You react the following molecule with a strong bulky base (like KOtBu), and you know that the Cl atoms are all susceptible to elimination under these conditions. You also know that there are two competing mechanisms by which this reaction can occur: Mechanism 1: The double bond can form in several steps, the slowest of which is unimolecular. In this mechanism, the Cl atom leaves first, and the base removes a beta hydrogen in a subsequent step. Highlight in blue the Cl atom that would be eliminated quickest if the reaction went by this type of mechanism. Mechanism 2: The double bond can form in a concerted bimolecular step, removing the Cl atom and a beta hydrogen in the process. Highlight in red the Cl atom that would be eliminated quickest if the reaction went by this type of mechanism. If you would highlight the same Cl atom for both mechanisms, highlight it in green instead. Cl Cl CI G

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Chapter1: Chemical Foundations
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You react the following molecule with a strong bulky base (like KOtBu), and you know that the Cl atoms are all susceptible to elimination under these
conditions. You also know that there are two competing mechanisms by which this reaction can occur:
Mechanism 1: The double bond can form in several steps, the slowest of which is unimolecular. In this mechanism, the Cl atom leaves first, and the base
removes a beta hydrogen in a subsequent step. Highlight in blue the Cl atom that would be eliminated quickest if the reaction went by this type of mechanism.
Mechanism 2: The double bond can form in a concerted bimolecular step, removing the Cl atom and a beta hydrogen in the process. Highlight in red the Cl
atom that would be eliminated quickest if the reaction went by this type of mechanism.
If you would highlight the same Cl atom for both mechanisms, highlight it in green instead.
Cl
Cl
Cl
B
G
Transcribed Image Text:You react the following molecule with a strong bulky base (like KOtBu), and you know that the Cl atoms are all susceptible to elimination under these conditions. You also know that there are two competing mechanisms by which this reaction can occur: Mechanism 1: The double bond can form in several steps, the slowest of which is unimolecular. In this mechanism, the Cl atom leaves first, and the base removes a beta hydrogen in a subsequent step. Highlight in blue the Cl atom that would be eliminated quickest if the reaction went by this type of mechanism. Mechanism 2: The double bond can form in a concerted bimolecular step, removing the Cl atom and a beta hydrogen in the process. Highlight in red the Cl atom that would be eliminated quickest if the reaction went by this type of mechanism. If you would highlight the same Cl atom for both mechanisms, highlight it in green instead. Cl Cl Cl B G
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