Organic Chemistry Lecture Review: Reactions, Bases, and Alkane Nomenclature

Flashcards covering reactions involving alcohols and strong bases, the solvent leveling effect, types of strong bases used in organic chemistry, isotopic labeling, and the basic IUPAC nomenclature rules for alkanes, including identifying primary, secondary, and tertiary carbons/hydrogens, and alkyl groups.

Protonated Alcohol

An alcohol molecule that has gained an additional proton (H+).

Carbocation

A positively charged carbon species formed when a leaving group departs a molecule.

Substitution Reaction

A chemical reaction where one functional group in a molecule is replaced by another functional group.

Sodium Amide (NaNH2)

A salt (Na+ NH2-) that readily provides the strong base amide ion (NH2-).

pKa Value

A measure of the acidity of a compound, where a lower pKa indicates a stronger acid.

Solvent Leveling Effect

The phenomenon where the strength of a very strong acid or base is limited by the pKa of the solvent, meaning it cannot be stronger than the conjugate acid or base of the solvent itself.

Alkynide Ion

An anion formed by the deprotonation of a terminal alkyne, stabilized by the sp hybridized carbon.

Alkoxide (RO-)

A particularly strong base formed by the deprotonation of an alcohol, commonly used in organic chemistry.

Sodium Hydride (NaH)

A source of hydride ion (H-), a strong base used to deprotonate alcohols and create alkoxides.

Hydrogen Gas (H2)

A flammable gas produced as a byproduct when making alkoxides from alcohols and Sodium Hydride.

Ethyl Alcohol

An alcohol with two carbon atoms that can be deprotonated to form ethoxide.

Tert-butyl Alcohol

An alcohol with four carbons and a tertiary carbon attached to the hydroxyl group, which forms tert-butoxide upon deprotonation.

Alkyl Lithium Bases (RLi)

Compounds featuring a highly polarized, almost ionic carbon-lithium bond, acting as a strong source of R- (a strong base).

Hexanes

A common, inert alkane solvent that does not have extractable protons, making it suitable for reactions involving strong bases.

Deuterium Labeled Compounds

Molecules where hydrogen atoms have been replaced by deuterium (a hydrogen isotope with one neutron), often used for NMR spectroscopy or tracking.

Radio Labeling

The technique of incorporating isotopes like deuterium or tritium into molecules to track their pathway during a reaction or within a system.

Tritium

A radioactive isotope of hydrogen with two neutrons.

Unbranched Alkanes

Also called straight-chain alkanes, these are hydrocarbons where carbons are connected linearly and no carbon is attached to more than two other carbons (except at the ends).

Branched Alkanes

Alkanes that have at least one carbon atom attached to more than two other carbon atoms.

Constitutional Isomers

Molecules that have the same molecular formula but differ in the connectivity or order of their atoms.

Primary Carbon

A carbon atom bonded to only one other carbon atom.

Primary Hydrogen

A hydrogen atom attached to a primary carbon atom.

Secondary Carbon

A carbon atom bonded to two other carbon atoms.

Secondary Hydrogen

A hydrogen atom attached to a secondary carbon atom.

Tertiary Carbon

A carbon atom bonded to three other carbon atoms.

Tertiary Hydrogen

A hydrogen atom attached to a tertiary carbon atom.

Alkyl Group

A substituent derived from an alkane by removing one hydrogen atom (e.g., methyl, ethyl, propyl).

Substituents

Atomic or molecular groups that are attached to a parent or main chain of a molecule.

Longest Continuous Carbon Chain

The primary chain of carbon atoms used as the parent name in IUPAC nomenclature for alkanes.

Numbering Rule for Alkanes

Assigning numbers to the carbons of the longest chain starting from the end closest to the first substituent to give the substituent the lowest possible number.

Methyl Group

A one-carbon alkyl substituent derived from methane (-CH3).

Locant

A number used in chemical nomenclature to indicate the position of a substituent or a functional group on a parent chain.

Alkane Naming Protocol

The standard convention for naming alkanes: [Locant]-[Substituent Name][Parent Chain Name].