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Carboxylic Acid Derivatives
Compounds in which an acyl group is bonded to an electronegative atom or substituent that can act as a leaving group in the nucleophilic acyl substitution reaction
Acid Halides
neutral compounds that reacts with water to produce an acid and hydrogen halide
Carboxylic acids and from sulfonic acid
The most important organic halides are the chlorides derived from ______
Acid Halides
They have sharp odours and irritate the mucous membranes.
Acetic anhydride
(CH3CO)2O
Acetic anhydride
often used to prepare acetate esters from alcohols.
aspirin
(acetylsalicylic acid)
aspirin
prepared commercially by the acetylation of o-hydroxybenzoic acid with acetic anhydride.
(salicylic acid)
o-hydroxybenzoic acid
Blue to red
Acetyl Chloride + Cold Water (Color of litmus paper)
Hot / Warm
Acetyl Chloride + Cold Water (How does the outside of test tube feel)
Milky Solution
Acetyl Chloride + Cold Water (Add silver nitrate and water) what forms?
Plastic Balloon
Acetyl Anhydride + Ethyl Alcohol (odor)
Plastic Balloon
Acetic Anhydride + Ethyl Alcohol (odor)
White Precipitate
Acetyl Chloride + Aniline
White Precipitate
Acetic Chloride + Aniline
Strong reaction; Formation of Two Layers
Acetic anhydride + NaOH
Acetic anhydride is more preferred because it does not react violently as acetyl chloride.
1.Both acetyl chloride and acetic anhydride are good acetylating agents. Which is more preferred and why?
Acetylation
in IUPAC nomenclature ethanoylation
Acetylation
describes a reaction that introduces an acetyl functional group into an organic compound.
Deacetylation
removal of the acetyl group.
N-Phenylacetamide, C8H9NO
2.Give the structural formula of acetanilide
acetanilide
synthetic organic compound introduced in therapy in 1886 as a fever-reducing drug
acetanilide
relieves pain
acetanilide
was used as an alternative to aspirin for many years in treating such common complaints as headache, menstrual cramps, and rheumatism
it interferes with the function of hemoglobin, the oxygen-carrying pigment of the blood.
Excessive or prolonged use of acetanilide engenders toxic side effects:
Acetaminophen
In the body, acetanilide is mostly converted to ______ because it is less likely to induce blood disorders.
Silver nitrate test
3.What single test can be used to distinguish acetyl chloride from acetic anhydride?
white precipitate
Acetyl chloride and silver nitrate (AgNO3) produces
no reaction
Acetic anhydride and silver nitrate (AgNO3)
