Complete the mechanism of the Hofmann rearrangement that occurs when the given amide is treated with sodium hydroxide and bromine. Add any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Do not delete any of the pre-drawn bonds, charges, or electrons. Step 1: Complete the mechanism of the initial step of the reaction of the amide with sodium hydroxide to form the amidate by adding curved arrows. Select Draw Templates More / |||||| с H N Na Na+ | H O :0 - Erase Q2Q 11 Step 2: The amidate then reacts with bromine to form the haloamide. Use curved arrows to show the reaction with bromine. Select Draw Templates More / |||||| Na + с H Br N Na :0 H I H I H : Br I :: Br Erase 0 Q2Q

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Macmillan Learning
+NaOH,
NaBr
_NaBr, –IO
Step 3: Complete the structure of the
haloamide, and use curved arrows to show
the conversion to the haloamidate in the
next step.
Select Draw Templates More
(+
CHBr N Na 0
H
Na +
LO!
Erase
:0 H
Q2 Q
Step 5: Complete the structure of
the isocyanate.
Select Draw Templates More
/||||||| C N
0
Erase
11
Step 4: Use three curved arrows to show the
rearrangement to form the isocyanate.
Select Draw Templates More
Q
H₂O
с
Br N Na 0
:0 H
H
Na
O
Erase
2 Q
The isocyanate is subsequently hydrated with water to form
the carbamic acid, which then decomposes to the amine and
carbon dioxide.
NH₂
0"]
Transcribed Image Text:Macmillan Learning +NaOH, NaBr _NaBr, –IO Step 3: Complete the structure of the haloamide, and use curved arrows to show the conversion to the haloamidate in the next step. Select Draw Templates More (+ CHBr N Na 0 H Na + LO! Erase :0 H Q2 Q Step 5: Complete the structure of the isocyanate. Select Draw Templates More /||||||| C N 0 Erase 11 Step 4: Use three curved arrows to show the rearrangement to form the isocyanate. Select Draw Templates More Q H₂O с Br N Na 0 :0 H H Na O Erase 2 Q The isocyanate is subsequently hydrated with water to form the carbamic acid, which then decomposes to the amine and carbon dioxide. NH₂ 0"]
Organic Chemistry
Maxwell
presented by Macmillan Learning
Complete the mechanism of the Hofmann rearrangement that occurs when the given amide is treated with sodium hydroxide
and bromine. Add any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Do not delete any of the
pre-drawn bonds, charges, or electrons.
Step 1: Complete the mechanism of the initial step of
the reaction of the amide with sodium hydroxide to
form the amidate by adding curved arrows.
Select Draw Templates More
/ |||||| с
H N Na
Na
I
H
H
O
H
Erase
Q2Q
11
Step 2: The amidate then reacts with bromine to
form the haloamide. Use curved arrows to show
the reaction with bromine.
Select Draw Templates More
/ ||||||||| C
→
Na
с H
:0 - H
I
H
N:
Br N
1
H
Na
: Br Br
Erase
O
Q2 Q
Transcribed Image Text:Organic Chemistry Maxwell presented by Macmillan Learning Complete the mechanism of the Hofmann rearrangement that occurs when the given amide is treated with sodium hydroxide and bromine. Add any missing atoms, bonds, charges, nonbonding electron pairs, and curved arrows. Do not delete any of the pre-drawn bonds, charges, or electrons. Step 1: Complete the mechanism of the initial step of the reaction of the amide with sodium hydroxide to form the amidate by adding curved arrows. Select Draw Templates More / |||||| с H N Na Na I H H O H Erase Q2Q 11 Step 2: The amidate then reacts with bromine to form the haloamide. Use curved arrows to show the reaction with bromine. Select Draw Templates More / ||||||||| C → Na с H :0 - H I H N: Br N 1 H Na : Br Br Erase O Q2 Q
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