Organic Chemistry Flashcards
Blueprint MCAT Prep (51 cards)
IUPAC Nomenclature for Alkanes
(1) Identify and name longest carbon chain (1C = Methane, 2C = ethane, 3C = propane, 4C = butane, 5C = pentane, etc.)
(2) Label carbons such that substituents have lowest possible #’s
(3) Identify all substituents (methyl, ethyl, etc.)
(4) Place substituents in alphabetical order
Priority of Substituents in IUPAC Nomenclature of Alkanes
Other functional groups have a suffix (when they are the highest-priority group): -COOH (-oic acid) is highest priority, followed by carboxylic acid derivatives, aldehydes/ketones (suffix: -al/-one, prefix: oxo-), alcohols (suffix: -ol, prefix: hydroxy), amines (suffix: -amine, prefix: amino-), thiols (suffix: thiol, prefix: mercapto-), and hydrocarbons
Resonance
When more than one equivalent Lewis structure can be drawn for a compound. Multiple structures indicate electron delocalization.
Aromatic Compounds
Conjugated cyclic molecules with planar structure + satisfy Huckle’s rule: having 4n + 2 pi electrons, where n is 0 or an integer
Cahn-Ingold-Prelog Rules for assigning priority to substituents
(1) Look at atoms directly connected to the stereocenter; heavier atoms have higher priority
(2) If two atoms are the same, move one atom further down the substituents and re-rank by substituents.
(3) Continue until a difference is encountered; multiple bonds are higher-priority than single bonds
E/Z System for double bonds
E if higher-priority substituents are on opposite sides of double bond, Z if higher-priority substituents are on the same side
R/S System for chiral system
Orient molecule such that lowest-priority substituent faces into the page and connect substituents from high to low priority; if doing so traces a clockwise pattern
Molecule is R; if counterclock-wise, S
Chirality
Non-superimposable mirror images (enantiomers)
C must have 4 different substituents. When there is more than one chiral center, enantiomers have opposite orientation at all chiral centers, while diasteromers only differ at some
For n chiral centers, there is a maximum of 2^n stereoisomers
Alcohol
RC - OH
-ol, hydroxy-
High melting/boiling point
Aldehyde
RC(O)H
-al, oxo-
Ketone
R(C=O)R’
-one, oxo-, keto-
Carboxylic Acids
-oic acid
R(C=O)OH
High melting/boiling point
Amide
R(C=O)NH2
-amide
Ester
R(C=O)OR’
-yl, -ate
Acid Anhydride
R(C=O)O(C=O)R’
-oic anhydride
Amine
R-NH2, R-NHR
-amine, amino-
Imine
R=NH, R=NR’
Enamine
RC=CNH, C=CNHR
Mild Oxidizing Agents
PCC
Strong Oxidizing Agent
NaCr2O7, K2Cr2O7, and CrO3
Mild Reducing Agent
NaBH4
Strong Reducing Agent
LiAlH4
Factors Affecting Acidity
Resonance
Factors Affecting Reactivity
Electron-withdrawing groups, resonance, steric effect, strain
