Why is melphalan a good cancer drug?

Would you expect the following bases to favor E1 or E2 elimination?

(d) H₂O

Paying close attention to the stereochemical outcome, predict the product of these elimination reactions.

(c)

Indicate the type of catalysis that is occurring in the slow step in each of the following reaction sequences:

a.

Indicate the type of catalysis that is occurring in the slow step in each of the following reaction sequences:

b.

Indicate which species in each pair gives a higher substitution-product-to-elimination-product ratio when it reacts with isopropyl bromide:

c. Cl⁻ or Br⁻

The following three nitrogen mustards were studied for possible clinical use. One is now used clinically, one was found to be too unreactive, and one was found to be too insoluble in water to be injected intravenously. Which is which? (Hint: Draw resonance contributors.)

Finish Solved Problem 7-3 by showing how the rearranged carbocations give the four products shown in the problem. Be careful when using curved arrows to show ­deprotonation and/or nucleophilic attack by the solvent. The curved arrows always show ­movement of electrons, not movement of protons or other species.

Give the substitution and elimination products you would expect from the following reactions.

c. 1-bromo-2-methylcyclohexane + silver nitrate in water (AgNO₃ forces ionization)