Organic Chemistry
11th Edition
ISBN: 9781118133576
Author: T. W. Graham Solomons, Craig Fryhle
Publisher: Wiley, John & Sons, Incorporated
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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 - 19.50 (+)-Fenchone is a terpenoid that can be...Ch. 19 - Prob. 51PCh. 19 - Prob. 52PCh. 19 - Prob. 53PCh. 19 - Prob. 54PCh. 19 - The Perkin condensation is an aldol-type...Ch. 19 - 19.55 (a) Infrared spectroscopy provides an easy...Ch. 19 - Prob. 57PCh. 19 - 19.61 Provide a mechanism for each of the...Ch. 19 - 19.62 (a) Deduce the structure of product A,...Ch. 19 - 19.60 Write the structures of the three products...Ch. 19 - Prob. 1LGPCh. 19 - Which hydrogen atoms in the following ester are...Ch. 19 - Prob. 2QCh. 19 - 19.3 What starting materials could be used in a...Ch. 19 - Supply the missing reagents, intermediates, and...Ch. 19 - Prob. 5QCh. 19 - Prob. 6QCh. 19 - Prob. 7QCh. 19 - Prob. 8Q
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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_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_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
- 1. 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_forwardThe by-product of the aldol reaction has not been drawn in this diagram. What is it?arrow_forwardAldol Condensation- Synthesis of Dibenzalacetone The protocol says that, after adding in all the reactants, stir for an additional 15 minutes. A student swirled for only 8 minutes and then, correctly, stopped and proceeded with isolating the product. What did the student do that gave such confidence and accuracy?arrow_forward
- When performing a crossed Aldol reaction, the order of addition of reactants is important. What would happen if sodium hydroxide was mixed with acetone first, then anisaldehyde was added. Draw 2 potential unwanted byproducts. Assume the product spontaneously dehydrates.arrow_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_forwardDefine Dehydration of the Aldol Product ?arrow_forward
- Vanillin has an acidic OH and an electrophilic aldehyde group that could conceivably react with sodiumhydroxide. However, in the aldol reaction, you added the NaOH directly to the solution of vanillin andacetone, rather than pre-treating acetone with base. Why could you do this successfully? a) NaOH is a weak base and a weak nucleophile.b) The reaction of NaOH with phenol OH groups and aromatic aldehydes is reversible, and thereaction is driven to the most stable product.c) The aldehyde in vanillin is unreactive towards nucleophiles.d) The NaOH is not soluble in the reactionarrow_forwardWrite the complete mechanism for the hydroxide ion catalyze reaction of cyclohexanone and 1-methylcyclohexanecarbaldehydearrow_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 ß-keto ester, an enamine, or a ß-diketone) and an a,ß-unsaturated ketone acceptor. The product is a substituted 2-cyclohexenone derivative. il The above reaction between a ß-keto ester and an a,ß-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 AC↔XT я OEt -I H OEt CO₂Et Eto: يز OEt EtOHarrow_forward
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