Multistep reaction mechanisms Group Activity Treating (S)-2-butanol with HBr results in the following two step reaction: Step 1: CH3CH(OH)CH₂CH3 + HBr CH3CH(OH₂)CH₂CH3* + Br Step 2: CH3CH(OH₂)CH₂CH3 + Br CH3CH(Br)CH₂CH3 + H₂O Draw a mechanism for each step. Draw structures for all reactants and products, including correct stereochemistry (wedges and dashes). Show all the curved arrows in each step, and label each curved arrow according to whether it represents proton transfer, loss of a leaving group, nucleophilic attack, or carbocation rearrangement.

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Author:Steven S. Zumdahl, Susan A. Zumdahl, Donald J. DeCoste
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Multistep reaction mechanisms Group Activity
Treating (S)-2-butanol with HBr results in the following two step reaction:
Step 1: CH3CH(OH)CH₂CH3 + HBr
CH3CH(OH₂)CH₂CH3* + Br
Step 2: CH3CH(OH₂)CH₂CH3 + Br
CH3CH(Br)CH₂CH3 + H₂O
Draw a mechanism for each step. Draw structures for all reactants and products, including correct
stereochemistry (wedges and dashes). Show all the curved arrows in each step, and label each curved
arrow according to whether it represents proton transfer, loss of a leaving group, nucleophilic attack, or
carbocation rearrangement.
Transcribed Image Text:Multistep reaction mechanisms Group Activity Treating (S)-2-butanol with HBr results in the following two step reaction: Step 1: CH3CH(OH)CH₂CH3 + HBr CH3CH(OH₂)CH₂CH3* + Br Step 2: CH3CH(OH₂)CH₂CH3 + Br CH3CH(Br)CH₂CH3 + H₂O Draw a mechanism for each step. Draw structures for all reactants and products, including correct stereochemistry (wedges and dashes). Show all the curved arrows in each step, and label each curved arrow according to whether it represents proton transfer, loss of a leaving group, nucleophilic attack, or carbocation rearrangement.
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