Fundamental Principles of Organic Chemistry: MDCAT Notes and MCQs
Definitions
- Organic chemistry: chemistry of carbon compounds (hydrocarbons and their derivatives) — excluding CO, CO2, carbonates, cyanides, carbides.
- Vital force theory (Berzelius) was disproved by Wöhler (1828), who synthesized urea from ammonium cyanate.
- Carbon's special features: tetravalency, catenation, multiple bonds, isomerism.
Structural classification
- Open-chain (acyclic / aliphatic): straight or branched — alkanes, alkenes, alkynes.
- Closed-chain (cyclic):
- Homocyclic / carbocyclic (ring of only C): alicyclic (cyclohexane) and aromatic (benzene, naphthalene).
- Heterocyclic (ring contains N, O or S): pyridine, furan, thiophene, pyrrole.
Functional groups
An atom or group of atoms that determines the characteristic properties of a compound.
| Class | Group | Class | Group |
|---|---|---|---|
| Alcohol | –OH | Carboxylic acid | –COOH |
| Ether | R–O–R | Ester | –COOR |
| Aldehyde | –CHO | Amine | –NH2 |
| Ketone | >C=O | Amide | –CONH2 |
| Alkyl halide | –X | Nitrile | –C≡N |
Isomerism
Structural isomers differ in connectivity (chain, position, functional group, metamerism, tautomerism). Stereoisomers have the same connectivity but different spatial arrangement:
- Geometric (cis–trans) isomerism: needs restricted rotation (C=C or ring) and two different groups on each double-bonded carbon. cis-2-butene vs trans-2-butene; maleic (cis) vs fumaric (trans) acid. Cis isomers usually polar with higher b.p.; trans more stable, higher m.p. 1-butene shows no geometric isomerism.
- Optical isomerism: needs a chiral (asymmetric) carbon with four different groups. Non-superimposable mirror images = enantiomers; rotate plane-polarized light equally in opposite directions (d/+ and l/−). Equimolar mixture = racemic mixture (optically inactive). Examples: lactic acid, 2-butanol, glyceraldehyde, amino acids (except glycine).
PMDC learning outcomes for this unit
- Organic compounds: 13.1 Define organic chemistry and organic compound.
- Organic compounds: 13.2 Classify organic compounds on structural basis.
- Organic compounds: 13.3 Define functional group.
- Organic compounds: 13.4 Explain stereoisomerism and its types.