MULTISTEP SYNTHESIS PROJECTS

Introduction

Up to this point in organic chemistry laboratory, all of the synthetic experiments you have done have been one or two steps with no isolation of intermediate products. In the real world organic chemists often need more than one step to synthesize a target molecule from available starting materials. For your last experiment you will perform a multistep synthesis, and seven are shown below. The experimental details are deliberately a little bare: you will need to think about what to do at certain key points. You will also need to decide how to characterize your intermediate products and determine whether they need purification prior to the next step. It will be helpful for you to gather literature values on your products prior to coming to lab. Also, you need to write out the mechanisms of the reactions.


Synthesis 1: Wittig Reaction and Diels Alder Synthesis

[Speed, T.J..; McIntyre, J.P.; Thamattoor, D.M. J. Chem. Educ. 2004, 81, 1355-6]

Synthesis 2: Chalcone Derivative

[Moloney, G. P. J. Chem. Educ. 1990, 67, 617
Dixon, C. E.; Pyne, S. G. J. Chem. Educ 1992, 69, 1032.]

Synthesis 3: A Synthetic Competition

[Stradling, S.S.; Gage, C.L. J. Chem. Ed. 1985, 62, 1117-7]

Synthesis 4: Multistep Synthesis of 4-Nitro-1-ethynylbenzene Involving Palladium Catalysis, Acetal Hydrolysis, and Oxidative Decarbonylation

[Goodwin, T. E.; Hurst, E. M.; Ross, A. S. J. Chem. Educ. 1999, 76, 74-75]

Synthesis 5: Synthesis of the dye para red from Aniline

[Mohrig, J.R.; Morrill, T.C.; Hammond, C.N.; Neckers, D.C. Experimental Organic Chemistry; Freeman: New York, NY, 1997; pp 456-67]

Synthesis 6: Nylon

Synthesis 7: Benzyne Formation and a Diels-Alder Reaction

[Pavia, D.L.; Lampman, G.M.; Kriz, G.S. Organic Laboratory Techniques; Saunders: New York, NY, 1995; pp 286-289, 293-296, 429-434]