What is the expected product of the given monobromination EAS reaction? (See p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.) This aromatic ring is considered to be "activated" for electrophilic aromatic substitution. Draw resonance structures of acetanilide to determine if the NH- C(O)CH3 group is electron-donating or electron-withdrawing.

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Aromatic Bromination and Green Chemistry
Two step synthesis and identification of product
Will use vacuum filtration and analysis with m.p., IR, and NMR
Day 1: Protection of Aniline Nitrogen
(Amide Formation)
●
Modifying aniline through
reaction with acetic anhydride
Day 2: Aromatic Bromination
Monobromination of an activated
aromatic compound
Evaluation of directing effects by
the isomeric product obtained
Modification of procedure from Luong et al,
J. Chem Ed. 2012, 89, 1061-1063
NH₂
aniline
NH
NaBr, NaClO
AcOH, EtOH
acetanilide
para
NH
ΝΗ
Br
ortho
meta
Which position is brominated?
(ortho, meta, or para)
Transcribed Image Text:● ● Aromatic Bromination and Green Chemistry Two step synthesis and identification of product Will use vacuum filtration and analysis with m.p., IR, and NMR Day 1: Protection of Aniline Nitrogen (Amide Formation) ● Modifying aniline through reaction with acetic anhydride Day 2: Aromatic Bromination Monobromination of an activated aromatic compound Evaluation of directing effects by the isomeric product obtained Modification of procedure from Luong et al, J. Chem Ed. 2012, 89, 1061-1063 NH₂ aniline NH NaBr, NaClO AcOH, EtOH acetanilide para NH ΝΗ Br ortho meta Which position is brominated? (ortho, meta, or para)
What is the expected product of the given monobromination EAS reaction? (See
p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.)
This aromatic ring is considered to be "activated" for electrophilic aromatic
substitution. Draw resonance structures of acetanilide to determine if the NH-
C(O)CH3 group is electron-donating or electron-withdrawing.
Transcribed Image Text:What is the expected product of the given monobromination EAS reaction? (See p 316-317 if you haven't studied aromatic chemistry yet in CHEM 241B.) This aromatic ring is considered to be "activated" for electrophilic aromatic substitution. Draw resonance structures of acetanilide to determine if the NH- C(O)CH3 group is electron-donating or electron-withdrawing.
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