Project 2

Project Overview

Laboratory work for Project 2 will be completed in pairs. Each assignment (e.g., workshops, quizzes, reports) must be completed individually.

Organic chemists often try to synthesize a complex molecule from simpler starting materials. This task generally requires sequential reaction steps in which the product of one reaction serves as the reactant for the next step in the sequence. The objective of this project is to prepare the target compound (Figure 1) by a two-step reaction sequence.

Figure 1. Target compound for Project 2

The target compound is an example of a biphenyl, which consists of two aromatic rings bonded directly to each other. The development of synthetic methods for the production of biphenyls is important because many of these compounds exhibit important biological activity. For example, polysperlignan A (1) has demonstrated anti-neurodegenerative activity. Bicyclol (2) is an anti-hepatotoxic drug, and Merck sells the antihypertensive drug Losartan (10) (Figure 2).

Figure 2. Some examples of biologically important biphenyls

Project 2 is intended to cultivate your skill and independence in designing and implementing a reaction sequence based on previously reported data. This is the basic work of a synthetic organic chemist. In the Project 2 scenario, you are given “literature precedent” for your reactions in the form of journal-style experimental descriptions as well as some relevant general theoretical background. In Part A, you are expected to perform the reaction reported in the procedure at a different scale (i.e. with different quantities of materials). In Part B, you will use the literature procedure as a template for performing the same type of reaction, but you will choose substrates different than those in the reported procedure.

Learning Objectives

At the end of this project, you should know how to:

• Plan and complete sequential chemical reactions based on literature precedent

• Adjust the scale of a chemical reaction from literature precedent

• Calculate the overall yield of a reaction sequence

• Determine the substitution pattern of an aromatic ring from spectroscopic data

• Carry out an aromatic substitution reaction and a palladium-catalyzed cross-coupling reaction.

Project 2 Score Distribution