Mixed Aldols With Acidic Carbonyl Compounds ■ Ethyl acetoacetate is completely converted into its enolate ion under less basic conditions than monocarbonyl partners ■Aldol condensations with ethyl acetoacetate occur preferentially to give the mixed product Cyclohexanone (acceptor) ©2007 Thomson Higher Education 0 || 0 || CH3CCH₂COCH₂CH3 Ethyl acetoacetate (donor) Na+ -OEt Ethanol H3C- Jama CO,CH,CH3 + H2O 80% 17

Mixed Aldols With Acidic Carbonyl Compounds ■ Ethyl acetoacetate is completely converted into its enolate ion under less basic conditions than monocarbonyl partners ■Aldol condensations with ethyl acetoacetate occur preferentially to give the mixed product Cyclohexanone (acceptor) ©2007 Thomson Higher Education 0 || 0 || CH3CCH₂COCH₂CH3 Ethyl acetoacetate (donor) Na+ -OEt Ethanol H3C- Jama CO,CH,CH3 + H2O 80% 17

Organic Chemistry

9th Edition

ISBN:9781305080485

Author:John E. McMurry

Publisher:John E. McMurry

Chapter23: Carbonyl Condensation Reactions

Section23.SE: Something Extra

Problem 56AP

See similar textbooks

Similar questions

Match the questions with the correct descriptions below: Sn2, E2 E1cb Sn1, E1 (anti) E2, E1cb Sn1, E1 2 steps poor leaving group 2 carbons removed from a carbonyl group carbanion intermediate 3°>allylic, benzylic>2°>1°>CH₃ carbocation intermediate Ist order reaction (r=k[RX]) H-X anti no intermediate 2nd order reaction (r=k[RX][Nu]) polar aprotic solvent
Please help me with the mechanism for what is described below: 1. Draw a mechanism for the reaction dscribed: The Wittig Reaction Reactants: NaOH, (4-picolyl)triphenylphosphonium chloride, dichloromethane, 4-pyridinecarboxaldehyde (also known as isonicotinaldehyde), HCl, Na2CO3 Final product: trans-4,4'-bpe
The enolate derived from diethyl malonate reacts with a variety ofelectrophiles (not just alkyl halides) to form new carbon–carbon bonds.With this in mind, draw the products formed when Na+ −CH(CO2Et)2reacts with each electrophile, followed by treatment with H2O.
Draw reaction mechanisms with all reactants, arrows, intermediates, and products. Your mechanism must account for all the products if more than one product is formed. 4-methycyclohexanol with phosphoric acid H3PO4 to for 1-methycyclohexene, 3- methylcyclohexene and 4-methycyclohexene
Consider the series of the trans effect: CO, CN-, C2H4 > PR3, H-, CH3- > C6H5- > NO2-, SCN-, I- > Br- >Cl- > py > NH3 > H20 What would be the major product of the following reaction? Select one:
Draw the mechanism ffrom benzaldehyde to this using: i)NaBH4 ii)TsCl, py iii)NaCN iiii)H+, H2O
The iodination of acetovanillone (1-(4-hydroxy-3-methoxyphenyl)ethan-1-one) occurs in the following reaction: C9H10O3 + NaI + NaOCl --> C9H10O3I + NaCl Draw the complete reaction mechanism of acetovanillone including curved arrows.
Rank the nucleophiles in each group in order of increasing nucleophilicity. a.−OH, −NH2, H2O b.−OH, Br−, F− (polar aprotic solvent) c.H2O, −OH, CH3CO2−
For problem 8.17, all of the reactions will be SN2. For each reaction, identify and evaluate each nucleophile (strong? weak? Strong or weak as a base?) Also, evaluate each solvent as polar protic or polar aprotic. I recommend drawing the structure of each solvent. (d) Sodium cyanide in dimethyl sulfoxide (e) Sodium azide in aqueous ethanol (f) Sodium hydrogen sulfide in ethanol
Triethyloxonium tetrafluoroborate, (CH3CH2)3O+ BF4 −, is a solid with melting point 91–92 °C. Show how this reagent can transfer an ethyl group to a nucleophile (Nuc:−) in an SN2 reaction. What is the leaving group? Why might this reagent be preferred to using an ethyl halide?
Show the organic product formed when methyl propanoate is reacted with lithium diisopropyl amide, then methyl butanoate is slowly added to the mixture. The mixture is neutralized with aqueous acid to obtain a neutral product. Show the steps in the mechanism as reactant is converted to final product. show appropriate arrow pushing and any charges, and draw a box around the final product.
Which condition or sequence is ideal for converting ethyne into the epoxide shown below? A. 1. D2 (1 equivalent)/Pd-C 2. H3CC(O)OOH B. 1. D2/Lindlar 2. H3CC(O)OOH C. 1. H3CC(O)OOH 2. D2/ Pd-C D. 1. Na/ND3 2. H3CC(O)OOH