(a)
Interpretation:
The major product of the given base-catalyzed aldol condensation with dehydration is to be predicted.
Concept introduction:
When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol
(b)
Interpretation:
The major product of the given base-catalyzed aldol condensation with dehydration is to be predicted.
Concept introduction:
When a basic or acidic mixture of an aldol product is heated, dehydration of an alcohol functional group takes place. The product formed is a conjugated
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Chapter 22 Solutions
Organic Chemistry (9th Edition)
- 4. Give the structures of the aldol products that form when each of the following compounds or mixtures is treated with NAOH. a) Butanal b) Cyclopentanone c) Acetophenone d)-Chlorobenzaldehyde and 2,2-dimethylcyclohexanonearrow_forwardThe Stork reaction is a condensation reaction between an enamine donor and an a,ẞ-unsaturated carbonyl acceptor. The overall reaction consists of a three-step sequence of 1. formation of an enamine from a ketone. 2. Michael addition to an α,ß-unsaturated carbonyl compound, and 3. 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. ચર્ચ F Correct HC, CH3 ChemDoodle 2 Draw the structure of the Michael addition product. ChemDoodle Jn (F 106 Correctarrow_forwardDraw the major product of the aldol condensation reaction between two equivalents of this aldehyde with the conditions provided. Ignore inorganic byproducts. 1. NaOH, heat H 2. Neutralizing work-up O 4arrow_forward
- Which statement describes why aldol reactions with ketones are low yielding? A.Ketones do not have acidic protons. B.Ketones are too electron poor at the carbonyl carbon. C.Ketones can attack other ketones well but perform poorly in self-condensations. D.The product of a ketone addition to a ketone has considerable steric strain.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_forwardDraw the major product of the aldol condensation reaction between two of equivalents of this aldehyde with the conditions provided. Ignore inorganic byproducts. 1. H3O+, heat 2. Neutralizing work-up Drawing H Qarrow_forward
- Draw the major product of this aldol addition reaction. Ignore inorganic byproducts. 1. LDA 2. C6H11CH2CHO 3. Neutralizing work-up Drawing Qarrow_forwardDoes it matter whether acetone is added first to the eq. NaOH solution then the benzaldehyde, or if the benzaldehyde is added first to the aq. NaOH solution, then the acetone in an aldol synthesis of dibenzalacetonearrow_forwardIn a mixed aldol addition reaction between these two molecules, which one forms the enolate ion? لمسلم -CH3 acetophenone -H benzaldehyde acetophenone benzaldehyde both of them can form an enolate. neither of them can form an enolate.arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning