The intramolecular Aldol condensation of 2,6-heptanedione with basc may produces two possible B-hydroxyl ketones as shown in the following reaction pathway. CH, (1) OH CH, (A) 3-Methyl-2-cyclohexenone .CH, CH, (2) OH CH, 2,6-Heptanedione (B) Methyl(2-methyl-1-cyclobutenyl)ketone Write detailed mechanisms for both the reactions (1) and (2).

The intramolecular Aldol condensation of 2,6-heptanedione with basc may produces two possible B-hydroxyl ketones as shown in the following reaction pathway. CH, (1) OH CH, (A) 3-Methyl-2-cyclohexenone .CH, CH, (2) OH CH, 2,6-Heptanedione (B) Methyl(2-methyl-1-cyclobutenyl)ketone Write detailed mechanisms for both the reactions (1) and (2).

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.3: Dehydration Of Aldol Products: Synthesis Of Enones

Problem 4P

See similar textbooks

Similar questions

Q1/A) Arrange the following sets of compounds in order of: 1) Increasing acidity H₂C CH₂ H₂C OCH₂CH₂ OCH₂CH3 Ph, изза паззакон показзаки здають 2) Increasing yield in cross Aldol condensation p-methyl benzaldehyde, p-methoxy benzaldehyde, benzaldehyde, p-nitro benzaldehyde 3) Stability of carbanion ion O 11 유 CH3-CN, CH3-C-OCH3. CH3-C-CH3, CH3NOz
Give the structures of the aldol products that form when each of the following compounds or mixtures is treated with NaOH. The top three compounds are aldol dimerizations and require 2 moles of the reactant listed, while the two compounds on the bottom row are being used in a mixed aldol reaction. Butanal, Cyclopentanone, and Acetophenone (PhCOCH3) p-chlorobenzaldehyde and 2,2-dimethylcyclohexanone
• Using aldol or crossed aldol condensation, suggest a synthesis of the following compounds: a b مليمت H3C H3C CH3 H3C ge H Saved
Predict the major products of the following base-catalyzed aldol condensations withdehydration.(a) benzophenone (PhCOPh) + propionaldehyde(b) 2,2@dimethylpropanal + acetophenone
In theory, the intramolecular aldol reaction of 6-oxoheptanal could yield the three compounds shown. It turns out, though, that 1-acetylcyclopentene is by far the major product. Why are the other two compounds formed in only minor amounts? Draw a stepwise mechanism to show how all three products are formed.
Q/ Give the product for the following reactions: OH (1) Acetone + acetaldehyde OH (2)2 Acetone ? Q/ Give the mechanism of reactions (1) and (2). Q/ Give the mechanism of aldol condensation under the influence of dilute acid.
Which of the following compounds would you expect to undergo aldol self-condensation? Show the product of each successful reaction. (a) Trimethyl acetaldehyde (d) 3-Pentanone(b ) Cyclobutanone (e) Decanal(c) Benzophenone (diphenyl ketone) (f) 3-Phenyl-2-propenal
Draw the product formed (after dehydration) in the crossed aldol condensation of phenylacetaldehyde (C6H5CH2CHO) with CH2(CO2Et)2 in the presence of sodium hydroxide.
The following reaction involves two sequential Heck reactions. Draw structural formu- las for each organopalladium intermediate formed in the sequence and show how the final product is formed. Note from the molecular formula given under each structural formula that this conversion corresponds to a loss of H and I from the starting material. Acetonitrile, CH,CN, is the solvent. 1% mol Pd(OAc), 4% mol Ph,P CH,CN C4H171 C4H16
3‑Methylbutanal undergoes an aldol reaction to form 3‑hydroxy‑2‑isopropyl‑5‑methylhexanal. Complete the mechanism for the reaction by adding missing atoms, bonds, charges, nonbonding electrons, and curved arrows
What reactant can be used to make this compound by an intramolecular aldol reaction? (A) (B) (C) (D) لسل H
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-keto ester and the α,β-unsaturated ketone acceptor that were combined in a Robinson annulation to give the following product: Draw the β-keto ester as an ethyl ester,