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Interpretation:
A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl
Concept introduction:
The steps involved in the formation of the iminium ion are i) Protonation of the
The reaction between iminium ion intermediate and cyclohexanone takes place through the following steps i) Reaction between the enol form of the cyclohexanone and iminium ion ii) Deprotonation of the intermediate.
To propose:
A mechanism for the first step in the Mannich reaction shown, a reaction between acetaldehyde and dimethyl amine, to yield an iminium ion intermediate along with water. To show the structure of the iminium ion intermediate.
Further to propose a mechanism for the second step involving the reaction between iminium ion intermediate and cyclohexanone.
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Chapter 23 Solutions
Organic Chemistry
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- Early organic chemists used the Hofmann elimination reaction as the last step of a process known as a Hofmann degradation—a method used to identify amines. In a Hofmann degradation, an amine is methylated with excess methyl iodide in a basic solution, treated with silver oxide to convert the quaternary ammonium iodide to a quaternary ammonium hydroxide, and then heated to allow it to undergo a Hofmann elimination. Once the alkene product is identified, working backward gives the structure of the amine. Identify the amine in each of the following cases: a. 4-Methyl-2-pentene is obtained from the Hofmann degradation of a primary amine. b. 3-Methyl-1-butene is obtained from the Hofmann degradation of a primary amine. c. 2-Methyl-1-3-butadiene is obtained from two successive Hofmann degradations of a secondary amine.arrow_forwardWhen ethyl bromide is added to potassium tert-butoxide, the product is ethyl tert-butyl ether.(a) What happens to the reaction rate if the concentration of ethyl bromide is doubled?arrow_forwardWhen tert-butyl bromide is heated with an equal amount of ethanol in an inert solvent, one of the products is ethyl tert-butyl ether. (a) What happens to the reaction rate if the concentration of ethanol is doubled?arrow_forward
- Draw a structural formula for the product formed by treating butanal with each reagent. (a) LiA1H4LiA1H4 followed by H2OH2O (b) NaBH4NaBH4 in CH3OH/H2O (c) H2/Pt (d) Ag(NH3)2+in NH3/H2O (e) H2CrO4, heat (f) HOCH2CH2OH,HClarrow_forward(c) Arrange the following compounds in order of increasing acidity, and explain the reasons for your choice of order: phenol, cyclohexanol, 2-fluorocyclohexanol, 2-fluorophenol.arrow_forwardProvide a two step method to distinguish between the following compounds. (Propanal, butanal, butanone, propanone). Explain your choice of reagents and your expected results.arrow_forward
- Organic ChemistryChemistryISBN:9781305580350Author:William H. Brown, Brent L. Iverson, Eric Anslyn, Christopher S. FootePublisher:Cengage Learning
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