ACS Organic Chemistry Flashcards

Functional Groups and Basic Terminology

• Aldehyde: Compound with the -al suffix.
• Alcohol: Compound with the -ol or hydroxy- prefix.
• Ketone: Compound with the -one suffix.
• Carboxylic acid: Compound ending in -oic acid.
• Ester: Compound with the -oate suffix.
• Ether: Compound with the ether or alkoxy- prefix.
• Alkyl halides: Compounds including halogen atoms (i.e., Iodo-, Bromo-).
• Amide: Compounds ending in -amide.
• Amine: Compounds with amino- or -amine groups.

Isomerism

• Constitutional isomer: Compounds with the same atoms but different bonding arrangements.
• Stereoisomers: Molecules differing only in three-dimensional arrangement of atoms.
• Enantiomers: Stereoisomers that are non-superimposable mirror images at all stereogenic centers.
• Diastereomers: Stereoisomers with changes in configuration at some, but not all, stereogenic carbons.

Stereochemical Notation

• R: Clockwise configuration at a stereogenic center.
• S: Counterclockwise configuration at a stereogenic center.
• cis: Refers to groups on the same side in a double bond or ring.
• trans: Refers to groups on opposite sides in a double bond or ring.
• E: Trans configuration in alkenes.
• Z: Cis configuration in alkenes.
• Ortho: 1,2 substitution pattern on a benzene ring.
• Meta: 1,3 substitution pattern on a benzene ring.
• Para: 1,4 substitution pattern on a benzene ring.

Naming Protocols

• Esters: Named using the alkyl from the alcohol first, followed by the alkyl from the carbonyl ending in "-oate."
• Substituted amides: Begin with the name of the nitrogen-substituted group followed by the carbonyl group ending in "-amide."

Huckel's Rule

• Equation: Huckel's numbers = 4n + 2.
• Significance: Determines the number of pi electrons in aromatic systems.

Lewis Structures

• Draw by calculating total valence electrons and arranging to complete octets around each atom.

Acidity Concepts

• Relationship between free energy and acidity: Lower free energy in proton loss indicates higher acidity.
• Gibbs free energy equation for acids: ΔG = -RTln([A-][H3O+]/[HA][H2O]).
• Acidity factors: Analyzed using MARIO minus M (Atom, Resonance, Induction, Orbitals).

Nucleophilicity and Mechanisms

• Strong bases prefer SN2 or E2 reactions.
• Nucleophilicity improves with molecule size in polar protic solvents; larger nucleophiles are favored.
• Non-polar solvents enhance bimolecular mechanisms by preventing charged leaving groups from departing.

Reaction Dynamics

• Heat favors elimination reactions over substitution.
• Protonation of epoxides allows for nucleophile attack at more substituted carbons.
• Racemic mixtures have different boiling points compared to pure enantiomers.

Specialized Compounds

• Imine: Formed from carbonyl carbon and ammonia, results in C=N bond.
• Enamine: Alkene connected to a substituted amine through carbonyl attack.

Oxidation Agents Usage

• Chromium agents are effective in acidic conditions; manganese agents are used in basic conditions.
• Anhydrous chromium agents like PCC provide partial oxidation compared to complete oxidation from others.

Reactions and Cleavage

• Haloform reaction converts methyl ketones into carboxylic acids via halogenation and neutralization.
• Ozone cleavage of alkenes produces ketones and aldehydes.
• Periodic acid cleaves cis-1,2-diols.

Miscellaneous

• The first step in acetal formation involves protonation of oxygen.
• Stability potential of lone pairs follows sp > sp2 > sp3 in hybridization, influencing acidity trends.