When is treated with a strong base, how many different alkenes (constitutional isomers) can be formed as major products via elimination?
A
B
C
D
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1
Identify the structure of 2-bromooctane: it is an eight-carbon chain with a bromine substituent on the second carbon.
Recall that E2 elimination requires a strong base to abstract a proton from a β-carbon (a carbon adjacent to the carbon bearing the leaving group), leading to the formation of a double bond between the α-carbon (carbon with bromine) and the β-carbon.
Determine all possible β-carbons adjacent to the carbon bearing the bromine (carbon 2). In this case, the β-carbons are carbon 1 and carbon 3.
For each β-carbon, consider the different types of hydrogens (if any) that can be abstracted to form alkenes. Remember that elimination can occur on either side of the bromine-bearing carbon, and the position of the double bond will differ accordingly.
Draw all possible alkenes formed by elimination at each β-carbon, then count the number of unique constitutional isomers (different connectivity of atoms) that result from these eliminations.