Organic Chemistry Cheat Sheet, Cheat Sheet of Organic Chemistry

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John’s Organic Chemistry Cheat Sheet The product of a non-chemist’s decade long collaboration with chemists Sources: - Wikepedia encyclopedia of organic chemistry: http://en.wikipedia.org/wiki/Organic_chemistry - Organic Chemistry, textbook by Seyhan Ege - ChemHeritage glossary (limited list but includes figures in many cases): http://www.chemheritage.org/EducationalServices/pharm/glossary/glossary.htm - “ChemCool” chemistry dictionary: http://www.chemicool.com/dictionary.html - Virtual text of organic chemistry: http://www.cem.msu.edu/~reusch/VirtualText/intro1.htm - “About” organic chemistry (includes: chemical structures archive, alkane nomenclature and numbering, and functional groups subpages): http://chemistry.about.com/od/organicchemistry/ - “Chemical Forums” chemical structures: http://www.chemicalforums.com/index.php?page=molecules - Clackamas community college chemistry 106 lessons online (includes diagrams of sigma and pi bonds) http://dl.clackamas.cc.or.us/ch106-02/ A Abstraction Synonymous with removal Acyl / Acyl group Acetyl/Acetyl group: Acid Specie that can donate a proton (Bronsted-Lowry definition). Specie that can accept a spare electron (Lewis definition). Activation Group on ring that makes it easier to introduce a second substituent = activation Alcohol R-OH Aldehyde (doubly bonded O in middle of molecule = ketone) Allyl Group CH2=CHCH2- Aliphatic Definition 1: “Acyclic or cyclic, saturated or unsaturated carbon compounds, excluding aromatic compounds” (In other words, NOT aromatic). Definition 2 (not exactly equivalent!): “Organic molecules joined together in straight or branched chains” Alkane Carbon with tetrahedral bonds (single, covalent) to other carbons, or to hydrogen. C-C bond length ~ 1.54A. Distance between 2nd nearest C’s (along the spine of the alkane ~2.5A) Alkene An alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon to carbon double bond. C=C bond length ~ 1.33A Alkyne A hydrocarbon containing at least one carbon to carbon triple bond. CΞC bond length ~ 1.2A Alkyl group Alkane minus one hydrogen/proton (generally attached to something else) Amide: Amine group Nitrogen with three bonds plus unbonded electron pair Diacyl peroxide (used as a Si radical initiator in hydrosilylation) DMSO (CH3)2SO Dimethylsulfoxide E ee Enantiomeric excess = (R-S)/(R+S) = excess of one enantiomer divided by concentration of both enantiomers (In this context S = left handed (from Latin sinister), R = right handed. This R not to be confused with broader use of R in organic chemistry to denote any possible "appended organic molecule segment") Electrolyte Plus and minus ions in solution Enantiomers Mirror image molecules (i.e. complementary molecules of opposite chirality) -ene (suffix) an organic compound with a double bond between carbon atoms Enediynes Molecule with carbon chain containing two triple bonds separated by a double bond Ester Ether Ethyl / Ethyl group A molecule containing two carbon atoms (ethane minus one hydrogen/proton) eV 1 eV = 23.0627 kcal/mol Exogenous “Originating externally. In the context of metalloprotein ligands, exogenous describes ligands added from an external source, such as CO or O2.” F Facile substitution Easy substitution Ferrocene or in terms of bonding: Furan Five member “unsaturated” ring with oxygen in one position G Grignard Organometallic reagents prepared by deprotonating an organic compound using a strong base Nucleophile or by reaction of organic halides with alkaline metals H Hydroxyl group -(OH) Homolytic Breaking a bond such that each of the atoms gets one of the electrons Cleavage Homolysis Same as Homolytic Cleavage, above K Ketone That is, molecule with central carbonyl group. (Doubly bonded O at END of molecule = aldehyde) kilocalorie 1 kilocalorie = 2.61144768 × 1022 electron volts = 4.184 joule kcal/mol 1 kcal/mol = 0.04336 eV (thus 1 eV = 23.0627 kcal/mol) L Labile As in “kinetically labile”: Constantly undergoing change or something that is likely to undergo change Mercaptin “A traditional term abandoned by IUPAC, synonymous with thiols.” Methyl A molecule containing one carbon atom N Napthalene Nitrile group -(C≡N) Nucleophile literally nucleus lover = a reagent forms a chemical bond to its reaction partner (the electrophile) by donating both bonding electrons Nucleophilic: Nucleophile becomes attracted to a full or partial positive charge on an element and displaces the substitution group it is bonded to. Nucleophilic Attack See Nucleophile O Oxidation Loss of electron OCP Open circuit potential Olefin An alkene, olefin, or olefine is an unsaturated chemical compound containing at least one carbon to carbon double bond Reduction S Salt Saturated Gain of an electron Ionic compounds that can be formed by replacing one or more of the hydrogen ions of an acid with another positive ion. Carbon chained together with single bonds (with other carbon bonds being to hydrogen atoms) = carbon chain loaded with maximum number of possible hydrogen atoms (i.e. “saturated”) Sigma bond a sigma bond is a valence bond that is symmetrical around the imaginary line between the bonded atoms. Most single bonds are sigma bonds Steric hindrance When a chemical reaction is hindered by unacceptable overlap of atoms, electron orbitals, or the formation of unfavorable bond lengths or angles (i.e. outcome of reaction is at least partially dictated by actual fit of atoms) Styrene T TEMPO 2,2,6,6-Tetramethylpiperidine 1-oxyl (organic radical on O site) Thiol / Thiol group -(S-H) Thiophene Toluene THF Tetrahydrofuran – solvent used in rinsing off organic layers (completely hydrogen saturated version of furan) U Unsaturated Opposite of saturated = carbon compound with less than maximum possible number of hydrogen’s implying some carbon atoms chained together with double or single bonds. V “vide infra” Latin for “see below” “vide supra” Latin for “See earlier” or “look above this page" Vinyl compound Containing a vinyl group: Y -yne (suffix) an organic compound containing a triple bond between carbon atoms Z Zwitterion A chemical compound that is electrically neutral but carries formal positive and negative charges on different (generally separated) atoms (i.e. what a physicist would just call a polar molecule!)