Question

In: Chemistry

m-toluic acid is first reacted with thionyl chloride in the presence of catalytic pyridine to prepare...

m-toluic acid is first reacted with thionyl chloride in the presence of catalytic pyridine to prepare m-toluoyl chloride, which is then immediately reacted with diethylamine to produce the desired amide, N,N-diethylm-toluamide.

a) What is the driving force for the reaction between the carboxylic acid and thionyl chloride to form the acid chloride?

b) Why is pyridine added to the reaction mixture? Explain the role of the pyridine with respect to the reaction mechanism and expected reaction intermediates.

c) What is the identity of the “white smoke” produced when the ethereal solution of diethylamine is added to the acyl chloride? Support your answer by writing a balanced reaction.

d) Sketch the expected appearance of the 1 H NMR spectrum of DEET. Include approximate chemical shifts, signal multiplicity, and integration value expected for unique set of protons in the

e) What impurities may be present in the DEET that you prepared? List the expected appearance of the signals due to these impurites in the 1 H NMR spectrum of the product.

f) A student dissolved the diethylamine in reagent-grade diethyl ether instead of anhydrous diethyl ether. How would this change affect the reaction outcome?

Solutions

Expert Solution

a) here good leaving group is formed which is driving force of the reaction

b) pyridine abstract the acidic H which is later taken by chloride ion.

c) HCl gas is formed here which is the white smoke.

d) the NMR shift has shown on answer.

e) m toluic acid is impurity whose peak in NMR appears at 11 ppm.

f) if anhydrous is not used then acid chloride hydrolised to acid , further reaction with amine slow down.


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