Quiz - Carboxylic Acid Derivatives | Carboxylic Acid Derivatives - Part 1
What is the order of reactivity of the carboxylic acid derivatives from the least reactive to the most reactive?
Carboxylic anhydrides < esters < amides < acyl halides
Esters < amides < acyl halides < carboxylic anhydrides
Amides < esters < carboxylic anhydrides < acyl halides
Acyl halides < carboxylic anhydrides < esters < amides
Which carboxylic acid derivative has the most acidic proton on the α-carbon?
Ester
Amide
Carboxylic anhydride
Acyl halide
The pKa of hydrogens on the α-carbon depends on the electronegativity of the group attached to the C=O bond ⇒ the lower the electronegativity, the higher the pKa. Acyl halide: pKa ~ 16; Carboxylic anhydride: pKa ~ 20; Ester: pKa ~ 25; Amide: pKa ~ 30
What is the typical chemical reaction of carboxylic acid derivatives?
Substitution nucleophile
Addition - elimination
Reduction
Oxidation
Which of the following reagents converts an ester to an aldehyde?
DIBAL-H
CH3MgBr
LiAlH4
NaOH / H2O
What are the starting reagents of a transesterification?
2 esters
Carboxylic acid + ester
Carboxylic acid + alcohol
Ester + alcohol
Mechanism of transesterification:
Which of the following reagents converts an amide to an amine?
DIBAL-H
CH3MgBr
LiAlH4
H2SO4 / H2O
