D. The mechanism for the reaction of t-butyl alcohol with sulfuric acid is shown below. i) Draw arrows showing the electron flow for this reaction on the structures provided below. Step 1: CH₂ CH₂-C-0-H + H-O-S-OH → CH3 B. Step 2: Step 3: H₂O: CH3 H of on CH₂-C -0+ + HSO H CH3 CH3 CH₂-C-0+ CH3 H H H H H CH3 48 H-C H CH3 CH3 CH₂-C H CH3 CH3 + H₂Ö: ii) Circle the correct answer(s): This reaction occurs via: SN1 SN2 E1 E2 borderline SN2 CH3 CH3 iii) Provide the structure of the major product that would be formed if HCI would be used instead of sulfuric acid: iv) Above the arrow (in the picture below) provide all the necessary reagents and specific reaction conditions (other than oxymercuration-demercuration) that would allow you to successfully convert the alkene back to the alcohol: CH3 + H₂O+ CH3 CH₂-C-0-H CH₂

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D. The mechanism for the reaction of t-butyl alcohol with sulfuric acid is shown
below. i) Draw arrows showing the electron flow for this reaction on the
structures provided below.
Step 1:
CH3
CH₂-C-Ö-H +H-O-S-OH
of on
CH3
Step 2:
Step 3:
H₂Ö:
CH₂
CH, H
H
CH3
H
H
H-C
ii) Circle the correct answer(s):
This reaction occurs via: SN1
H
H
CH3
CH3
CH3
←
CH₂
CH₂
Page 7
H
CH3 H
CH3
CH3
CH3
H
+ HỘ:
CH3
SN2 E1 E2 borderline SN2
iii) Provide the structure of the major product that would be formed if HCI would
be used instead of sulfuric acid:
+ HSO
CH3
iv) Above the arrow (in the picture below) provide all the necessary reagents
and specific reaction conditions (other than oxymercuration-demercuration)
that would allow you to successfully convert the alkene back to the alcohol:
CH3
+ H₂O+
CH3
CH₂-C-O-H
CH₂
Transcribed Image Text:D. The mechanism for the reaction of t-butyl alcohol with sulfuric acid is shown below. i) Draw arrows showing the electron flow for this reaction on the structures provided below. Step 1: CH3 CH₂-C-Ö-H +H-O-S-OH of on CH3 Step 2: Step 3: H₂Ö: CH₂ CH, H H CH3 H H H-C ii) Circle the correct answer(s): This reaction occurs via: SN1 H H CH3 CH3 CH3 ← CH₂ CH₂ Page 7 H CH3 H CH3 CH3 CH3 H + HỘ: CH3 SN2 E1 E2 borderline SN2 iii) Provide the structure of the major product that would be formed if HCI would be used instead of sulfuric acid: + HSO CH3 iv) Above the arrow (in the picture below) provide all the necessary reagents and specific reaction conditions (other than oxymercuration-demercuration) that would allow you to successfully convert the alkene back to the alcohol: CH3 + H₂O+ CH3 CH₂-C-O-H CH₂
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