MCAT organic chemistry mnemonics
Addition of Amine to Carbonyl Group
“SE PI” (or “SEe PIe”)
Secondary amine ? Enamine
Primary amine ? Imine
(Note: tertiary and quaternary amines do not react with the C=0 group.)
Cis/trans (Geometric) Isomers
“Z: Zame Zide
E: Epposite”
Z for same side and E for opposite sides
Conformations
Gauche conformation: It’s “gauche” (inappropriate) for one methyl group to stand too
close to another group.
Cyclohexane ring: When you have low energy, you sit down in a “CHAIR” to rest. “BOATS”
can be tippy, so they are less stable.
Isomers
“SS - ED - CC”
Isomers of a sugar: If the second lowest -OH is on the Left, the molecule is L.
If the -OH is on the Right, it’s D.
Meso Compounds
“MeSo compounds have a Mirror of Symmetry”
Thus, even though they may have stereogenic centers, they are achiral and so do not have
enantiomers.
NMR
Downfield is Deshielded.
Meta-Directing Groups on a Benezene Ring
“Queen Elizabeth Second’s Navy Commands, Controls, Communicates”
Q Quaternary amino -NR3+
E Ester -COOR
S Sulfonic acid -SO3H
N Nitro -NO2
C Carbonyl -CHO
C Carboxyl -COOH
C Cyano -CN
Ortho- and Para- Directing Groups on a Benezene Ring
“AHA AHA P”
A Alkyl -R
H Halogen -X
A Alkoxyl -OR
A Amino -NH2, -NHR, -NR2 (not -NR3+)
H Hydroxyl -OH
A Amide -NHCOR
P Phenyl -C6H5
Types of Reactions
“SEA MOuRNS CANned PEAs”
Substitution Electrophilic - Aromatic
Most Other Reactions - Nucleophilic Substitution
Carbonyl - Addition Nucleophilic
Pi bonds - Electrophilic Addition
HAL = basic amino acids (Histidine, Arginine, Lysine); courtesy of examkrackers…
Nonpolar (hydrophobic) amino acids:
I saw (ISO) LEUcy METHodically PRObe and PHEel ALAN and then VAL TRYPped on the GLYCINE
(This would be Isoleucine, Leucine, Methionine, Proline, Phenylalanine, Alanine, Valine,
Tryptophan, Glycine)
Actions of some hormones:
INsuline makes glucose go INto the cell.
GlucaGON makes glucose GONE from the cell.
CalciTONin TONES down calcium concentrations in the blood.
STRONG ACIDS (in order of decreasing acidity)::
HI - I
HBr - Bring
HCl - Cans of
HClO4 - Coca
HClO3 - Cola
H2SO4 - So
HNO3 - No
