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Rank the following compounds in order of their reactivity toward nucleophilic acyl substitution. (Fastest first, slowest last) 2) (10 pts) Rank the following compounds in order of the following sets with respect to increasing acidity. (Least acidic first, most acidic last) b) Benzoic acid, para-nitrobenzoic acid, trinitrobenzoic acid 3) (5 pts) How can you explain the fact that 2-chlorobutanoic acid has a pKa- 2.86,3- chlorobutanoic acid has a pKa 4.05, 4-chlorobutanoic acid has a pKa-4.52, and butanoic acid itself has a pKa 4.82? BRIEFLY EXPLAIN USING NO MORE THEN 3 SENTENCES. DRAWING THE STRUCTURES WHILE EXPLAINING WILL PROBABLY HELP

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InesWalston

Answer:

Trinitrobenzoic acid > para nitro benzoic acid>benzoic acid

Nulceophilic acyl Substitution increases by electron withdrawing group (NO2) more the no of withdrawing groups more the reactivity

Since withdrawing group increases positive charge hence nucleophilie readily reacts.

Acidity of Carboxylic acid is explained by inductive effect

Withdrawing group (halogen) increases the acidity and acidity decreases with increasing the distance between halogen and COOH group

And lower the acidity higher the pka and Vice-Versa.

Hence 2-Chlorobutanoic acid has lower pka and more acidic than 3-chloro and 4-chlorobutanoic acids

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