Quiz 4: Bromination of Acetanilide Flashcards
Is the aromatic ring of acetanilide activated or deactivated toward electrophilic aromatic substitution?
A. activated
B. deactivated
C. neither
D. depends on temperature. An increase of temperature results in increase of activation
A
What is the purpose of acetic acid in bromination of acetanilide reaction?
A. acts as solvent and helps polarize Br-Br bond
B. overall product
C. protonated nitrogen for better nucleophile
D. no specific function
A
What is the purpose of 30% sodium thiosulfate in the bromination reaction of acetanilide to bromoacetanilide?
A. Quench unreacted Br
B. Dissolve unreacted acetanilide
C. dry the product
D. precipitate the product
A
How is the product of the bromination of acetanilide purified?
A. sublimation
B. recrystallization
C. column chromatography
D. distillation
B
How many 13C NMR signals are in: [ortho-product] of the bromination reaction of acetanilide?
A. 6
B. 8
C. 9
D. 5
B
What is the first step in the general mechanism for electrophilic aromatic substitution?
A. protonation of aromatic ring
B. deprotonation of aromatic ring
C. addition of electrophile to aromatic ring
D. loss of electrophile to aromatic ring
C
In the bromination of acetanilide, what is the nucleophile?
A. Br
B. acetic acid
C. acetanilide
D. HBr
C
What is the driving force for losing proton in the last step in the electrophilic aromatic substitution reaction?
A. to neutralize the base
B. make room for electrophile
C. rearomatize ring system
C
What is the Ha splitting pattern in 1H NMR for [para-product] of bromination reaction of acetanilide?
A. doublet
B. triplet
C. singlet
D. doublet of doublet
A
How many 1H NMR signals are in [para-product]?
A. 4
B. 5
C. 3
D. 6
A
What is the theoretical yield of the brominated product if 600 mg of acetanilide and 1.0 mL of 4.1 M bromine solution in acetic acid is used? (MW of acetanilide: 135.16 g/mol | MW of Br2 in glacial acetic acid: 159.8 g/mol | MW of final product: 214.06 g/mol)
878 mg
