Destroyer Road Map 3 Help

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busupshot83

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On the Destroyer Road Map 3 (pg. 105 of the Organic section), if you begin at START, and go RIGHT, you will see cyclopentane with a Br and CH3 coming off one of its top carbon. The arrows to the top and bottom of this structure are both the same reaction (dehydrohalogenation or beta-elimination), correct? Just wanted to make sure.

Also, in dehydrohalogenation, are two bases needed? I am asking because the Destroyer shows two bases, but my Organic Chemistry II professor's notes shows one. I'm thinking that my professor's notes assumes that the reaction occurs in an aqueous base with a large supply of bases present.
 
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