Alicyclic Chemistry Vocabulary

Flashcards of key vocabulary terms related to alicyclic chemistry from the lecture notes.

Alicyclic Chemistry

The chemistry of ring-shaped compounds.

Cycloalkanes (Alicyclic Compounds)

Cyclic alkanes with carbon atoms arranged in a ring.

Cyclo

Prefix added to the alkane name to name simple cycloalkanes.

Nomenclature Rule 1 for Cycloalkanes

The cyclic or acyclic portion that contains more carbons determines the base name.

Nomenclature Rule 2 for Cycloalkanes

Carbons are numbered to give the lowest numbers for substituted carbons.

Angle Strain

Expansion or compression of bond angles away from most stable angle.

Torsional/Bond Strain

Due to the eclipsing of bonds on neighboring atoms.

Steric Strain

Repulsive interactions between non-bonded atoms in close proximity.

Ring Strain

Combination of angle and torsional strains.

Cyclopropane

The most strained cycloalkane due to angle and torsional strain; enforced 60° bond angle.

Cyclobutane

Adopts a slightly puckered conformation with bond angles of 88° to reduce torsional strain.

Cyclopentane

Adopts a puckered ‘envelope’ conformation to reduce torsional strain.

Cyclohexane

The most common cycloalkane in nature and organic chemistry.

Chair Conformation

The most stable conformation for cyclohexane, with all bond angles at 109.5° and no eclipsed C-H bonds.

Boat Conformation

A cyclohexane conformation that avoids angle strain but has torsional strain due to flagpole hydrogens.

Axial Bonds

C-H bonds that point straight up and down in cyclohexane.

Equatorial Bonds

C-H bonds that point out from the ring in cyclohexane.