Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. CH3 0 Diene + Dienophile → + ...l ChemDoodleⓇ CN CN CH3 • Consider E/Z stereochemistry of alkenes. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. CN CN

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Chapter1: Chemical Foundations
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Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown.
CH3
0
Diene + Dienophile
ChemDoodleⓇ
CH3
CN
CN
Sn [F
-CN
• Consider E/Z stereochemistry of alkenes.
• Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
• Separate multiple products using the + sign from the drop-down menu.
CN
Transcribed Image Text:Draw structural formulas for the diene and dienophile that combine in a Diels-Alder reaction to form the product shown. CH3 0 Diene + Dienophile ChemDoodleⓇ CH3 CN CN Sn [F -CN • Consider E/Z stereochemistry of alkenes. • Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. • Separate multiple products using the + sign from the drop-down menu. CN
The reaction below shows 1,2- and 1,4-addition to a conjugated diene.
H
CH₂=CH-CH=CH₂ + H-Br
1,3-Butadiene
C
H
H
XT
H
Draw curved arrows to show the movement of electrons in the step of the mechanism shown below.
Arrow-pushing Instructions
NAN
H
-78°C
+ H-Br
Br
H
H
CH₂-C-CH=CH₂
3-Bromo-1-butene
(90%)
(1,2-addition)
Br
H
H
jfs-yybjff
H
H
Allylic carbocation stabilized by resonance
CH₂CH=CH-CH₂
1-Bromo-2-butene
(10%)
(1,4-addition)
H
H
H
H
H
H
H
H
H
Transcribed Image Text:The reaction below shows 1,2- and 1,4-addition to a conjugated diene. H CH₂=CH-CH=CH₂ + H-Br 1,3-Butadiene C H H XT H Draw curved arrows to show the movement of electrons in the step of the mechanism shown below. Arrow-pushing Instructions NAN H -78°C + H-Br Br H H CH₂-C-CH=CH₂ 3-Bromo-1-butene (90%) (1,2-addition) Br H H jfs-yybjff H H Allylic carbocation stabilized by resonance CH₂CH=CH-CH₂ 1-Bromo-2-butene (10%) (1,4-addition) H H H H H H H H H
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