Tautomerization Practice Problems
Draw the tautomeric forms of adenine and thymine with aromatic hydroxy and amino groups.
A student tried to synthesize the octapeptide Thr-Pro-Glu-His-Tyr-Asn-Ile-Gln in the lab and got a yield of 85% for the addition of each amino acid to the chain. What is the overall yield for the synthesis of Thr-Pro-Glu-His-Tyr-Asn-Ile-Gln?
Draw the structure of the enol tautomers of the following compound and identify the more stable one.
The following reaction shows an acid-catalyzed rearrangement of a β,γ-unsaturated carbonyl compound to a more stable α,β-unsaturated compound. Draw a mechanism for this rearrangement.
Propose the acid-catalyzed mechanism of interconversion of (3R)- and (3S)-3,4-dimethylhexan-2-one.