Final Post: New Organic Multistep Synthesis

Hello all,

As the summer comes to an end, I am pleased to report that the new multi-step synthesis for the second semester organic chemistry lab was a complete success with 100% of our students completing the four-step procedure and synthesizing a p-terphenyl derivative. The new procedure will be broken up into three lab periods, and for those of you taking the Organic Chemistry 2 lab in the fall, prepare for an exciting, challenging and ultimately rewarding experience as we continue to advance the W&M chemistry curriculum.

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Update: Step 3 of the Multistep Synthesis; Isomerization

Hello all,

Isomerization (or rearrangements) is the process by which a molecule is transformed into an isomer of itself. That is, a molecule that undergoes isomerization will have all the same atoms as before but the way they are arranged will differ. Isomerizations can happen spontaneously when one isomer is more stable than the other. The energetically less-favorable isomer can still be generated by a catalyst. This sort of catalyzed isomerization reaction happens very regularly in the human body.

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Update: Step 2 of the Multistep Synthesis; The Diels-Alder Reaction

Hello all,

Like the Wittig Reaction, the Diels-Alder Reaction is used extensively in Organic Synthesis to generate carbon-carbon bonds. This particular reaction, first described in 1928 by Nobel laureates Otto Diels and Kurt Alder, involves the [4+2] cycloaddition of a cis conjugated diene, and a dienophile (which can be an alkene or alkyne). The reaction produces cyclohexenes and it is very easy to control the steriochemical properties of the formed product.

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Organic Multi-step Synthesis: Step 1 – The Wittig Reaction

Many reactions in chemistry form carbon-carbon bonds. The Wittig Reaction discovered in 1954 by Nobel laureate George Wittig, is one of the most reliable ways of forming new carbon-carbon double bonds. Because it is so reliable, it is commonly used in organic synthesis to prepare alkenes. With an aldehyde or ketone as a starting reagent in the presence of an organophosphorus ylide (a compound containing a charged phosphorus atom that is adjacent to an oppositely charged organic atom) an organophosphine oxide and an alkene will be formed.

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Abstract: The Multistep Synthesis of a p-Terphenyl Derivative

Hello all,

My name is Timothy Beck and I am a Junior majoring in Health Science and Biochemistry. My project seeks to achieve a new multi-step synthesis of a compound in the class of drugs called Terphenyls.

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