Organic Chemistry
12th Edition
ISBN: 9781118875766
Author: T. W. Graham Solomons, Craig B. Fryhle, Scott A. Snyder
Publisher: WILEY
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Chapter 19, Problem 40P
When the aldol reaction of acetaldehyde is carried out in
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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
phenol
Benzalacetone is a side product formed in the aldol condensation of dibenzalacetone. Show the reaction mechanism of how this side product, Benzalacetone, is formed.
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
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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- 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? Explainarrow_forwardWhat is the mechanism for this Aldol reaction?arrow_forwardDraw the product formed (after dehydration) in the crossed aldol condensation of phenylacetaldehyde (C6H5CH2CHO) with CH2(CO2Et)2 in the presence of sodium hydroxide.arrow_forward
- Draw the structure of the aldol that will form when cyclohexanone reacts with one mole ofbenzaldehyde. What is the name of this compound?arrow_forwardIdentify the major aldol condensation product obtained when the following compound is heated in the presence of aqueous sodium hydroxide.arrow_forward1. An aldol reaction begins with addition of a catalytic amount of base to an aldehyde or ketone. Write the first step (formation of an enolate) of the reaction when a catalytic amount of NaOH is added to acetaldehyde. Base HH Z H 2. Continue the reaction in problem 1 showing reaction of the enolate with an unaffected molecule of acetaldehyde forming an alkoxide. Subsequent reaction with water yields a B-hydroxyaldehyde. OH -=7 H base H OH o ния H H टे H alo C The overall reaction in problems 1 and 2 is an aldol addition reaction. Each step is reversible. Write the mechanism for the reverse process converting the B-hydroxyaldehyde into two molecules of the original aldehyde. This process is a retro-aldol reaction. Use pK, values to explain why the process is reversible. -OH- e 7L Hlobia. Write the mechanism for reaction of butanone with catalytic aqueous NaOH. (Show each step with a reversible reaction arrow.)arrow_forward
- The first step of the dimedone reaction involves an aldol reaction. Here is a simpler version - which of the molecules shown is the product from this aldol reaction?arrow_forward2 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_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_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-diketone and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product:arrow_forwardGive the structures of the aldol products that form when each of the following compounds or mixtures is treated with NaOH. The top three compounds are aldol dimerizations and require 2 moles of the reactant listed, while the two compounds on the bottom row are being used in a mixed aldol reaction. Butanal, Cyclopentanone, and Acetophenone (PhCOCH3) p-chlorobenzaldehyde and 2,2-dimethylcyclohexanonearrow_forward
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