Problem 22.2 Part A Compare each of the mechanisms listed here with the mechanis
ID: 693978 • Letter: P
Question
Problem 22.2 Part A Compare each of the mechanisms listed here with the mechanism for each of the two parts of the acid-catalyzed hydrolysis of an ester, indicating Which of the mechanisms have portions that may be compared where a tetrahedral compound is formed from a carbonyl compound? similarities and differences. Select all that apply. 1. acid-catalyzed formation of a hydrate acid-catalyzed conversion of an aldehyde to a hemiacetal . acid-catalyzed conversion of a hemiacetal to an acetal 3, 4. acid-catalyzed hydrolysis of an amideExplanation / Answer
Answer Part A : Acetals(Stable) & Hemiacetals(Unsatable) are essentially tetrahedral intermediates.
In the presence of acid, hemiacetals undergo an elimination reaction and losing the oxygen atom which belonged to the parent aldehyde’s carbonyl group and formed oxonium ions which are powerful electrophiles, and react rapidly with a second molecule of alcohol in order to from new, stable compounds, called acetals.
Acetalsare stable tetrahedral intermediates so they can be used as protective groups in organic synthesis.
Correct option is (3) acid-catalyzed conversion of a hemiacetal to acetal
Rank according to Rate of hydrolysis order at pH = 3.5 from largest to smallest
as rate of hydrolysis decreases with in the concentration of acid and also Electron withdrawing group increases the rate of hydrolysis and have a positive value thus , the order as follows
O-carboxybenzamide(Largest) > O-formylbenzamide > O-hydroxybenzamide > benzamide(smallest)
------> Which is following is a step in the mechanism of the reaction?
as I- is better leaving group as compared to -OH group thus Option II is correct mechanism of the reaction.
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