13 Foundations of Organic Chemistry (Video Notes)

Vocabulary flashcards covering key terms and concepts from the Foundations of Organic Chemistry lecture notes.

Carbon bonding

Carbon forms covalent bonds with H, O, N, S, and halogens, enabling a vast array of organic structures.

Functional group

Specific atoms or groups in a molecule that determine its chemical behavior (e.g., -OH, >C=O, -COOH, -NH2, -X).

Isomerism

Compounds with the same molecular formula but different atom arrangements or connectivity.

Structural (constitutional) isomerism

Isomers with identical formulas but different connectivity of atoms.

Chain (skeletal) isomerism

Structural isomerism arising from different carbon chain arrangements (straight vs branched).

Butane isomers

n-Butane (straight chain) vs. isobutane (branched chain).

Position isomerism

Different position of a functional group, double bond, or substituent along the carbon chain.

Functional group isomerism

Same formula but different functional groups (e.g., propanal vs acetone).

Metamerism

Same functional group but different alkyl groups attached to it (common in ethers, esters, amines).

Tautomerism

Dynamic equilibrium between tautomers differing mainly by hydrogen position and a double bond (e.g., keto–enol).

Stereoisomerism

Isomers with the same connectivity but different 3D arrangement.

Geometrical isomerism

Cis/trans or E/Z isomerism due to restricted rotation around double bonds or rings.

Enantiomer

Non-superimposable mirror images; a pair of optical isomers.

Chirality

A property of molecules that have a chiral center—usually a carbon with four different groups.

R/S configuration

Absolute configuration using CIP rules; R = clockwise, S = counterclockwise.

Dextrorotatory and levorotatory

Enantiomers that rotate plane-polarized light; dextrorotatory (+) rotates clockwise, levorotatory (−) counterclockwise.

Diastereomerism

Stereoisomers that are not mirror images (e.g., D-, L-, and meso-tartaric acid).

Conformational isomerism

Rotation around single bonds leading to different conformers; may be in dynamic equilibrium.

Conformers in acyclic molecules

Ethane: staggered (most stable) vs eclipsed (least stable); ~12 kJ/mol barrier.

Butane conformers

Anti (most stable) with CH3 groups 180° apart; gauche (less stable) at 60°; eclipsed forms are least stable.

Cyclohexane conformations

Chair (most stable) vs boat (less stable); axial vs equatorial; bulky groups prefer equatorial.

Equatorial vs. axial

Positions on cyclohexane; equatorial minimizes 1,3-diaxial interactions.

Newman projection

A view along a C–C bond to compare rotation and conformations (front/back carbons).

IUPAC nomenclature

Systematic naming using Prefix + Root + Suffix; prefix = substituents, root = longest chain, suffix = main group.

Longest carbon chain

Identify the longest continuous chain as the root of the name.

Numbering for functional groups

Number the chain to give the lowest locant to the principal functional group (e.g., OH).

Substituents naming

Name substituents and their positions (e.g., 2-methyl).

Suffix selection

Choose the suffix that reflects the main functional group (e.g., -ol for alcohol).

IUPAC naming steps (example)

Long chain, number to place OH at C1, identify substituents, apply -ol suffix, assemble name.

Example IUPAC name

2-methylbutan-1-ol from CH3-CH(CH3)-CH2-CH2-OH.

Propane, Prop-1-ene, Ethanol, Propanoic acid, 2-Methylpropane

Examples of common IUPAC names: propane, prop-1-ene, ethanol, propanoic acid, 2-methylpropane.

Empirical formula

The simplest whole-number ratio of atoms in a compound; does not show actual bonding or arrangement.

Structural formula

A detailed depiction of how atoms are connected and bonded in a molecule; includes full, condensed, and skeletal forms.

Empirical formula examples

Glucose = CH2O; Hydrogen peroxide = HO; Benzene = CH (empirical ratio 1:1).

3D carbon tetrahedral angle

Around a carbon in sp3 hybridization, the H–C–H angle is ~109.5°.

Hydrocarbons

Compounds composed of carbon and hydrogen; include alkanes, alkenes, alkynes, and aromatics.

Alkanes, Alkenes, Alkynes

Alkanes: single bonds (saturated); Alkenes: one or more C=C; Alkynes: one or more C≡C.

Aromatic hydrocarbons

Contain benzene rings and exhibit special stability due to delocalized electrons.

Reaction mechanisms

Common organic reaction patterns: addition, substitution, elimination, and redox.