Organic Chemistry: 1,2,4,6,8,9,5,10

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Bachelors Science Flashcards on Organic Chemistry: 1,2,4,6,8,9,5,10, created by iPad Air on 12/17/2015.

Resource summary

Question Answer
Functional groups Structural characteristics can make molecules function similarly, common partnering of atoms that are agents of reactivity
Alkane group Carbon-carbon single bonds, often have hydrogen bonded to a carbon, simplest and least reactive compound
Heteroatom Atoms other than carbon or hydrogen, N,O,Halogens,S
Alkene group Carbon-carbon double bonds, stronger than single but weaker than triple, able to function as bases or nucleophiles
Alkyne group Carbon-carbon triple bond, stronger than double bond, linear geometry, able to function as bases or nucleophiles
Arene group Carbon-carbon ring with alternating double and single bonds
Halide group Elements are abbreviated with an X, include a carbon-halogen bond, F,Cl,Br,I
Alcohol group Carbon-hydroxide bond
Ether group Carbon-oxygen-carbon bond
Amine group Carbon-nitrogen group, primary, secondary, tertiary
Nitrile group Carbon-nitrogen triple bond, cyanide anion or CN- with active organic species
Nitro group Formal charges, nitrogen with four bonds and no lone pairs with +1 charge, oxygen with one bond and three lone pairs with -1 charge, free to resonate so that negative charge can be shared between two oxygen atoms with +1 charge on nitrogen
Sulfide/thioether group Sulfur equivalent of an ether, carbon-sulfur-carbon bond
Thiol group Sulfur equivalent of alcohol, carbon-sulfur-hydrogen bond
Carbonyl group Carbon-oxygen double bond, contains subgroup of molecules
Aldehyde group Carbon-carbonyl-hydrogen
Ketone group Carbon-carbonyl-carbon
Carboxylic acid group Carbon-carbonyl-hydroxide
Ester group Carbon-carbonyl-oxygen-carbon
Amide group Carbon-carbonyl-nitrogen
Acid chloride group Carbon-carbonyl-chlorine
Acid anhydride group Two carboxylic acids minus a water molecule
Imine group Nitrogen equivalent of carbonyl, carbon-nitrogen-double bond
Epoxide group Cyclic ether, carbon-oxygen-carbon
Phenol group Arene ring with hydroxide attached, specifically benzene
Aniline group Arene with amine attached
Hydrocarbons Compounds composed of only carbon and hydrogen
Alkanes/saturated hydrocarbons Hydrocarbons containing only single bonds, lack pi bonds
Straight-chain n-alkanes Simplest structure of alkanes, homologs of H-(CH2)n-H
Straight-chain n-alkanes molecular formula CnH2n+2
Isomers Compounds that have the same molecular formula but differ in physical and/or chemical properties
Constitutional isomers Isomers that differ in connectivity
C1 prefix and condensed structure Meth, CH4
C2 prefix and condensed structure Eth, CH3CH3
C3 prefix and condensed structure Prop, CH3CH2CH3
C4 prefix and condensed structure But, CH3CH2CH2CH3
C5 prefix and condensed structure Pent, CH3CH2CH2CH2CH3
C6 prefix and condensed structure Hex, CH3CH2CH2CH2CH2CH3
C7 prefix and condensed structure Hept, CH3(CH2)5CH3
C8 prefix and condensed structure Oct, CH3(CH2)6CH3
C9 prefix and condensed structure Non, CH3(CH2)7CH3
C10 prefix and condensed structure Dec, CH3(CH2)8CH3
C11 prefix and condensed structure Unde, CH3(CH2)9CH3
C12 prefix and condensed structure Dodec, CH3(CH2)10CH3
Alkyl group Alkane from which a single hydrogen has been removed, changes from standalone alkane to a substituent of a larger molecule
-R Generic alkyl group
Iso group CH connected to 2 methyl groups
Neo group Central carbon surrounded by multiple methyl groups
Primary carbon 1˚ bonded to one C
Secondary carbon 2˚ bonded to two C
Tertiary carbon 3˚ bonded to three C
Quaternary carbon 4˚ bonded to four C
-ium Denotes positive charge
-ide Denotes negative charge
sp3 hybridized atoms 4 electron dense areas, no double bonded C,O,Halogens
Nuclei Positively charged, define atomic positions as cartesian coordinates
Electron cloud/orbital Region of space that can be occuped by an electron, negatively charged, defines molecule size and shape, 1s orbital has low energy
Distribution of charge Reveals molecule's chemical and physical properties
Electrostatic potential map Represents molecular charge distribution, illustration of 3D electron density surface around ball and stick model or electron cloud, warm colors represent high electron density, cool colors represent low electron density
Types of molecular models Wireframe, ball and stick, space filling
Electrostatic potential energy Coulombic energy that a point positive charge feels as it passes over electron cloud
Coulombic energy High electron dense atoms are electron rich and have low coulombic energy
Valency Number of bonds an element forms, carbon is tetravalent, nitrogen is trivalent, oxygen is divalent, hydrogen and halogens are monovalent
Lewis structures Count valence electrons on columns of periodic table, connect all bonds
Electronegativity Ability of an atom to attract electrons, <0.5 is equal or covalent, 0.5-1.7 is unqual or polar covalent, >1.7 does not share and is ionic - the result of the force of attraction between two oppositely charged ions, atom with higher electronegativity is sigma- or electron rich, atom with lower electronegativity is sigma+ or electron poor, greater electronegative pair is more ionic
Induction WIthdrawal of electrons toward oxygen, causes partial positive and partial negative charges
Single bonds sp3 hybridized, one sigma bond, longest, weakest, steric number 4
Double bonds sp2 hybridized, one sigma bond, one pi bond, shorter, weaker, steric number 3
Triple bonds sp hybridized, one sigma bond, two pi bonds (overlapping p orbitals), shortest, strongest, steric number 2
Steric number Total pi bonds plus lone pairs, number of electron pairs repelling each other whether bonding or nonbonding
Intermolecular forces Attractive forces between individual molecules, electrostatic, can be dipole dipole interaction or hydrogen bonding or fleeting dipole diple interaction, higher boiling point is less branched
IUPAC nomeclature Choose longest carbon chain with most substituents
Straight chain substituents Receive generic alkyl group names
Complex substituents Treat as a miniparent, put everything in parentheses, longest carbon chain numbered starting from parent chain unless you can make substituents smaller numbers, numbered substituent followed by mini parent, EX: (2-methylbutyl), alphabetical substituents should come first
Bicyclic Two fused rings, label carbons from bridgehead along longest path to shortest, EX. 6-methylbicyclo[3.2.1]octane
Conformation Variety of possible 3D shapes adopted from rotation about carbon-carbon single bonds
Dihedral/torsional angle Angle of bonds in a conformation anywhere from 0˚-180˚
Staggered conformation Lowest energy
Eclipsed conformation Highest energy
Anti conformation Confirmation with lowest energy
Gauche interaction Type of steric interaction, different from torsional strain, when two electron clouds are repelling each other/trying to occupy the same region of space, conformations with least gauche interactions are lowest in energy
Homolytic bond cleavage Generates uncharged radicals, uses fish hook arrows, energy required to break a covalent bond is bond dissociation energy
Heterolytic bond cleavage Generates charged ions, uses a two headed arrow
Isopropyl (1-methylethyl)
sec-Butyl (1-methylpropyl)
Isobutyl (2-methylpropyl)
tert-Butyl (1,1-dimethylethyl)
Isopentyl/isoamyl (3-methylbutyl)
Neopentyl (2,2-dimethylpropyl)
Ethane conformation 12 kJ/mol diference, all staggered are degenerate, all eclipsed are degenerate, each eclipsing hydrogen pair is 4 kJ/mol
Torsional strain Difference in energy between staggered and eclipsed conformations
Propane conformations 14 kJ/mol diference, all staggered are degenerate, all eclipsed are degenerate, each eclipsing hydrogen pair is 4 kJ/mol, hydrogen-methyl group is 6 kJ/mol
Butane conformations Not degenerate, eclipsed confomation at dihedral angle 0˚ is higher in energy, staggered conformation at dihedral angle 180˚ is lower in energy, eclipsing methyl groups cost 11 kJ/mol
Cyclohexane conformations Both conformations possess very little angle strain (close to 109.5˚), chair conformation has no torsional strain, boat conformation has two torsional strains from flagpole interactions, boat conformation can alleviate torsional strain by forming a twist boat
Exothermic Negative heat of reaction dH˚, decreased in energy/gave energy to surroundings, starting materials to products
Endothermic Positive heat of reaction dH˚, increased in energy/gained energy from surroundings, products to starting materials
Kinetics Dependent on rate of reaction
Thermodynamics Dependent on equilibrium concentrations of reactants and products
Ionic/polar reactions Involve ions as reactants,products,or most commonly intermediates, one reactant has a site of high electron density and other reactant has a site of low electron density
Nucleophile Electron rich center, has ability to react with a positive or partial positive charge, capable of donating a pair of electrons
Electrophile Electron deficient center, has ability to react with negative or partial negative charged, capable of accepting a pair of electrons
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