Complete the curved arrow pushing mechanism of the reaction of butanal in ethylene glycol and hydrogen chloride by adding any missing curved arrows. A generic base, B:, is used as a proton shuttle. Step 1: Add curved arrows. Select Draw Templates More :: : Cl H G Select Draw Templates More C H O Cl → Step 3: add curved arrows. Recall that B: represents a generic base. :J: : 0: C H O : OH H Cl H 2 Q B Erase Erase OH : B Ⓡ 2 Q 11 Step 2: add curved arrows. Select Draw Templates More : Step 4: add curved arrows. C H O : Cl Select Draw Templates More → : 5: C H Cl O H Q2 Cl الر کرد B Erase O Erase HB + OH 2 Q

Organic Chemistry: A Guided Inquiry
2nd Edition
ISBN:9780618974122
Author:Andrei Straumanis
Publisher:Andrei Straumanis
Chapter15: Radical Reactions
Section: Chapter Questions
Problem 5CTQ
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Question
Complete the curved arrow pushing mechanism of the reaction of butanal in ethylene glycol and hydrogen chloride by adding
any missing curved arrows. A generic base, B:, is used as a proton shuttle.
Step 1: Add curved arrows.
Select Draw Templates More
/
: CLH
/
G
Select Draw Templates More
C H
: Cl :
45
C
O
Step 3: add curved arrows. Recall that B:
represents a generic base.
H
:ỗ :
HO
: 0:
Cl
O
: OH
H
Ⓡ 2 Q
كلت
Cl B
H
Erase
OH
Erase
: B
2 Q
11
12
Step 2: add curved arrows.
Select Draw Templates More
G
CL :
C H
Step 4: add curved arrows.
: Cl :
Select Draw Templates More
C
H
O
0:
O Cl
H
O
Q 2 Q
Cl B
Erase
: 0:
H B
: 5:
Erase
2 Q
OH
: 8:
Transcribed Image Text:Complete the curved arrow pushing mechanism of the reaction of butanal in ethylene glycol and hydrogen chloride by adding any missing curved arrows. A generic base, B:, is used as a proton shuttle. Step 1: Add curved arrows. Select Draw Templates More / : CLH / G Select Draw Templates More C H : Cl : 45 C O Step 3: add curved arrows. Recall that B: represents a generic base. H :ỗ : HO : 0: Cl O : OH H Ⓡ 2 Q كلت Cl B H Erase OH Erase : B 2 Q 11 12 Step 2: add curved arrows. Select Draw Templates More G CL : C H Step 4: add curved arrows. : Cl : Select Draw Templates More C H O 0: O Cl H O Q 2 Q Cl B Erase : 0: H B : 5: Erase 2 Q OH : 8:
Step 5: A curved arrow is pre-drawn for you.
Add a second curved arrow to show loss of the
leaving group.
Select Draw Templates More
: Cl :
G
H
✔
G
Step 7: Add curved arrows.
Select Draw Templates More
C
: Cl :
H
H
с
H
O Cl
: B
H
B
Q2 Q
O Cl B
: B
Erase
H
Erase
Q2 Q
14
11
Step 6: add curved arrows.
Select Draw Templates More
/
: Cl :
5
: CL :
H
C
Select Draw Templates More
✔
H
: B
Step 8: complete the final product.
O
C H
Cl
Q 2
H10:
H
H
B
Erase
O Cl B
o
Erase
Ⓡ 2 Q
Transcribed Image Text:Step 5: A curved arrow is pre-drawn for you. Add a second curved arrow to show loss of the leaving group. Select Draw Templates More : Cl : G H ✔ G Step 7: Add curved arrows. Select Draw Templates More C : Cl : H H с H O Cl : B H B Q2 Q O Cl B : B Erase H Erase Q2 Q 14 11 Step 6: add curved arrows. Select Draw Templates More / : Cl : 5 : CL : H C Select Draw Templates More ✔ H : B Step 8: complete the final product. O C H Cl Q 2 H10: H H B Erase O Cl B o Erase Ⓡ 2 Q
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