Concept explainers
Interpretation:
The major product of the given reaction sequenceis to be determined.
Concept Introduction:
Reaction of an aldehyde or a ketone with a secondary
If the aldehyde or ketone is unsymmetrical, then a mixture of two enamines is obtained.
In this mixture of enamines, the one with the less substituted double bond predominates.
Enamines are nucleophilic and react with electrophiles forming a new carbon-carbon bond. Further, hydrolysis produces a derivative of the original aldehyde or ketone such that the substituent is attached to the alpha position.
Primary
Want to see the full answer?
Check out a sample textbook solutionChapter 22 Solutions
Organic Chemistry - Standalone book
- How can ferric chloride reagent be use to test for basicity of amines? Provide the chemical equation for this reaction.arrow_forwardSalsalate, which is an ester formed by the reaction of two molecules of salicylic acid, is another salicylate used as an aspirin alternative for those who are hypersensitive to aspirin. Draw the structures of salicylic acid and salsalate.arrow_forwardDescribe the product formed as a result of the reaction between benzylamine and ethylacrylate by writing the mechanism of the reaction.arrow_forward
- Give a chemical test to distinguish between each of the following pairs of compounds :(i) Ethylamine and Aniline(ii) Aniline and Benzylaminearrow_forward2. Write the equation for the reaction of acetanilide with molecular bromine (for the organic compounds, draw the full structures, not condensed formulae).arrow_forwardQ4:- Draw structures, give names, and classify as primary, secondary, or tertiary amine : the eight isomeric amines of formula CaHi.N Q5:- Give structures and names of the principal organic reactants and products of the following reactions. a- conversion of Carboxylic Acids into Esters b- Hydrolysis of nitrites. c- Hofmann degradation of amides Q6:- Arrange the compounds of each set in order of basicity ? Explain your choice. ethylamine, 2-aminoethanol, 3-amino-l-propanolarrow_forward
- N-Methylpyrrolidine has a boiling point of 81 °C, and piperidine has a boiling point of 106 °C. Tetrahydropyran has a boiling point of 88 °C, and cyclopentanone has a boiling point of 141 °C. These two isomershave a boiling point difference of 53 °C. Explain why the two oxygen-containing isomers have a much larger boilingpoint difference than the two amine isomersarrow_forwardAmines with more than 6 carbons are soluble in: a) aqueous HCI b) aqueous NaHCO3 d) water c) aqueous NaOH Which of the following would give a positive iodoform test? acetone a) benzophenone c) 3-pentanone d) cyclopentanone meth "Saponification" as the term is used in organic chemistry means: a) acidic hydrolysis of an ester b) basic hydrolysis of an ester c) acidic hydrolysis of an amide d) basic hydrolysis of an amide 3. ( Propylamine can be synthesized by the LiAlH4 reduction of: a) CH3CH2CECH b) CH3CH=NH d)) CH3CH2CEN c) CH3CH2NO2arrow_forwardAnilines can be converted into diazonium salts by reaction with nitrous acid. Diazonium salts react with phenols to form azo dyes. Sketch the aniline derivative and phenol reactant that can combine to produce the azo dye shown.arrow_forward
- Ethylamine is soluble in water, whereas aniline is almost insoluble, why?arrow_forwardWhy is methylamine more basic than aniline?arrow_forwardWhen trans-2-chloro-1-cyclohexanol is treated with a base, cyclohexene oxide is the product. However, when cis-2-chloro-1-cyclohexanol is treated with a base, the product is cyclohexanone A.Write the equation for the reaction between trans-2-chloro-1-cyclohexanol and the base to yield the cyclohexene oxide B.Why doesn’t the cis isomer yield the oxide? C.Write the mechanism for each of the two reactions.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage LearningChemistry: The Molecular ScienceChemistryISBN:9781285199047Author:John W. Moore, Conrad L. StanitskiPublisher:Cengage LearningChemistry for Today: General, Organic, and Bioche...ChemistryISBN:9781305960060Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. HansenPublisher:Cengage Learning
- Chemistry: Matter and ChangeChemistryISBN:9780078746376Author:Dinah Zike, Laurel Dingrando, Nicholas Hainen, Cheryl WistromPublisher:Glencoe/McGraw-Hill School Pub Co