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Concept explainers
Interpretation:
A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.
Concept introduction:
The steps involved in the conversion required are i) Attack of the hydroxide ion on α, β-unsaturated
To give:
A mechanism for the base catalyzed isomerisation of the minor product formed in the intramolecular aldo cyclization of 2, 5-heptanedione into the major product upon treatment with aqueous NaOH is to be proposed.
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Chapter 23 Solutions
Organic Chemistry
- Acid-catalyzed hydrolysis of the following epoxide gives a trans diol. Of the two possible trans diols, only one is formed. How do you account for this stereoselectivity?arrow_forwardPropose a mechanism for this isomerization.arrow_forwardThe Favorskii reaction involves treatment of an -bromo ketone with base to yield a ring-contracted product. For example, reaction of 2-bromocyclohexanone with aqueous NaOH yields cyclopentanecarboxylic acid. Propose a mechanism.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 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_forwardPropose a mechanism for the aldol reaction below 2 H3C H OH-, H2O se H3C Harrow_forwardShow a reasonable mechanism for the following reaction (Hint: Michael addition followed by intramolecular aldol condensation) ☆ NaOEt, EtOH Aarrow_forward
- 2. Propose a synthesis of the following molecule using an aldol reaction. OH 3. Imines can undergo reduction reactions with sodium borohydride to produce amines by a similar mechanism to how aldehydes and ketones react to produce alcohols. With thatin mind, propose a mechanism for the following reaction and give the structure of theamine product. N 1. NABH4 2. H30* iminearrow_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_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 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_forward
- 5. Propose a mechanism for the base-catalyzed hydrolysis of the nitrile. H₂O NaOH CEN 6. Propose a mechanism for aldol reaction. HiM Н н NaOH H₂Oarrow_forwardPlease give the appropriate reagents to complete the following synthesis. H ? hy=3arrow_forwardAcetophenone and formaldehyde undergo a mixed aldol addition. Which compound will react as CH - acidic and carbonyl component respectively, and why? Show the structures of the favoured aldol addition and aldol condensation products.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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