QUESTIONS 1. When the alcohol used in the synthesis of isopentyl acetate contain

Question

QUESTIONS 1. When the alcohol used in the synthesis of isopentyl acetate contains a high percentage of oxygen-18 in the oH group, all the oxygen-18 is incorporated into the ester. What are the implications of this for the mechanism of the reaction (hint: write down the mechanism) 2. The equilibrium constant for the reaction CH CO,H HOCH CH. CH CO CH,CH3 H2O has a value of 4. If we heat one ole each of acetic acid and ethanol, what is the maximum amount of ester that will be produced? 3. In the removal of excess acetic acid in the synthesis of isopentyl acetate, why did we use a sodium bicarbonate solution rather than a sodium hydroxide solution? 4. ters can be made by reacting an acid chloride or an acid anhydride with ar conveniently alcohol diye the reaction equations for making isopentyl acetate by these methods.

Explanation / Answer

1)The incorporation of all the O18 in ester part shows the acyl cleavage in the acid and the alcohol is the nucleophile attacking the acyl carbon through the tetrhedral mechanism.

2) Ch3COOH + C2H5Oh <--------> CH3COOC2H5 + H20

1.0 1.0 0 0 initial moles

1-x 1-x x x at equilibrium

thus K = x2/(1-x)2  = 4 (given)

thus x = 2/3 = 0.667 M

The masimum amount of ester formed = 0.667 M

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