Stereochemical

absolute R / S stereochemistry:

Nomenclature

denotes absolute stereochemistry for stereogenic atoms

H Cl OH H (1S,2R)-2-chloro-1-cyclohexanol Cl OH

+ / -

refers to optical rotation. Does not correlate to absolute configuration. (+) refers to those molecules that rotate plane polarized light in a clockwise direction refers to those molecules that rotate plane polarized light in a counterclockwise direction
H N H CH 3 HO 2 C CO 2 H CH 3 N H H (R)-(-)-2-methylpiperidine

( - )

(R)-(+)-methylsuccinic acid

relative R* / S*

stereochemistry: denotes relative stereochemistry for stereogenic atoms in racemic systems with more than one stereocenter (less frequently used)
Cl OH or Cl OH

(1S*,2R*)-2-chloro-1-cyclohexanol

cis / trans

describes relationship between two substituents in cyclic systems and in simple alkenes

OH CH 3

OH CH 3

CH 3 H

CH 3 H cis

H CH 3

CH 3 H trans

cis

trans

 E / Z
CH 3 H

describes stereochemistry of alkenes (simple and more complex)

CH 3 H Z H CH 3 E CH 3 H Cl CH 3 Z CH 3 H Cl H E CH 3 OCH 3

syn / anti

describes relationship between two substituents in an acyclic system (longest chain on zig zag)
CH 3 OH OH syn OH anti CH 3 OH OH 2,3-anti; 3,4-syn; 2,4-anti CH 3 CH 3 CO 2 M e

erythro/ threo

traditional terminology used to describe relationship between two substituents on an acyclic molecule. Originally designed for glycols. With other systems gets confusing (= do not use except for glycols).
HO H R R OH H erythro HO H R H threo OH R