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Chapter 15: Q47P (page 724)

How could you synthesize the following compounds starting with a carboxylic acid?

Short Answer

Expert verified

The reaction followed as:

b.

Step by step solution

01

Formation of ether from carboxylic acid

Carboxylic acid directly does not lead to ether formation of carboxylic acid derivate is formed that is acyl chloride on the reaction of a carboxylic acid with the thionyl chloride or phosphorous trichloride after abstraction of proton of carboxylic acid they attached to it and make a good leave group and form acyl chloride which on reaction with alcohol from the ether.

02

Mechanism

Mechanism followed as:

  1. Reaction of a carboxylic acid with thionyl chloride

  2. Formation of acyl chloride occur

  3. Reaction of an acyl chloride with alcohol

  4. Removal of HCl occur

  5. Formation of ether occurred

03

Formation of amide from carboxylic acid

Similarly, a carboxylic acid forms its derivative acyl chloride on reaction with thionyl chloride, and the reaction followed by reacting with two equivalent amines and amide formation occurs followed by removal of HCl as followed:

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Most popular questions from this chapter

Question: Show how the following compounds could be prepared from the given starting materials. You can use any necessary organic or inorganic reagents.

a.

b.

c.

d.

Write the mechanism for the acid-catalyzed reaction of an amide with an alcohol to form an ester.

Information about the mechanism of the reaction undergone by a series of substituted benzenes can be obtained by plotting logarithm of the observed rate constant determined at particular pH against the Hammett substituent constant蟽 for the particular substituent. The 蟽value for hydrogen is zero. Electron-donating substituents have negative蟽 values; the more strongly electron withdrawing the substituent, the more positiveits s value. The slope of a plot of the logarithm of the rate constant 蟽versusis called the蚁 (rho) value. The 蚁value for the hydroxide-ion-promoted hydrolysis of a series of meta- and para-substituted ethyl

benzoates is +2.46; the蚁 value for amide formation for the reaction of a series of meta- and para-substituted anilines with benzoyl chloride is -2.78.

  1. Why doesone set of experiments give a positive role="math" localid="1652525783964" 蚁value, whereas the other set of experiments gives a negative蚁 value?
  2. Why were ortho-substituted compounds not included in the experiment?
  3. What do you predict the sign of the蚁 value to be for the ionization of a series of meta- and para-substituted benzoic acids?

a.Identify the two products obtained from the following reaction:

b. A student carried out the preceding reaction, but stopped it before it was half over, whereupon he isolated the major product. He was surprised to find

that the product he isolated was neither of the products obtained when the reaction was allowed to go to completion. What product did he isolate?

The aromas of many flowers and fruits are due to esters such as those shown in this problem. What are the common names of these esters? (Also see Problem 57.)
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