formed when an -haloketone...Ch. 18 - An , -unsaturated carbonyl compound can be...Ch. 18 - Prob. 79PCh. 18 - A Cannizzaro reaction is the reaction of an...Ch. 18 - Propose a mechanism for each of the following...Ch. 18 - The following reaction is known as the benzoni...Ch. 18 - Prob. 83PCh. 18 - Prob. 84PCh. 18 - Prob. 85PCh. 18 - Prob. 86PCh. 18 - Propose a mechanism for the following reaction:
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- 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
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