Quiz 1

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1. Multiple Choice and Ranking (14 pts):

Which of the following is not a common reagent that can oxidize an alcohol:

KMnO₄
alcohol dehydrogenase
H₂CrO₄
ZnCl₂
IBX
Bleach (NaOCl)

The inversion of stereochemistry for an S_N2 reaction is explained based on collision of a nucleophile to fill what acceptor orbital?

a \(\sigma\)bonding orbital
a \(\sigma*\) antibonding orbital
a \(\pi\) bonding orbital
a \(\pi*\) antibonding orbital
an empty \(p\) orbital

Which is not a property evaluated when considering 1-butanol as an advanced biofuel option?

solubility in water
boiling point
energy density
ability to be produced from renewable feedstock
compatibility with current engine technology
reactivity in an S_N2 reaction

d) Rank the following compounds in order of increasing boiling point (where 1 = lowest BP and 3 = highest BP) and briefly explain your answer.

2.

2. (6 pts) The compound shown below is the derivative of a pharmaceutical lead compound that exhibits antilipidemic activity. Identify (circle) which alcohol group has the most acidic proton, then draw the conjugate base and explain your answer.

3.

3. (8 pts) Propose a structure for the product of the following reaction and a mechanism for its formation.

4.

4. (8 pts) For each of the following mechanistic steps, show the flow of electrons using curved arrows and identify the donor and acceptor orbitals that are involved:

5.

5. (10 pts) Fill in the boxes to give the major product for each of the following reactions:

6.

(10 pts) a) Give the major product for the following reaction:

Draw the structure of the anion that is the leaving group for step 1 (above), and explain why this is a good leaving group.

Propose a structural modification from your answer in part b that would make an even better leaving group and explain why it would be a better leaving group. (this is NOT asking you to try to remember a structure we talked about in lecture, but instead to propose a new structure based on your working knowledge of organic chemistry. There are several correct answers)