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Problems and exercisesBimolecular Elimination

1. Why the Z isomer?

Propose a mechanism showing why the Z isomer is formed in this reaction.

Elimination of a stereoisomer of 2-bromo-3-methylpentane with NaOCH₃ in hot methanol to give (Z)-3-methyl-2-pentene

2. Kinetics

In an E2 reaction the concentration of the base is doubled. What happens to the rate?

3. The 1-bromo-4-tert-butylcyclohexanes

Why does the cis isomer eliminate HBr with KOH much faster than the trans isomer?

4. Small and bulky bases

Which alkene predominates in the E2 reaction of 2-bromo-2-methylbutane with sodium ethoxide? And with potassium tert-butoxide?

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