Organic Chemistry: Carboxylic Acid Derivatives

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1. amide formation 10. carboxylic acid three

from an derivatives
anhydride contain ______
bonds to
heteroatoms
2. amide formation
from an ester 11. carboxylic acid acyl halides > anhydrides >
derivatives carboxylic acids and esters > amides
ranked from most
reactive to least
reactive
12. consequence of the can be interconverted through
3. amide hydrolysis carboxylic acids nucleophilic acyl substitution by
derivatives swapping leaving groups
containing three
bonds to
heteroatoms
13. ester reactions (4) 1. transesterification
2. hydrolysis
requires acid 3. reduction
forms a carboxylic acid 4. saponification
4. amide reactions 1. formation from an anhydride 14. hydrolysis of an
(4) 2. formation from an ester ester
3. hydrolysis (requires acid)
forms a carboxylic acid and an
4. reduction to an amine
alcohol
5. amide reduction
15. intramolecular
to an amine
formation of a
cyclic anhydride
reagent: LiAlH₄
6. anhydride 1. synthesis via dehydration of two
reactions (2) carboxylic acids
2. intramolecular formation of a 16. reduction of an
cyclic anhydride ester

7. anhydride
reagent: LAH
synthesis via
forms two primary alcohols
dehydration of
two carboxylic 17. saponification
acids

18. transesterification

8. a reaction that can occur spontaneously by

proceeds down nucleophilic acyl substitution
the order of
reactivity
9. a reaction that requires special catalysts and
proceeds up the specific reaction conditions
order of reactivity