(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 MASTERINGCHEM ACCESS
- Draw the product formed when each dicarbonyl compound undergoes anintramolecular aldol reaction followed by dehydration, when possible.arrow_forwardSelect the di-carbonyl compound that would efficiently form the structure shown via an intramolecular Aldol reaction. A. or B. •oo •ay E. og F. olarrow_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_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 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_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_forward
- Draw 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_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_forwardDraw the major product of this aldol addition reaction. Ignore inorganic byproducts. 1. LDA 2. C6H11CH2CHO 3. Neutralizing work-up Drawing Qarrow_forward
- In 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_forwardWhich is a reasonable intermediate in an aldol reaction of propanal? H. H. Ноarrow_forward2. When the following pair of reactants are combined in the presence of a basic catalyst, a number of aldol addition products are possible (since both of the reactants possess an acidic alpha proton). a. b. C. CH3 + H₂C H NaOH/H₂O Draw the structures for the two possible enolate ions. Draw the structures for all possible aldol addition products (also show the enolate ion and electrophilic carbonyl compound responsible for each product). For each of the aldol addition products predicted in part b, draw the structures for all of the corresponding aldol condensation products after loss of water (if E/Z isomers are possible, show both isomers)arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning