39 Cards in this Set
Front | Back |
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Bronsted Acid
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proton donor
potential acids: anything with an H
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Bronsted Base
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proton acceptor
potential species- any species with a LONE PAIR
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Lewis Acid
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electron pair acceptor
example: H+ ion
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How to create an enantiomer
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switch 2 at EVERY chirality center
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How to create a diastereomer
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switch 2 at only ONE chirality center
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Formal charge
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(# of valence e-) - (nonbonded e- + # of bonds)
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Predicting anion stability
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1. more stable with resonance
2. larger surface area of atom
3. higher electronegativity
4. hybridization- more S character, more stable
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Alkanes
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common: "meth, eth, prop, etc" + "ane"
IUPAC: common name of longest chain, name and number substituents as alkyl groups
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Alkyl groups
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Alkane prefix + "yl"
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Cycloalkanes
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put "cyclo" in front of the IUPAC name for the corresponding alkane;
substituents are named just like alkanes
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If a ring has two substituents, what is special about the naming?
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the name is preceded by either "cis" or "trans"
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Alkyl Halide
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Common: common alkyl group name followed by the halide name (chlorine-chloride)
IUPAC: halogens named as substituents on main chain; substituents named by dropping ine from element and adding o (bromine-bromo)
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Alcohols
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Common: specify the alkyl group, followed by "alcohol"
IUPAC: longest chain that contains OH, number so OH gets lowest carbon; name substituents like alkanes but drop e and add ol; number of OH group just prior to alkane name
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Ether
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Common: specify two alkyl groups followed by "ether" (if both alkyl groups are the same, put prefix "di" in front of alkyl group name
IUPAC: longest chain attached to oxygen = main chain; other group along with the oxygen is like substituent called "alkoxy group" (ex: O with 2 carbons = …
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Amine
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Common: specify alkyl groups, followed by "amine"; di and tri prefixes where necessary
IUPAC: longest chain with N= main chain; number so N has lowest carbon, substituents named as usual; main chain name: drop e from alkane name and add "amine"; position of nitrogen number prior to alka…
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Identify Alkanes
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C&H
single bonds
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Identify Alkyl Halides
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have a halogen
F, Cl, Br, I
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Identify Alcohols
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OH
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Identify Ethers
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Oxygen
ROR
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Identify Amines
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N
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Rules for resonance
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1. Only move electrons (NOT ATOMS)
2. Must have same number of sigma bonds
3. Must have same number of unpaired electrons
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Structural Isomers
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bonding is different but have same molecular formula (n-propane and isopropane)
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Stereoisomers
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same bonding, different orientation in space
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Meso Compounds
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has two or more asymmetric centers and a plane of symmetry; have chirality centers but are achiral bc of plane of symmetry
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Substituents prefer ___. Why?
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Equatorial
1,3 diaxial interactions make bigger atoms bump into each other
Gauche interactions with ring carbons
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Axial ____ Equatorial ____ (Gauche/Anti)
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Axial- Gauche
Equatorial- Anti
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Torsional Strain
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repulsion of electrons in bonds
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Steric Repulsion
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Large atoms are better across from each other to keep them from bumping into each other
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Ring Strain
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bonds in a molecule form angles that are abnormal
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Racemic Mixture
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mixture of equal amounts of two enantiomers; optically inactive
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Absolute Configuration
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nomenclature designation used to distinguish enantiomers from each other by identifying them as "R" or "S"
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Relative Configuration
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When transforming one compound into another, none of the bonds to the chirality center were broken
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Determining The Max Number of Stereoisomers
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2^n
n= # of stereogenic centers
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Enantiomeric Excess (Optical Purity)
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Observed specific rotation/specific rotation of the pure enantiomer * 100%
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Biological Significance of Chirality
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Enzymes and Receptors are chiral making them able to distinguish between enantiomers. Enzymes and receptors will only bind to the stereoisomer whose substituents are in the correct positions to interact with their chiral binding sites.
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Which directions are R and S?
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R- clockwise
S- counterclockwise
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How can enantiomers be distinguished?
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they way they interact with plane-polarized light;
one enantiomer rotates light clockwise, its mirror image will rotate it the exact same amount counterclockwise
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Dextrorotatory
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rotates plane of polarization clockwise
+ or d
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Levorotatory
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rotates plane of polarization counterclockwise
- or l
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