H3C CH3 Arrow-pushing Instructions 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 electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H atom adding to the sp² 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. NOC XT Submit Answer HBr CH3 H-Br Br Retry Entire Group CH3 H3C H 8 more group attempts remaining CH3

Pushing Electrons
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Author:Weeks, Daniel P.
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Chapter3: Mechanisms
Section: Chapter Questions
Problem 16EQ
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Please indicate if the arrows represent the movement of one electron or a pair of electrons!

H3C
H3C
CH3
Submit Answer
HBr
Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the
hydrogen of the electrophilic HBr by the electrons of the double bond to give a carbocation. This step
follows Markovnikov's rule with the electrophilic H atom adding to the sp2 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
AOC XT
CH3 H-Br
محمد
Retry Entire Group
CH3
H3C
H
8 more group attempts remaining
CH3
Br
Transcribed Image Text:H3C H3C CH3 Submit Answer HBr Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the electrophilic HBr by the electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H atom adding to the sp2 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 AOC XT CH3 H-Br محمد Retry Entire Group CH3 H3C H 8 more group attempts remaining CH3 Br
H3C
H3C
07
H3C
H3C
CH3
CH₂
CH3
C→XT
HBr
CH3
Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the
hydrogen of the electrophilic HBr by the electrons of the double bond to give a carbocation. This step
follows Markovnikov's rule with the electrophilic H atom adding to the sp2 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
Br
H3C
CH₂ H-Br
CH3
CH3
H3C.
H3C
CH3
CH3
Br
Transcribed Image Text:H3C H3C 07 H3C H3C CH3 CH₂ CH3 C→XT HBr CH3 Electrophilic addition of HBr to alkenes yields a bromoalkane. The reaction begins with an attack on the hydrogen of the electrophilic HBr by the electrons of the double bond to give a carbocation. This step follows Markovnikov's rule with the electrophilic H atom adding to the sp2 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 Br H3C CH₂ H-Br CH3 CH3 H3C. H3C CH3 CH3 Br
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