In crossed aldol condensation，in order to avoid unwanted product mixture，the compound without alpha hydrogen like benzaldehyde can be a good choice. Why？？？does it means that two enolate will produce unwanted product mixture？1. what is unwanted product mixture ？2. and what is wanted product？ HolateH3C-CH3HateHOH-utanal)nzaldehydeHHHH-C-CH3C-C-HH-HOHis usually exothermic, driving the condensation to completion. The base-catalyzed dehydration of 3-hydroxybutanal is shown in Equation 2.HC-CH3HHHO HC-C-HHenolate ionOHOH -C-CH3HOHH O HH-C-CH3C-C-H + TOHHHaldol (3-hydroxybutanal)A crossed aldol condensation is an aldol condensation in whichone aldehyde or ketone adds to the carbonyl group of a differentcompound. The compounds used in a crossed aldol condensation mustbe carefully selected to avoid unwanted product mixtures. Crossed aldolcondensations are most effective if only one of the reactants can form anenolate ion and the other reactant is particularly electrophilic towardenolates. Benzaldehyde is an excellent reagent for crossed aldols because ithas no a-hydrogens, so it cannot form an enolate. The base-catalyzedcondensation of acetaldehyde with benzaldehyde is shown in Equation 3.HCH3HHdehydratedOHH-C-(Eq. 1)C-C-HHaldol+ OH(Eq. 2)+ OH

Aldol condensation is a reaction that involves the formation of a new carbon-carbon bond through the…

In crossed aldol condensation，in order to avoid unwanted product mixture，the compound without alpha hydrogen like benzaldehyde can be a good choice. Why？？？does it means that two enolate will produce unwanted product mixture？ 1. what is unwanted product mixture ？ 2. and what is wanted product

In crossed aldol condensation，in order to avoid unwanted product mixture，the compound without alpha hydrogen like benzaldehyde can be a good choice. Why？？？does it means that two enolate will produce unwanted product mixture？ 1. what is unwanted product mixture ？ 2. and what is wanted product

Organic Chemistry

8th Edition

ISBN:9781305580350

Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Publisher:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. Foote

Chapter16: Aldehydes And Ketones

Section: Chapter Questions

Problem 16.47P: The base-promoted rearrangement of an -haloketone to a carboxylic acid, known as the Favorskii...

See similar textbooks

Similar questions

When a primary alcohol is treated with p-toluenesulfonyl chloride at room temperature in the presence of an organic base such as pyridine, a tosylate is formed. When the same reaction is carried out at higher temperature, an alkyl chloride is often formed. Explain.
Which of these would be best to convert pentanal into 2-hexanol? O CH3MgBr then H3O+ NaBH4 CH3OH, H+ CH3CI, AICI3 O (CH3)2CuLi then H3O+
Identify the following as hemiacetals or acetals. 0-CH2- CH- CH3 CH3-C-H Ó-CH2- CH2- CH3 hemiacetal acetal Submit Previous Answers Correct Part F Give the names of the carbonyl compounds and alcohols used in its synthesis. Give your answers in the order: carbonyl compound, alcohol. ethanal,propanol Submit Previous Answers Request Answer X Incorrect; Try Again; 5 attempts remaining
What is an appropriate stepwise synthesis for the following synthesis that uses 1-propanol as the only source of carbon and any other reagents as needed? CH3CH2CH2OH CH3CH2CH2CHCOCH2CH2CH3 CH3 O A. 1-propanol reacts with PCC/CH2Cl2 to yield an intermediate that reacts with LDA to yield intermediate X, which has a resonance form Y. 1-propanol also reacts with PCl3 to yield an intermediate Z that reacts with intermediate X, which undergoes the following series of reactions to yield the product: 1. Na2Cr2O7/H2SO4/H2O; 2. Excess CH3CH2CH2OH/H2SO4. OB. 1-propanol reacts with PCC/CH2Cl2, then the product reacts with LDA to produce intermediate X, which has resonance forms. 1-propanol reacts with PCl3, then the product reacts with intermediate X to yield intermediate Y. Intermediate Y reacts with NaBH4/CH3OH to yield the product. SUPPORT OC. 1-propanol reacts with PCl3 to yield intermediate X. 1-propanol also undergoes the following reaction sequence: 1. Na2Cr2O7/H2SO4/H2O; 2. excess…
Provide the reagents necessary to carry out the following conversion: 4-methyl-cyclohexanol -------> 4-methyl- cyclohexanone O KMNO4/NAOH/H20 peroxyacetic acid O Br2, CCl, O NazCr207/H2SO2/H2O O OsO4
The compound shown below is the cyclic hemiacetal of НаС ОН O. CH2CH3 O 6-hydroxyheptanal. 5-hydroxyheptanal. 5-hydroxy-2-heptanone 6-hydroxy-3-heptanone.
Treatment of a carboxylic acid with trifluoraacetic anhydride leads to an unsymmetrical anhydride that rapidly reacts with an alcohol to give an ester. Q5. F3C CF3 trifluoroacetic anhydride CH;CH,OH H3C + CF;CO,H HO, H3C" CF3 H3C OCH2CH3 Unsymmetrical anhydride 1 Ethyl ester 2 (a) Propose a mechanism, using curved arrows, for the formation of the unsymmetrical anhydride 1. (b) Propose a mechanism, using curved arrows, for the formation of the ethyl ester 2. (c) Why is the unsymmetrical anhydride unusually reactive?
Starting with 1-pentanol identify any necessary reagents needed to make 1,2-epoxypentane
Would you expect 1-methyl-1-cyclohexanol to dehydrate at a faster or slower rate than cyclohexanol? Explain your answer by referring to the mechanism of the reaction. Explain step by step in details.
6. Write the mechanism for the base-catalyzed keto-enol interconversion shown below. H₂C CH3 OH CH2=CH—C—CH3 H₂C OH CH3 7. Write a mechanism for the following reaction: + CH3–CH2CH,—C-H OH A CH₂CH3
b) Clopirac has been used as a non-steroidal anti-inflammatory (NSAID) drug. The synthesis of clopirac involves reaction of 4-chloroaniline with hexan-2,5-dione in an initial step. Identify the named reaction that is taking place in this initial step and propose a mechanism for it. -NH₂ + $- Clopirac CO₂H
Among the tertiary alcohols shown below, which one cannot be synthesized by reacting an appropriate Grignard reagent with an ester? CH2CH3 H3C-C-OH CH3 CH3 H3C-C-OH CH3 CH2CH3 H3C-C-OH CH2CH3 CH,CH3 H3C-C-OH CH(CH3)2 CH(CH3)2 H3C-C-OH CH(CH3)2