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Organic Chemistry: Structure & Stereochemistry

Free MCAT study guide — Chemical and Physical Foundations of Biological Systems

Hybridization & Bonding

HybridizationGeometryBond AngleExample
sp³Tetrahedral109.5°CH₄, sp³ N in amines
sp²Trigonal planar120°C=C (alkenes), C=O (carbonyls)
spLinear180°C≡C (alkynes), C≡N (nitriles)

Stereochemistry

R/S configuration assignment
R/S configuration assignment

Types of Isomers

  • Constitutional (structural): Same formula, different connectivity
  • Enantiomers: Non-superimposable mirror images (opposite at ALL stereocenters)
  • Diastereomers: Stereoisomers that are NOT mirror images (differ at SOME stereocenters)
  • Meso compounds: Have stereocenters but optically inactive (internal mirror plane)
Key Point: Enantiomers have identical physical properties EXCEPT optical rotation. Diastereomers have DIFFERENT physical properties.
ee = |observed [α]| / |pure [α]| × 100%

Functional Groups

Major organic functional groups
Major organic functional groups

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