Integrated SequencePhysics Chemistry Organic Biology

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Module 9 in the Syllabus

Reaction of Alcohols with Phosphorus Tribromide
Mechanisms and explanations from the Organic Mechanisms Pocketbook

The Wittig Reaction
Mechanisms and explanations from the Organic Mechanisms Pocketbook

Reactions of Organic Phosphorus Compounds Images
Image gallery for study with links to larger teaching JPEGs for classroom presentation

Question Drill for Reactions of Organic Phosphorus Compounds
Conceptual Vocabulary Self-Test

Basic Terms Crossword Puzzle

Basic Puzzle Solution

Conceptual Vocabulary
PhosphorusPhosphorus is the chemical element that has the symbol P and atomic number 15.
Phosphodiester bondA phosphodiester bond is a group of strong covalent bonds between the phosphorus atom in a phosphate group and two other molecules over two ester bonds. Such bonds make up the backbone of DNA.
OrganophosphateAn organophosphate is the general name for esters of phosphoric acid.
PhosphonateA phosphonate is a phosphonic acid, its conjugate base, or the ester of a phosphonic acid.
PhosphinePhosphine is the common name for phosphorus hydride, also known by the IUPAC name phosphane and, occasionally, phosphamine.
Phosphonic acidWithin organic chemistry, a phosphonic acid contains an organic portion bound to a phosphorus which is singly bonded to two hydroxyl oxygens and doubly bonded to a third oxygen.
Phosphorus tribromidePhosphorus tribromide is widely used in the laboratory for the conversion of alcohols to alkyl bromides.
PhosphoniumThe phosphonium cation is a positively charged polyatomic ion in which a phosphorus atom is bound to four hydrogens.
TriphenylphosphineTriphenylphosphine is a common organophosphorus compound in which a single phosphorus is bound to three phenyl groups.
Phosphonium saltAlkyltriphenyl-phosphonium salts are widely used for the preparation of Wittig reagents for the Wittig reaction.
Phosphite esterPhosphite esters are esters of phosphorous acid in which all three oxygens form ester linkages with carbon.
Wittig reactionThe Wittig reaction is a chemical reaction of an aldehyde or ketone with a triphenyl phosphonium ylide to give an alkene and triphenylphosphine oxide.
BINAPBINAP is an acronym for an important chiral ligand widely used in asymmetric synthesis, which consists of two naphthyl groups linked by a single bond with diphenylphosphino groups at the end of each naphthyl group.
Phosphoryl chloridePhosphoryl chloride is used to make phosphate esters. It contains phosphorus in a double bond with oxygen and singly bonded to three chlorine atoms.
Advanced terms that may appear in context in MCAT passages
Appel reactionThe Appel reaction is an organic reaction that converts an alcohol into an alkyl chloride using triphenylphosphine and carbon tetrachloride.
Horner-Wadsworth-Emmons reactionThe Horner-Wadsworth-Emmons reaction is the chemical reaction of stabilized phosphonate carbanions with aldehydes or ketones to produce predominantly E-alkenes.
Perkow reactionThe Perkow reaction is an organic reaction in which a trialkyl phosphite ester reacts with a haloketone to form a vinyl phosphonate and an alkyl halide.
Staudinger reactionThe Staudinger reaction is a chemical reaction in which the combination of an azide with a phosphine or phosphite produces an iminophosphorane intermediate. This reaction is the first step in a mild method of reducing an azide to an amine.

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