Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Textbook Question
Chapter 19, Problem 40P
When the aldol reaction of acetaldehyde is carried out in
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An enolate attacks an aldehyde and the resulting product is subsequently protonated. What
type of reaction is this?
an acid-catalyzed aldol condensation
a Fischer esterification.
a Grignard reaction.
a base-mediated aldol condensation
In an aldol condensation reaction, acetone and benzaldehyde are mixed in the presence of sodium hydroxide to produce dibenzalacetone. Does it matter whether the acetone is added first to the aq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone? Explain
Draw the aldol product for the reaction of the aldehyde shown with NaOH. Assume the reaction is run under conditions that allow the reaction to stop
before dehydration.
u
H
NaOH
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
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- (b) Why is the Claisen-Schmidt reaction a special type of aldol condensation? one of the reactants does not have a β hydrogen one of the reactants is acetone the reaction is base-catalyzed one of the reactants does not have an α hydrogen (b) Aside from having a carboxylic acid functional group, salicylic acid also has which of the following functionality? aldehyde alcohol ester phenolarrow_forwardBenzalacetone is a side product formed in the aldol condensation of dibenzalacetone. Show the reaction mechanism of how this side product, Benzalacetone, is formed.arrow_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_forward
- The Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a B-keto ester, an enamine, or a B-diketone) and an a,8-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. The above reaction between a enamine and an a,B-unsaturated ketone yields a product containing a 2-cyclohexenone ring. One of the steps of this reaction follows. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions H-A A OH HO Nest Emal Instructor Save and Exarrow_forwardThe Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-keto ester and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product: Draw the β-keto ester as an ethyl ester,arrow_forwardThe Robinson annulation is a combination of two carbonyl coupling reactions, the Michael reaction and the intramolecular aldol condensation. The most common partners in the reaction are a nucleophilic donor (such as a cyclic ketone, a β-keto ester, an enamine, or a β-diketone) and an α,β-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. Draw the structures of the nucleophilic β-diketone and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product:arrow_forward
- 2 H3C H3C H C→XT OH H3C The aldol reaction is a carbonyl condensation reaction between two carbonyl partners and involves a combination of nucleophilic addition and a-substitution steps. One partner is converted into an enolate ion nucleophile and adds to the electrophilic carbonyl group of the second partner. In the classic aldol reaction, the carbonyl partners are aldehydes or ketones, although aldehydes are more reactive. The product is a ß-hydroxy carbonyl compound. base :0: OH H H Under reaction conditions slightly more vigorous than those employed for the aldol reaction, the ß-hydroxyl group is eliminated in an E1cB dehydration to give an a,ß-unsaturated carbonyl compound. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instruct ns H3C heat OH H3C :0: H + H₂O Harrow_forwardConsider the following reactions, and draw the products that are formed. Part 1 of 2 Draw the structure of the aldol condensation product that results from dimerization of the following aldehyde. You do not need to show stereochemistry. H* or HO H₂O Click and drag to start drawing a structure. × D: G P Part 2 of 2 Draw the structure of the aldol condensation product that results from dimerization of the following aldehyde. You do not need to show stereochemistry. H H+ or HO H₂O Click and drag to start drawing a structure. D: X 5 。arrow_forwardAldol reactions provide another way to build longer or branched carbon chains. Write a retro- synthetic reaction plan for preparation of this compound using a base-catalyzed aldol reaction or condensation. What base should be used to generate the enolate required for this reaction? Is the enolate a kinetic enolate or a thermodynamic enolate? محدد OH . Using the starting material for synthesis of the compound shown above, another aldol product is possible. Write the reaction to show formation of the other possible product. Assume base catalysis.arrow_forward
- Write the complete mechanism for the hydroxide ion catalyze reaction of cyclohexanone and 1-methylcyclohexanecarbaldehydearrow_forward3,4-dimethoxylbenzaldehyde reacts with 1-indanone to form what product in an Aldol-condensation reaction?arrow_forwardThe overall reaction produced by the aldol condensation of acetophenone and benzaldehyde is shown below. + NaOH, A Acetophenone Benzaldehyde Chalcone Which of the following steps are involved in the mechanism that leads to the formation of chalcone? он + он H OH он + Он OH + Тон Он он + + Он ОН + онarrow_forward
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