EXERCISE 7

Question 1

• an amide obtained by ACETYLATION of ANILINE
• the FIRST aniline derivative found to posses analgesic-antipyretic properties
• introduced into medical practice under the name of ANTIFEBRIN
• not used directly for this application due to METHEMOGLOBINEMIC effect

Answer 1

ACETANILIDE

Question 2

ACETANILIDE

obtained by ____

Answer 2

acetylation of aniline

Question 3

ACETANILIDE

the FIRST aniline derivative found to posses ____ properties

Answer 3

analgesic-antipyretic

Question 4

ACETANILIDE

introduced into medical practice under the name of ____

Answer 4

antifebrin

Question 5

ACETANILIDE

NOT used directly as due to ____ effect

Answer 5

methemoglobinemic

Question 6

ACETANILIDE

was first used as an ____ drug

Answer 6

antipyretic-analgesic

Question 7

ACETANILIDE

it is metabolized inside the body into its active form – ____

Answer 7

ACETAMINOPHEN

Question 8

ACETANILIDE

active form

Answer 8

ACETAMINOPHEN

Question 9

ACETANILIDE

SMALL PORTIONS of acetanilide is metabolized into ____ through a different pathway

a DISADVANTAGE

Answer 9

ANILINE

Question 10

ACETANILIDE

aniline causes ____

Answer 10

METHEMOGLOBINEMIA

Question 11

ACETANILIDE | SIDE EFFECTS

DIRECT skin and eye contact will result in severe ____

Answer 11

IRRITATION

Question 12

ACETANILIDE | SIDE EFFECTS

can cause ____ and ____ of the RESPIRATORY TRACT

Answer 12

skin allergies and irritation

Question 13

ACETANILIDE | SIDE EFFECTS

more SERIOUS effects may include ____

Answer 13

BLOOD ABNORMALITIES

Question 14

ACETANILIDE |USES

____ of PEROXIDES

Answer 14

inhibitor

Question 15

ACETANILIDE |USES

____ for CELLULOSE ESTER varnishes

Answer 15

stabilizer

Question 16

ACETANILIDE |USES

intermediate for the synthesis of ____

Answer 16

rubber accelerators

Question 17

ACETANILIDE |USES

PRECURSOR in ____ synthesis

Answer 17

PENICILLIN SYNTHESIS

Question 18

ACETANILIDE |USES

PRECURSOR in ____ and its intermediates

Answer 18

PAINKILLERS

Question 19

ACETANILIDE | REAGENTS

• clear colorless oily liquid but DARKENS on exposure to LIGHT and AIR
• LIMITING REACTANT in the reaction
• act as a NUCLEOPHILE (donates its electron pair to an electrophile)
• when heated with organic acid yields anilide

Answer 19

ANILINE

Question 20

ACETANILIDE | REAGENTS | ANILINE

acts as ____

Answer 20

NUCLEOPHILE

Question 21

ACETANILIDE | REAGENTS | ANILINE

when HEATED with an organic acid, it yields ____

Answer 21

ANILIDE

Question 22

ACETANILIDE | REAGENTS

• colorless liquid with STRONG VINEGAR-like odor
• LACHRYMATOR; IRRITANT
• hydrolyzed into two acetic acid molecules upon reaction with the moisture in air
• source of the acyl (-COR) group used to acetylate the aniline to produce acetanilide

Answer 22

ACETIC ANHYDRIDE

Question 23

ACETANILIDE | REAGENTS | ACETIC ANHYDRIDE

is the source of the ____ group used to acetylate the aniline to produce acetanilide

Answer 23

acyl (-COR)

Question 24

ACETANILIDE | REAGENTS

• activated carbon
• has HIGH DEGREE OF MICROPOROSITY – high surface area
• removes HMW IMPURITIES, usually colored impurities and relatively less soluble on the solvent

Answer 24

ACTIVATED CHARCOAL

Question 25

# **ACETANILIDE | SYNTHESIS** ____ and ____ is mixed in an erlenmeyer flask

Answer 25

aniline and distilled water

Question 26

# **ACETANILIDE | SYNTHESIS** ____ is added **dropwise** while swirling to ensure that all the aniline will react with the acetic acid

Answer 26

acetic anhydride

Question 27

# **ACETANILIDE | SYNTHESIS** solution is ____ unti **all** solids or oil **dissolves**

Answer 27

heated

Question 28

# **ACETANILIDE** REACTION INVOLVED

Answer 28

nucleophilic acyl substitution (addition/elimination)

Question 29

# **ACETANILIDE | NUCLEOPHILIC ACYL SUBSTITUTION** the **ACYL group** from the acetic anhydride acts as an ____

Answer 29

electrophile

Question 30

# **ACETANILIDE | SYNTHESIS** ____ is added **after** the solids or the oil **dissolves**

Answer 30

activated charcoal

Question 31

# **ACETANILIDE | SYNTHESIS** solution is then **filters** using a **fluter filter paper** to **minimize** ____

Answer 31

PREMATURE CRYSTALLIZATION

Question 32

# **ACETANILIDE | SYNTHESIS** **FILTRATE** must be ____ with clear colorless solution

Answer 32

decolorized

Question 33

# **ACETANILIDE | SYNTHESIS** allow the solution to cool slowly then **induce more crystals** by ____

Answer 33

ICE BATH

Question 34

# **ACETANILIDE | SYNTHESIS** crystals obtained are **dried** in an **oven** at what temperature

Answer 34

105 C

Question 35

# **ACETANILIDE | TESTS** COLOR

Answer 35

WHITE

Question 36

# **ACETANILIDE | TESTS** ODOR

Answer 36

ODORLESS

Question 37

# **ACETANILIDE | TESTS** APPEARANCE

Answer 37

SOLID FLAKES or CRYSTALLINE POWDER

Question 38

# **ACETANILIDE | TESTS** MELTING POINT

Answer 38

114.3 C

Question 39

# **ACETANILIDE** IUPAC name

Answer 39

N-phenylacetamide

Question 40

# **ACETANILIDE** SYNONYM

Answer 40

acetanil, acetylaniline

Question 41

# **ACETANILIDE** MOLECULAR FORMULA

Answer 41

C₈H₉NO

Question 42

# **ACETANILIDE** PHYSICAL DESCRIPTION

Answer 42

odorless white crystalline powder

Question 43

# **ACETANILIDE** MOLECULER WEIGHT

Answer 43

135.16 g/mol

Question 44

# **ACETANILIDE** BOILING POINT

Answer 44

304 C

Question 45

# **ACETANILIDE** SOLUBILITY

Answer 45

6.93x10³ mg per 1L water at 25C

Question 46

# **ACETANILIDE** DENSITY

Answer 46

1.219 g/cm³

Question 47

# **ACETANILIDE** CHEMICAL SAFETY

Answer 47

irritant

Question 48

# **ACETANILIDE** STABILITY

Answer 48

can undergo self-ignition at 545 C

Question 49

# **ACETANILIDE** STRUCTURE

Answer 49

amide group attached in a benzene ring