ОН H, SO, → product Step 1: Use curved arrows to complete the Step 2: Use a curved arrow to show the formation protonation mechanism of the alcohol. of the carbocation intermediate. Note: HSO, is formed from step 1, but not shown. Select Draw Rings More Erase Select Draw Rings More Erase C H C H :0: H H - O - II : o :

Organic Chemistry
9th Edition
ISBN:9781305080485
Author:John E. McMurry
Publisher:John E. McMurry
Chapter16: Chemistry Of Benzene: Electrophilic Aromatic Substitution
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Problem 77AP
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- For the dehydration shown, use curved arrows to show the formation of the carbocation intermediate in the presence of sulfuric acid H2SO4H2SO4, then draw the structure of the major product of the elimination.

(Picture 1):

Step 1: Use curved arrows to complete the protonation mechanism of the alcohol.
Step 2: Use a curved arrow to show the formation of the carbocation intermediate. Note: HSO−4HSO4− is formed from step 1, but not shown.
 
(Picture 2):
Step 3: Use a curved arrow to show the carbocation rearrangement.
Step 4: Draw curved arrows to show the elimination to form the major product. Water is added as a base.
 
- Draw the major product of the elimination. H3O+H3O+ has been pre‑drawn for your convenience.
ОН
H, SO4
→ product
Step 1: Use curved arrows to complete the
Step 2: Use a curved arrow to show the formation
protonation mechanism of the alcohol.
of the carbocation intermediate. Note: HSO is
formed from step 1, but not shown.
Select
Draw
Rings
More
Erase
Select
Draw
Rings
More
Erase
C
H
S
C
H.
:0 :
H - o
0 - H
|
↑
:0 :
:o :
=S= o
:o:
Transcribed Image Text:ОН H, SO4 → product Step 1: Use curved arrows to complete the Step 2: Use a curved arrow to show the formation protonation mechanism of the alcohol. of the carbocation intermediate. Note: HSO is formed from step 1, but not shown. Select Draw Rings More Erase Select Draw Rings More Erase C H S C H. :0 : H - o 0 - H | ↑ :0 : :o : =S= o :o:
H
H
H.
Draw the major product of the elimination. H, o* has
been pre-drawn for your convenience.
Select
Draw
Rings
More
Erase
C
H
H
|
H
H
↑
Transcribed Image Text:H H H. Draw the major product of the elimination. H, o* has been pre-drawn for your convenience. Select Draw Rings More Erase C H H | H H ↑
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