Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
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Chapter 23.SE, Problem 43MP
Interpretation Introduction
Interpretation:
The two steps, an intramolecular aldol reaction and retro aldol like reaction, involved in the reaction along with their mechanisms are to be given.
Concept introduction:
The steps involved are i) Deprotonation by the base ii) An intramolecular aldol reaction iii) A retro aldol reaction and iv) Protonation.
To give:
The two steps, an intramolecular aldol reaction and retro aldol like reaction, involved in the reaction along with their mechanisms.
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Chapter 23 Solutions
Organic Chemistry
Ch. 23.1 - Prob. 1PCh. 23.1 - Prob. 2PCh. 23.3 - Prob. 3PCh. 23.3 - Prob. 4PCh. 23.4 - Prob. 5PCh. 23.4 - 1-Butanol is prepared commercially by a route that...Ch. 23.4 - Prob. 7PCh. 23.5 - Prob. 8PCh. 23.6 - Prob. 9PCh. 23.6 - What product would you Expect to obtain from base...
Ch. 23.7 - Show the products you would expect to obtain by...Ch. 23.7 - Prob. 12PCh. 23.8 - What product would you expect from the following...Ch. 23.9 - What product would you expect From the following...Ch. 23.9 - Prob. 15PCh. 23.10 - Prob. 16PCh. 23.10 - Prob. 17PCh. 23.10 - Prob. 18PCh. 23.11 - Prob. 19PCh. 23.11 - Show how you might use an enamine reaction to...Ch. 23.12 - Prob. 21PCh. 23.12 - How would you prepare the following compound using...Ch. 23.SE - Prob. 23VCCh. 23.SE - Prob. 24VCCh. 23.SE - Prob. 25VCCh. 23.SE - The following molecule was formed by a Robinson...Ch. 23.SE - Prob. 27MPCh. 23.SE - Prob. 28MPCh. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Predict the product(s) and provide the mechanism...Ch. 23.SE - Knoevenagel condensation is a reaction involving...Ch. 23.SE - Azlactones are important starting materials used...Ch. 23.SE - Prob. 34MPCh. 23.SE - Isoleucine, another of the twenty amino acids...Ch. 23.SE - The first step in the citric acid cycle of food...Ch. 23.SE - Prob. 37MPCh. 23.SE - The Knoevenagel reaction is a carbonyl...Ch. 23.SE - The Darzens reaction invoIves a two-step,...Ch. 23.SE - The following reaction involves a hydrolysis...Ch. 23.SE - Prob. 41MPCh. 23.SE - Prob. 42MPCh. 23.SE - Prob. 43MPCh. 23.SE - Propose a mechanism for the following...Ch. 23.SE - Prob. 45MPCh. 23.SE - Prob. 46MPCh. 23.SE - Prob. 47MPCh. 23.SE - Prob. 48APCh. 23.SE - Prob. 49APCh. 23.SE - Prob. 50APCh. 23.SE - Prob. 51APCh. 23.SE - Prob. 52APCh. 23.SE - Prob. 53APCh. 23.SE - Prob. 54APCh. 23.SE - Prob. 55APCh. 23.SE - Prob. 56APCh. 23.SE - Prob. 57APCh. 23.SE - Prob. 58APCh. 23.SE - In the mixed Claisen reaction of cyclopentanone...Ch. 23.SE - Ethyl dimethylacetoacetate reacts instantly at...Ch. 23.SE - Prob. 61APCh. 23.SE - Prob. 62APCh. 23.SE - The so-called Wieland-Miescher ketone is a...Ch. 23.SE - Prob. 64APCh. 23.SE - Prob. 65APCh. 23.SE - Prob. 66APCh. 23.SE - What condensation products would you expect to...Ch. 23.SE - The following reactions are unlikely to provide...Ch. 23.SE - Fill in the missing reagents a-h in the following...Ch. 23.SE - Prob. 70APCh. 23.SE - Prob. 71APCh. 23.SE - Prob. 72APCh. 23.SE - Prob. 73AP
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- Show how to prepare a,b-unsaturated ketone by an aldol reaction followed by dehydration of the aldol product.arrow_forwardWhen the ketone and aldehyde shown below are treated with a base two possible products are formed. Discuss how each product is formed and provide a mechanism.arrow_forwardWhat reagents are required to carry out the following synthesis?arrow_forward
- The following synthesis requires more than one step. Specify the reagents you would use to carry it out.arrow_forwardDraw the structures A, B and C for the reaction sequence below. Dehydration via an E1cb mechanism Michael Reaction Intramolecular Aldol Reaction A В КОН /ETOH / heat C КОН /ETOH КОН /ETOHarrow_forwardWhat reagents ( A–D) are needed to carry out each reaction in the following sequence?arrow_forward
- The 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_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 cyclohexanone and propenal Draw the structure of the product of the enamine formed between cyclohexanone and dimethylamine. - Michael addition to an α,β-unsaturated carbonyl compound, and - hydrolysis of the enamine in dilute acid to regenerate the ketone.arrow_forwardChoose the best sequence of reagents to synthesize the indicated compound.arrow_forward
- β-Vetivone is isolated from vetiver, a perennial grass that yields a variety ofcompounds used in traditional eastern medicine, pest control, and fragrance. In one synthesis, ketone A is converted to β-vetivone by a two-step process: Michael reaction, followed by intramolecular aldol reaction. (a) What Michael acceptor is needed for the conjugate addition? (b) Draw a stepwise mechanism for the aldol reaction, which forms the six-membered ring.arrow_forwardDevise concise syntheses for the following transformations. Clearly show the reagent and product foreach step.arrow_forwardPropose a synthesis for each product.arrow_forward
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