(a)
Interpretation:
The validation of the fact that the given ester cannot be synthesized by malonic ester synthesis is to be stated with an explanation.
Concept introduction:
Deprotonation of malonic ester giveenolate ion. This enolate ion is alkylated by an unhindered
(b)
Interpretation:
The acid-base reaction between LDA and the given ester is to be stated and the direction of equilibrium is to be predicted.
Concept introduction:
LDA (Lithium Di-isopropyl Amide) is a strong base with a molecular formula,
(c)
Interpretation:
The method of preparation of given compound using malonic ester synthesis is to be stated.
Concept introduction:
Deprotonation of malonic ester give enolate ion. This enolate ion is alkylated by an unhindered alkyl halide, tosylates or any other electrophilic species through displacement to give alkylated diethyl malonate. It will undergo hydrolysis to give substituted acetic acid.
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Chapter 22 Solutions
EP ORGANIC CHEMISTRY -MOD.MASTERING 18W
- An alternative procedure for preparing the amine of Step 3 is reductive amination of the corresponding ketone. What is reductive amination? Why might this two-step route for formation of the amine be preferred over the one-step reductive amination?arrow_forward10.) Would the base sodium phenoxide be a good choice for deprotonation of ethyl acetoacetate (pKa = 11)? Explain your answer fully. b) Why is ethyl acetoacetate so acidic compared to the average ketone or ester, which have pKa values in the lower 20s?arrow_forwardHow does the pKe of the conjugate acid of benzylamine (C3H5CH,NH2) compare to the pK,'s of the conjugate acids of cyclohexanamine (10.7) and aniline (4.6)? Explain your choice.arrow_forward
- The reaction between propanoic acid and benzylalcohol in an acidic medium. show the product by writing the reaction together with its mechanism.arrow_forwardGive the shortest route to produce the desired products 1. cyclobutanoic acid to ethyl-cyclobutyl ketone 2. 2-butanone to pentatonic acid 3. propane to butanaminearrow_forwardSpasmolytol, as its name suggests, is an antispasmodic. Given this retrosynthetic analysis, propose a synthesis for spasmolytol from salicylic acid, ethylene oxide, and diethylamine. Br. NEto OH OCH3 ОН Br Spasmolytol Salicyclic acidarrow_forward
- ANAL 728: Identifying an Unknown Aldehyde or Ketone 4. In the procedure for preparing semicarbazone derivatives, what is the pur- pose of adding sodium acetate to semicarbazide hydrochloride? TAE MOIT EMAN SHoS 10 shysshlA ruoolrU nn gniytiinshl18STJAMA InsmngizaA yiolsTodsl-911arrow_forwardTOPIC: Ester Synthesis via Nucleophilic Acyl Substitution Write the chemical equation involved in the reaction between the excess acid and NaHCO3 and briefly explain why NaHCO3 is preferred over NaOH for the neutralization of excess acid.arrow_forward5. Write a flow chart to show how you could separate the following pairs of compounds by using acid-base extraction. a) fluorenone and p-bromobenzoic acid do b) p-nitrophenol and p-bromobenzoic acid HO NO₂ c) p-aminobenzoic acid and p-bromobenzoic acid H₂N Br OH يوم vol ob OH Br OH & OHarrow_forward
- Which of the following compounds would have the lowest K, value? 3-Nitrobenzoic Acid O 3-Methylbenzoic Acid O 3-Aminobenzoic Acid Question 8 Which of the following compounds would have the lowest pK, value?arrow_forwarddraw the following reactions and label it properly 1. Esterification of benzoic acid with n-propyl alcohol and concentrated H2SO4. 2. Esterification of salicylic acid with n-propyl alcohol and concentrated H2SO4. 3. Esterification of acetic acid with n-propyl alcohol and concentrated H2SO4. 4.Reaction with neutral FeCl3 with acetic acid 5. Reaction with neutral FeCl3 with tartaric acidarrow_forwardShow how the amino acid alanine can be synthesized from propanoic acid. a. Show how the amino acid glycine can be synthesized from phthalimide and diethyl 2-bromomalonatearrow_forward
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