Noting the curved arrows, draw all the product(s), organic and inorganic, of the following reaction. H3C CH3 • You do not have to consider stereochemistry. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu.

Organic Chemistry: A Guided Inquiry
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ISBN:9780618974122
Author:Andrei Straumanis
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Chapter19: Eas: Electrophilic Aromatic Substitution
Section: Chapter Questions
Problem 31CTQ
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Noting the curved arrows, draw all the product(s), organic and inorganic, of the following reaction.
H3C
CH3
You do not have to consider stereochemistry.
Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner.
Separate structures with + signs from the drop-down menu.
P
opy
aste
?
ChemDoodle®
Transcribed Image Text:Noting the curved arrows, draw all the product(s), organic and inorganic, of the following reaction. H3C CH3 You do not have to consider stereochemistry. Draw one structure per sketcher. Add additional sketchers using the drop-down menu in the bottom right corner. Separate structures with + signs from the drop-down menu. P opy aste ? ChemDoodle®
CH3
CH3
Br
HBr
CH2
CH3
H3C
H3C
Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the electrophilic HBr by the T
electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H atom adding to the sp carbon
containing the most hydrogens, leading to the formation of the most stable carbocation (1°<2°<3°). If possible, a 1,2-shift of either a neighboring
hydride or methyl group can occur prior to the last step in order to form a more stable carbocation. In the final step of the reaction, nucleophilic
bromide adds to the carbocation to give the neutral product.
Draw curved arrows to show the movement of electrons in this step of the mechanism.
Arrow-pushing Instructions
CH3
CH3
Br-
CH3
:Br:
CH3
H3C
H3C
Submit Answer
Retry Entire Group
9 more group attempts remaining
Transcribed Image Text:CH3 CH3 Br HBr CH2 CH3 H3C H3C Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the electrophilic HBr by the T electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H atom adding to the sp carbon containing the most hydrogens, leading to the formation of the most stable carbocation (1°<2°<3°). If possible, a 1,2-shift of either a neighboring hydride or methyl group can occur prior to the last step in order to form a more stable carbocation. In the final step of the reaction, nucleophilic bromide adds to the carbocation to give the neutral product. Draw curved arrows to show the movement of electrons in this step of the mechanism. Arrow-pushing Instructions CH3 CH3 Br- CH3 :Br: CH3 H3C H3C Submit Answer Retry Entire Group 9 more group attempts remaining
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