ex 7 synthesis of acetanilide

acetanilide

an amide obtained by acetylation of aniline

acetanilide

the first aniline derivative found to possess analgesic-antipyretic properties

Antifebrin

acetanilide is introduced into medical practice under the name of __

methemoglobinemic

acetanilide is not used directly for this application due to __ effect

antipyretic-analgesic

acetanilide was first used as an __ drug

acetaminophen; aniline

acetanilide s metabolized inside the body into its active form, __

however, small portions of acetanilide is metabolized into __through a different pathway

methemoglobinemia

aniline causes __ (methemoglobin instead of hemoglobin)

• direct skin and eye contact will result in severe irritation

• can cause skin allergies and irritation of the respiratory tract

• more serious effects may include blood abnormalities

side effects of acetanilide

acetanilide

precursor in penicillin synthesis

acetanilide

precursor in painkillers and its intermediates

acetanilide

inhibitor of peroxides and stabilizer for cellulose ester varnishes

acetanilide

intermediate for the synthesis of rubber accelerators, dye intermediates and camphor

aniline

clear colorless oily liquid but darkens on exposure to light and air

aniline

limiting reactant in the reaction (acetanilide)

nucleophile

aniline acts as a __(donates its electron pair to an electrophile)

anilide

aniline when heated with organic acid yields __

acetic anhydride

colorless liquid with strong vinegar-like odor

acetic anhydride

lachrymator; irritant

two acetic acid molecules

acetic anhydride hydrolyzed into __ upon reaction with the moisture in air

acetic anhydride

source of the acyl (–COR) group used to acetylate the aniline to produce acetanilide

activated charcoal

activated carbon

activated charcoal

• has high degree of microporosity – high surface area

• removes HMW impurities, usually colored impurities and relatively less soluble on the solvent

acetic anhydride; heated; activated charcoal; ice bath; 105°C

synthesis of acetanilide

• aniline and distilled water is mixed in an Erlenmeyer flask

• __ is added dropwise while swirling to ensure that all the aniline will react with the acetic acid

• solution is __ until all solids or oil dissolves

• __ is added after the solids or the oil dissolves

• solution is then filtered using a fluted filter paper to minimize premature crystallization

• filtrate must be decolorized, with clear colorless solution

• allow the solution to cool slowly then induce more crystals by __

• the flask is removed from the ice bath

• the crystals are filtered

• crystals obtained are dried in an oven at __ and are weighed

• percentage yield is computed

• nucleophilic acyl substitution (addition/elimination)

• aniline acts as a nucleophile, and the acyl group from the acetic anhydride acts as an electrophile

reaction involved in the synthesis of acetanilide

• color: white

• odor: odorless

• appearance: solid flakes or crystalline powder

physical test of acetanilide (color, odor, and appearance)

114.3°C

melting point of acetanilide

impurities

(acetanilide) the actual melting point may be lower due to presence of __ in the acetanilide crystals

N-phenylacetamide

synonym: acetanil, acetylaniline

IUPAC name of Acetanilide

Acetanilide

C₈H₉NO

C₈H₉NO

molecular formula of acetanilide

• physical description: odorless white crystalline powder

• molecular weight: 135.16 g/mol

• boiling point: 304°C

• melting point: 114.3°C

physical pro[erties of acetanilide (description, MW, BP, MP)

6.93×103 mg per 1 L water at 25°C

solubility of acetanilide

1.219 g/cm₃

density of acetanilide

irritant

chemical safety of acetanilide

545°C

stability of acetanilide: can undergo self-ignition at __, but is otherwise stable under most conditions

amide group attached in a benzene ring

structure of acetanilide