Many of the condensations we have studied are reversible. Reverse reactions often give the prefixretro-, from Latin meaning "backwards." Propose mechanisms to explain the following reactions.CH, HCH,OHCH,(retro-aldólica y condensación posterior)CH,(d)а-OH"OCHCH₂OHCOOCH3(retro-aldólica y de Claisen cruzada)

Answered: Many of the condensations we have…

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter20: Carboxylic Acids And Nitriles

Section20.SE: Something Extra

Problem 57AP: A chemist in need of 2,2-dimethylpentanoic acid decided to synthesize some by reaction of...

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The intramolecular Aldol condensation of 2,6-heptancdione with base may produces two possible Bhydroxyl ketones as shown in the following reaction pathway. CH, (1) OH CH, (A) 3-Methyl-2-cyclohexenone .CH, CH, (2) OH - CH3 2,6-Heptanedione (B) Methyl(2-methyl-1-cyclobutenyl)ketone Write detailed mechanisms for both the reactions (1) and (2).
Propose a mechanism for this isomerization.
The formation of Br2 from NBS first involves the reaction of NBS with HBr to form an iminol intermediate and molecular bromine. The intermediate then undergoes acid-catalyzed tautomerism to form succinimide, the byproduct of the reaction. Propose a curved-arrow mechanism for the conversion of NBS into succinimide that also accounts for the formation of Br2.
A chemist in need of 2,2-dimethylpentanoic acid decided to synthesize some by reaction of 2-chloro-2-methylpentane with NaCN, followed by hydrolysis of the product. After the reaction sequence was carried out, however, none of the desired product could be found. What do you suppose went wrong?
Solvolysis of the following bicyclic compound in acetic acid gives a mixture of products, two of which are shown. The leaving group is the anion of a sulfonic acid, ArSO3H. A sulfonic acid is a strong acid, and its anion, ArSO3, is a weak base and a good leaving group. Propose a mechanism for this reaction.
Complete the reaction scheme below. Show all reagents and intermediates. No reaction is a possible answer. 1) CH3CH2M9B CH3OH H+ (ехcess) но 2) H30*, H2O B A OCH3
Treatment of pentanedioic (glutaric) anhydride with ammonia at elevated temperature leads to a compound of molecular formula C5H7NO2. What is the structure of this product? [Hint: You need to think about the reactivity not only of acid anhydrides but also of amides and carboxylic acids]. Please show mechanism.
1. Propose a mechanism for the following transformation: R COOH (1) H₂C-O, (C₂H₂)₂NH (2) H₂O, acetate buffer R CH₂
Propose a mechanism for this reaction. CI + Cl2 + HCI CH3COOH (racemic)
When a methyl ester is hydrolyzed under acidic conditions in H,180, the 180 isotope ends up in the carboxylic acid. When a tert-butyl ester is hydrolyzed under the same conditions, the labeled oxygen ends up in the alcohol product. (a) Propose mechanisms to account for these observations. (b) Explain why each ester undergoes the respective mechanism. CH3 + Но-СНЗ 18 + H180 H ОН
The intramolecular aldol reaction of 6-oxoheptanal [CH3CO(CH2)4CHO] can yield threecyclic D,E-unsaturated ketones. Give the threeproducts and suggest a mechanism for formingone of the products.
The widely used anticoagulant warfarin (see "Chemical Connections: From Moldy Clover to a Blood Thinner" in Chapter 18) is synthesized from 4-hydroxycoumarin, benzaldehyde, and acetone as shown in this retrosynthesis. Show how warfarin is synthesized from these reagents. OH OH Acetone + Warfarin 4Нydroxy- (a synthetic anticoagulant; racemic) coumarin Benzaldehyde

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