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An acetoacetic ester synthesis of a ketone proceeds by alkylation of the enolate of the acetoacetic ester followed by ester hydrolysis and decarboxylation of the
-ketoacid. Which of the following methyl ketones is difficult to prepare by this method?
  • a)
  • b)
  • c)
  • d)
Correct answer is option 'D'. Can you explain this answer?
Verified Answer
An acetoacetic ester synthesis of a ketone proceeds by alkylation of t...
The alkylation of the enolate is an
reaction, and sterically hindered alkyl groups are difficult to introduce. However, even dialkylation is possible with reactive alkylating agents, as in (d).
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Consider a solution of CH3COONH4 which is a salt of weak acid weak base. Theequilibrium involved in the solutions are :If we add these three reactions, then the net reaction isBoth CH3C00- and NH4 get hydrolysed independently and their hydrolysis depends on(i) their initial concentration(ii) the value of Kh which is Since both of the ions were produced from the same salt, their initial concentrations are same . Therefore unless untial the value of Kw/Kaand Kb is same, the degree of hydrolysis of ion cant be same.To explain why we assume that degree of hydrolysis of cation and anion is same, we need to now look at the third reaction i.e., combination of H+ and OH ions. It is obvious that this reaction happens only because one reaction produced H+ ion and the other produced OH ions. We can also note that this reaction causes both the hydrolysis reaction to occur more since their product ions are being consumed. Keep this thing in mind that the equilibrium which has smaller value of equilibrium conxtant is affected more by the common ion effect. For the same reason if for any reason a reaction is made to occur to a greater extent by the consumption of any one of the product ion, the reaction with the smaller value of equilibrium constant tends to get affected more.Therefore we conclude that firstly the hydrolysis of both the ions ocurs more in the presence of each other (due to consumption of the product ions) than in each other is absence. Secondly the hydrolysis of the ion which occurs to a lesser extent (due to smaller value of Kh) is affected more than the one whose Kh is greater. Hence we can see that the degree of hydrolysis of both the ions would be close to each other when they are getting hydrolysed in the presence of each other.Q.In a solution of NaHCO3 , the amphiprotic anion can under ionization to form H+ ion and hydrolysis to from OH ion.To calculat PH, suitable approximation is

An acetoacetic ester synthesis of a ketone proceeds by alkylation of the enolate of the acetoacetic ester followed by ester hydrolysis and decarboxylation of the -ketoacid. Which of the following methyl ketones is difficult to prepare by this method?a)b)c)d) Correct answer is option 'D'. Can you explain this answer?
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An acetoacetic ester synthesis of a ketone proceeds by alkylation of the enolate of the acetoacetic ester followed by ester hydrolysis and decarboxylation of the -ketoacid. Which of the following methyl ketones is difficult to prepare by this method?a)b)c)d) Correct answer is option 'D'. Can you explain this answer? for JEE 2024 is part of JEE preparation. The Question and answers have been prepared according to the JEE exam syllabus. Information about An acetoacetic ester synthesis of a ketone proceeds by alkylation of the enolate of the acetoacetic ester followed by ester hydrolysis and decarboxylation of the -ketoacid. Which of the following methyl ketones is difficult to prepare by this method?a)b)c)d) Correct answer is option 'D'. Can you explain this answer? covers all topics & solutions for JEE 2024 Exam. Find important definitions, questions, meanings, examples, exercises and tests below for An acetoacetic ester synthesis of a ketone proceeds by alkylation of the enolate of the acetoacetic ester followed by ester hydrolysis and decarboxylation of the -ketoacid. Which of the following methyl ketones is difficult to prepare by this method?a)b)c)d) Correct answer is option 'D'. Can you explain this answer?.
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