From Gen Chem To Organic Chem
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The Pi Molecular Orbitals of Cyclobutadiene
…2. Upon warming (–80° is considered “warm” for these purposes), cyclobutadiene reacts with itself through a Diels-Alder process to give “dimeric” species. Note 3. If benzene is about 36 kcal/mol…
Read moreDiels-Alder Reaction: Kinetic and Thermodynamic Control
…in Diels-Alder reactions. Thermodynamic vs. kinetic control in the Diels-Alder cycloaddition of cyclopentadiene to 2,3-dicyano-p-benzoquinone Bott, S.G., Marchand, A.P. & Kumar, K.A. Chem. Crystallogr. 1996, 26, 281–286 DOI: 10.1007/BF01677782 Scheme…
Read moreThe Retro Diels-Alder Reaction
…Lett. 1981, 22 (15), 1393-1396 DOI: 10.1016/S0040-4039(01)90330-2 The normal Diels-Alder reaction proceeds best when the diene is electron-rich and the dienophile electron-poor. However, in certain cases, the opposite polarity is…
Read moreThe Pi Molecular Orbitals of Benzene
…lowest in energy. Here’s what the “ground floor” looks like for butadiene: The highest energy level (the “penthouse” of our building) has (n–1) nodes. We saw that for butadiene (n=4)…
Read moreWhy Are Endo vs Exo Products Favored in the Diels-Alder Reaction?
…Acids on endo:exo selectivity. Endo and Exo transition states in the Diels-Alder reaction William C. Herndon and Lowell H. Hall Tetrahedron Lett. 1967, 8 (32), 3095-3100 DOI: 10.1016/S0040-4039(00)90922-5 An very…
Read moreReactions of Diazonium Salts: Sandmeyer and Related Reactions
…cuprous acetylide, and instead obtained chlorobenzene. Ueber die Ersetzung der Amid‐gruppe durch Chlor, Brom und Cyan in den aromatischen Substanzen Traugott Sandmeyer Ber. 1884 17 (2), 2650-2653 DOI: 10.1002/cber.188401702202 Sandmeyer…
Read moreIntroduction to Peptide Synthesis
…“peptide bond” is an amide linkage (see Amides: Properties. Synthesis, and Nomenclature) that connects two amino acids, as in the “dipeptides” L-phenylalanyl-L-valine (below left) and L-leucyl-L-alanine (below right): 2. The…
Read moreFormation of enamines from ketones/aldehydes and secondary amines
…flashcards, sign up here for only 30 cents/ day! Real-Life Examples: Org. Synth. 1968, 48, 56 DOI Link: 10.15227/orgsyn.048.0056 Click to Flip Org. Synth. 1961, 41, 65 DOI Link: 10.15227/orgsyn.041.0065…
Read moreThe Strecker Synthesis of Amino Acids
…Flip Org. Synth. 1944, 24, 9 DOI Link: 10.15227/orgsyn.024.0009 Click to Flip Org. Synth. 1953, 33, 7 DOI Link: 10.15227/orgsyn.033.0007 Click to Flip (Advanced) References and Further Reading This is…
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