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Organic Chemistry on the MCAT

June 25th, 2011  |  Published in MCAT Prep

Carbon Atomic Mass

Fortunately, all of the information you learned in Organic Chemistry lecture will not be on the MCAT. However, a majority of this material will be. Here is a list of the topics potentially covered in the Organic Chemistry portions of the biological sciences section of the MCAT. If you click the link, you will connect to a list of resources to study that topic.

THE COVALENT BOND
A. Sigma and Pi Bonds
1. Hybrid orbitals (sp3, sp2, sp, and their respective geometries)
2. Valence shell electron-pair repulsion (VSEPR) theory, predictions of shapes of molecules (e.g., NH3, H2O, CO2)
3. Structural formulas
4. Delocalized electrons and resonance in ions and molecules

B. Multiple Bonding
1. Its effect on bond length and bond energies
2. Rigidity in molecular structure

C. Stereochemistry of Covalently Bonded Molecules
1. Isomers
a. constitutional isomers
b. stereoisomers (e.g., diastereomers, enantiomers, cis and trans isomers)
c. conformational isomers
2. Polarization of light, specific rotation
3. Absolute and relative configuration
a. conventions for writing R and S forms
b. conventions for writing E and Z forms
4. Racemic mixtures, separation of enantiomers

MOLECULAR STRUCTURE AND SPECTRA
A. Absorption Spectroscopy
1. Infrared region
a. intramolecular vibrations and rotations
b. recognizing common characteristic group absorptions, fingerprint region
2. Visible region
a. absorption in visible region yielding complementary color
b. effect of structural changes on absorption
3. Ultraviolet region
a. electron and nonbonding electron transitions
b. conjugated systems
B. Mass Spectrometry
1. Mass-to-charge ratio (m/z)
2. Molecular ion peak
C. 1H NMR Spectroscopy
1. Protons in a magnetic field, equivalent protons

SEPARATIONS AND PURIFICATIONS
A. Extraction (Distribution of Solute Between Two Immiscible Solvents)
B. Distillation
C. Chromatography (Basic Principles Involved in Separation Process)
1. Gas–liquid chromatography
2. Paper chromatography
3. Thin-layer chromatography
D. Recrystallization (Solvent Choice from Solubility Data)

HYDROCARBONS
A. Alkanes
1. Description
a. nomenclature
b. physical properties
2. Important reactions
a. combustion
b. substitution reactions with halogens, etc.
3. General principles
a. stability of free radicals, chain reaction mechanism, inhibition
b. ring strain in cyclic compounds
c. bicyclic molecules

OXYGEN-CONTAINING COMPOUNDS
A. Alcohols
1. Description
a. nomenclature
b. physical properties
2. Important reactions
a. substitution reactions (SN1 or SN2, depending on alcohol and derived alkyl halide)
b. oxidation
c. pinacol rearrangement in polyhydroxyalcohols, synthetic uses
d. protection of alcohols
e. reactions with SOCl2 and PBr3
f. preparation of mesylates and tosylates
g. esterification
h. inorganic esters
3. General principles
a. hydrogen bonding
b. acidity of alcohols compared to other classes of oxygen-containing compounds
c. effect of chain branching on physical properties

B. Aldehydes and Ketones
1. Description
a. nomenclature
b. physical properties
2. Important reactions
a. nucleophilic addition reactions at C=O bond
i. acetal, hemiacetal
ii. imine, enamine
b. reactions at adjacent positions
i. haloform reactions
ii. aldol condensation
iii. oxidation
c. 1,3-dicarbonyl compounds, internal hydrogen bonding
d. keto–enol tautomerism
e. organometallic reagents
f. Wolff–Kishner reaction
g. Grignard reagents
3. General principles
a. effect of substituents on reactivity of C=O; steric hindrance
b. acidity of α hydrogens; carbanions
c. α, −unsaturated carbonyl compounds, their resonance structures

C. Carboxylic Acids
1. Description
a. nomenclature
b. physical properties and solubility
2. Important reactions
a. carboxyl group reactions
i. nucleophilic attack
ii. reduction
iii. decarboxylation
iv. esterification
b. reactions at α position
i. halogenation
ii. substitution reactions
3. General principles
a. hydrogen bonding
b. dimerization
c. acidity of the carboxyl group
d. inductive effect of substituents
e. resonance stability of carboxylate anion

OXYGEN-CONTAINING COMPOUNDS
A. Alcohols
1. Description
a. nomenclature
b. physical properties
2. Important reactions
a. substitution reactions (SN1 or SN2, depending on alcohol and derived alkyl halide)
b. oxidation
c. pinacol rearrangement in polyhydroxyalcohols, synthetic uses
d. protection of alcohols
e. reactions with SOCl2 and PBr3
f. preparation of mesylates and tosylates
g. esterification
h. inorganic esters

D. Acid Derivatives (Acid Chlorides, Anhydrides, Amides, Esters)
1. Description
a. nomenclature
b. physical properties
2. Important reactions
a. preparation of acid derivatives
b. nucleophilic substitution
c. Hofmann rearrangement
d. transesterification
e. hydrolysis of fats and glycerides (saponification)
f. hydrolysis of amides
3. General principles
a. relative reactivity of acid derivatives
b. steric effects
c. electronic effects
d. Strain (e.g., -lactams)

E. Keto Acids and Esters
1. Description
a. nomenclature
2. Important reactions
a. decarboxylation
b. acetoacetic ester synthesis
3. General principles
a. acidity of α hydrogens in -keto esters
b. keto-enol tautomerism

AMINES
1. Description
a. nomenclature
b. stereochemistry, physical properties
2. Important reactions
a. amide formation
b. reaction with nitrous acid
c. alkylation
d. Hofmann elimination
3. General principles
a. basicity
b. stabilization of adjacent carbocations
c. effect of substituents on basicity of aromatic amines