Organic Chemistry As a Second Language: Second Semester Topics
4th Edition
ISBN: 9781119110651
Author: David R. Klein
Publisher: WILEY
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Chapter 8.7, Problem 8.42P
Interpretation Introduction
Interpretation:
Reagents that are used to prepare the given compound using aldol condensation has to be identified.
Concept Introduction:
Formation of
If the above method is reversed, then the reagents that are required can be identified.
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Draw the organic reagent(s) necessary to synthesize the following compound by
an aldol condensation.
OH
Which of the following can undergo an aldol self-condensation and yield multiple
(different) self-condensation products?
A
H₂
H3C
g
CH3
H
B
D
H₂
se
H₂
H3C
H3C
CH3
H
Describe how the following compound can be prepared using an aldol addition in the first step of the synthesis:
Chapter 8 Solutions
Organic Chemistry As a Second Language: Second Semester Topics
Ch. 8.1 - For each of the compounds below, identify all...Ch. 8.1 - For each of the compounds below, identify all...Ch. 8.1 - For each of the compounds below, identify all...Ch. 8.1 - For each of the compounds below, identify all...Ch. 8.1 - For each of the compounds below, identify all...Ch. 8.1 - For each of the compounds below, identify all...Ch. 8.2 - Prob. 8.9PCh. 8.2 - Prob. 8.10PCh. 8.2 - Prob. 8.11PCh. 8.2 - Prob. 8.12P
Ch. 8.2 - Prob. 8.13PCh. 8.3 - Predict the products of each of the following...Ch. 8.3 - Predict the products of each of the following...Ch. 8.3 - Predict the products of each of the following...Ch. 8.3 - Predict the products of each of the following...Ch. 8.4 - Prob. 8.20PCh. 8.4 - Prob. 8.21PCh. 8.4 - Prob. 8.22PCh. 8.4 - Prob. 8.23PCh. 8.5 - Prob. 8.25PCh. 8.5 - Prob. 8.26PCh. 8.5 - On a separate piece of paper, draw a mechanism for...Ch. 8.6 - Prob. 8.29PCh. 8.6 - Predict the major product for each of the...Ch. 8.6 - Predict the major product for each of the...Ch. 8.6 - Predict the major product for each of the...Ch. 8.6 - Identify the reagents you would use to achieve...Ch. 8.6 - Identify the reagents you would use to achieve...Ch. 8.6 - Identify the reagents you would use to achieve...Ch. 8.7 - Predict the major product for each of the...Ch. 8.7 - Predict the major product for each of the...Ch. 8.7 - Predict the major product for each of the...Ch. 8.7 - Prob. 8.42PCh. 8.7 - Prob. 8.43PCh. 8.7 - Prob. 8.44PCh. 8.7 - Prob. 8.45PCh. 8.7 - Prob. 8.47PCh. 8.7 - Prob. 8.48PCh. 8.7 - Prob. 8.49PCh. 8.7 - Prob. 8.50PCh. 8.8 - Prob. 8.52PCh. 8.8 - Prob. 8.53PCh. 8.8 - Prob. 8.54PCh. 8.8 - Prob. 8.55PCh. 8.8 - Prob. 8.57PCh. 8.8 - Prob. 8.58PCh. 8.8 - Prob. 8.59PCh. 8.8 - Prob. 8.60PCh. 8.8 - Propose a mechanism for each of the following...Ch. 8.8 - Propose a mechanism for each of the following...Ch. 8.8 - Prob. 8.64PCh. 8.9 - Prob. 8.66PCh. 8.9 - Prob. 8.67PCh. 8.9 - Prob. 8.68PCh. 8.9 - Prob. 8.69PCh. 8.9 - Prob. 8.70PCh. 8.9 - Prob. 8.71PCh. 8.9 - Prob. 8.72PCh. 8.9 - Identify what reagents you would use to achieve...Ch. 8.9 - Identify what reagents you would use to achieve...Ch. 8.9 - Identify what reagents you would use to achieve...Ch. 8.10 - Prob. 8.78PCh. 8.10 - Prob. 8.79PCh. 8.10 - Prob. 8.80PCh. 8.10 - Propose a synthesis for each of the following...Ch. 8.10 - Propose a synthesis for each of the following...Ch. 8.10 - Propose a synthesis for each of the following...Ch. 8.10 - Propose a synthesis for each of the following...
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- Identify the bonds in the compound below could be synthesized using an aldol reaction or aldol condensation. HO A B C A E F G H K O OH C LE B D F OH G Harrow_forwardThe following molecule can be formed via an intramolecular aldol addition reaction. Draw the organic starting material needed to form the given B-hydroxycarbonyl compound. organic starting material B-hydroxycarbonyl NaOH OHarrow_forwardProvide the reagents necessary to affect each transformationarrow_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_forwardDescribe how the following compound can be prepared using an aldol addition in the first step of the synthesis:arrow_forwardDraw the major organic product(s) for the following reactionarrow_forward
- base H3C H OH heat H + H₂O H 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. In the mixed aldol reaction, the best results are obtained when one of the partners does not have an a-hydrogen. It cannot form an enolate anion and can therefore not undergo self-reaction. The enolizable aldehyde is added slowly to a basic solution of the first aldehyde so that the mixed product is preferentially formed. 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.…arrow_forwardShow how to prepare a,b-unsaturated ketone by an aldol reaction followed by dehydration of the aldol product.arrow_forwardThe first steps in the synthesis of azelnidipine, a calcium channel blocker, involves the reaction of β-keto ester A with aldehyde B in the presence of base. What crossed aldol product is formed in this reaction?arrow_forward
- Show how to prepare a,b-unsaturated aldehyde by an aldol reaction followed by dehydration of the aldol product.arrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an α,β-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of formation of an enamine from a ketone, Michael addition to an α,β-unsaturated carbonyl compound, and hydrolysis of the enamine in dilute acid to regenerate the ketone. Consider the Stork reaction between acetophenone and 3-buten-2-one. Draw the structure of the product of the enamine formed between acetophenone and pyrrolidine. Draw the structure of the Michael addition product. Draw the structure of the final product.arrow_forwardPropose a mechanism for the reaction of benzyl acetate with methylamine. Label theattacking nucleophile and the leaving group, and draw the transition state in which theleaving group leaves.arrow_forward
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