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1-Bromobicyclo[2.2.2]octane does not undergo an E2

Chapter 8, Problem 8.72

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QUESTION:

1-Bromobicyclo[2.2.2]octane does not undergo an E2 reaction when treated with a strong base. Explain why not.

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QUESTION:

1-Bromobicyclo[2.2.2]octane does not undergo an E2 reaction when treated with a strong base. Explain why not.

ANSWER:

Step 1 of 2

If this compound undergoes an E2 reaction, a bridgehead alkene would form (an alkene between the bridgehead C atom and a branch C atom).

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