Chapter 4 Chem 30A Week 5 Warm up exercise Identify the acidic and basic sites on each of the molecules below O NH2 O O Group problems 1 Imidazole acts as a base in water a Write a balanced equation for that reaction HN N imidazole b Explain why one nitrogen in imidazole is favored over the other for protonation c Draw resonance forms of protonated imidazole Chem 30A Spring 2006 Chapter 4 2 How many stereogenic carbons does Penicillin V have What are there configurations O O NH H S H N O O OH Penicillin V 3 Use the pKa s listed for the following questions HO phenol pKa 10 OH methanol pKa 16 O acetone pKa 18 acetylene pKa 25 a Why is phenol more acidic than methanol and acetone Chem 30A Spring 2006 Chapter 4 b For the following equations does the equilibrium lie to the right or left H O OH OH O O HO c Can acetone protonate acetylide anion Write the reaction label the acid base conj acid and conj base Chem 30A Spring 2006
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