ASSIGNMENT
1. What is the hybridization of the indicated atoms in Ambien (sedative used in the treatment of insomnia). Make a small table of hybridized and any unhybridized atomic orbitals for the atoms and indicate how they are used.
2. A. Draw the minor resonance contributor(s) to identify all sites of low electron density
(+) in the following compound.
B. Draw the minor resonance contributor(s) to identify all sites of low electron density
(–) in the following compound.
3. Draw the most stable chair conformation of glucose.
4. Ascorbic acid (vitamin C) pKa = 4.2 does not contain a carboxylic acid group, but is
fairly acidic. Identify the acidic proton and explain the choice using resonance structures.
5. L–dopa is used in the treatment of Parkinson’s disease. Identify the four most acidic
protons and arrange them in order of increasing acidity.
6. Coumarins are a class of natural products produced by plants and animals. It has a wide
variety of applications in cosmetics, food industry and fluorescent laser dyes. In the
1HNMR spectrum of coumarin derivate shown below, the two signals farthest downfield
are at 7.38 and 8.42 pm. Identify the two protons that most likely give rise to these
signals and justify your answer using resonance structures.
