Illustrated Glossary of Organic Chemistry Syn addition: An addition reaction in which all new bonds are formed on the same face of the reactant molecule. 1. BH3 2. HOOH, NaOH This hydroboration-oxidation reaction is a syn addition because this reaction delivers an H and OH to the same face of the alkene. + [4+2] This Diels-Alder reaction is a syn c [..]

Illustrated Glossary of Organic Chemistry Syn-periplanar: Two bonds, groups, or other molecular moieties with a 0o dihedral angle (i.e., lying in the same plane and pointing in the same direction). Sawhorse projection    Newman projection In the syn-eclipsed conformation of butane the methyl groups have a syn-periplanar relationship. Verify with a [..]

Illustrated Glossary of Organic Chemistry Talose: An aldohexose monosaccharide having the molecular structure shown below. Molecular Structure of (D)-(+)-Talose    Fischer projection

Illustrated Glossary of Organic Chemistry Tautomer: Any molecule in a set of constitutional isomers that are conceptually related by the shift of a hydrogen atom and one or more pi bonds. Tautomers of Acetone Keto form Enol form Tautomers of Acetamide

Illustrated Glossary of Organic Chemistry Tautomerization: The process of isomerization of one tautomer into another tautomer. Mechanism for acid-catalyzed tautomerization of acetone. Mechanism for base-catalyzed tautomerization of acetone.

Illustrated Glossary of Organic Chemistry Tert-butyl (tert-butyl group; tBu): A portion of a molecular structure which is equivalent to 2-methylpropane minus one hydrogen atom from carbon 2. Sometimes abbreviated as tBu. 2-Methylpropane Tert-butyl group    Related terms: Acetyl group, activating group, acyl group, alkanoyl group, alkoxy group, alky [..]

Illustrated Glossary of Organic Chemistry Tert-butoxide (tert-butoxide ion; tBuO-): (CH3)3CO-; the conjugate base of tert-butanol. A strong base (frequently used in E2 and enolate reactions) but a fairly poor nucleophile due to steric hindrance. Molecular structure of tert-butoxide ion. (CH3)3CO-  Na+ (CH3)3COH + Major product Minor product Sodium [..]

Illustrated Glossary of Organic Chemistry Tert-butanol (tertiary butanol, t-BuOH, tert-BuOH): The simplest tertiary alcohol, (CH3)3COH. Commonly used as a nonpolar protic solvent (ε = 11). IUPAC name 2-methylpropan-2-ol. Molecular Structure of Tert-butanol --to be added-- Lewis structure    Bond-line structure    Ball and spoke model    Space filli [..]

Illustrated Glossary of Organic Chemistry Teratogen: A substance that causes fetal abnormalities. Racemic thalidomide was administered to pregnant women for its antiemetic and sedative effects, but withdrawn from the market when it was discovered that its S enantiomer is teratogenic. (S)-Thalidomide

Illustrated Glossary of Organic Chemistry Terephthalic acid: A dicarboxylic acid consisting of a benzene ring with the carboxylic acid groups in a 1,4 (para) arrangement. IUPAC name benzene-1,4-dicarboxylic acid. The carboxylic acid monomer which is copolymerized with ethylene glycol to form the common plastic polyethylene terephthalate (PET). Mole [..]