Concept explainers
(a)
Interpretation: Nabumetone from ethyl acetoacetate is to be synthesized.
Concept introduction: The
(b)
Interpretation: The alkyl halide and ketone needed to prepare nabumetone are to be predicted.
Concept introduction: Carbonyl compounds on treatment with a strong base result in alkylation. The reaction is carried out in two steps: first is the removal of proton by base to generate enolate ion. The second step is the attack of nucleophillic enloate on the alkyl halide, displacing the halide and formation of alkylated product takes place via
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- Illustrate the Separation of cyclohexanamine and cyclohexanol by an extraction procedure ?arrow_forwardThe reaction of a nitrile with an alcohol in the presence of a strong acid forms an N-substituted amide. This reaction, known as the Ritter reaction, doesnot work with primary alcohols. a. Why does the Ritter reaction not work with primary alcohols? b. Provide an explanation for why an amide is less susceptible to nucleophilic attack than its corresponding ester.arrow_forwardOne synthesis of the cholesterol-lowering drug atorvastatin involves the construction of the pyrrole by reaction of diketone X with amine Y. Draw a stepwise mechanism for this reaction.arrow_forward
- Why is it not advisable to use aqueous hydrochloric acid in a Grignard reaction of a ketone? A) The Grignard reagent will react with the acid and cannot react with the ketone. B) The ketone will be protonated and will become unreactive. C) The ketone will form an unreactive enol. D) The Grignard reagent won't dissolve in aqueous solutionsarrow_forwarda) Put these three common types of carbonyl compound in order of decreasing reactivity ester amide acid chloride b) For the least reactive, show the interconversion to its other resonance form: How does this electron delocalisation make it stable? c) For the most reactive, draw the mechanism of its undergoing hydrolysis (reaction with H2O): Why makes this type of carbonyl so reactive to nucleophiles?arrow_forwardwhy sulfanilamide is less acidic than sulfathiazole (B), whereas sulfanilylsulfanilamide is more acidic than sulfathiazole? does it relate to hard and soft nucleophiles?arrow_forward
- Design a stepwise synthesis to convert cyclopentanone and 4- bromobutanal to hydroxy aldehyde A.arrow_forwardLinalool and lavandulol are two of the major components of lavender oil. (a) What organolithium reagent and carbonyl compound can be used to make each alcohol? (b) How might lavandulol be formed by reduction of a carbonyl compound? (c) Why can't linalool be prepared by a similar pathway?arrow_forwardExplain nucleophilic addition to the aldehyde to form analcohol ?arrow_forward
- Why is an alkylamine more basic than ammononia?arrow_forwardDraw a stepwise mechanism for the sulfonation of an alkyl benzene such as A to form a substituted benzenesulfonic acid B. Treatment of B with base forms a sodium salt C that can be used as a synthetic detergent to clean away dirtarrow_forwardExplain why the acetylation requires one mole of acetic anhydride per mole of aniline, though acetic anhydride contains two acetyl groups. How is the by-product containing the second acetyl group removed from acetanilide?arrow_forward
- Organic Chemistry: A Guided InquiryChemistryISBN:9780618974122Author:Andrei StraumanisPublisher:Cengage Learning