Leaving groups ordered in decreasing ability to leave

R–N2+

dinitrogen

R–OR'2+

dialkyl ether

R–OSO2R

perfluoroalkylsulfonates (e.g. triflate)

R–OTs, R–OMs, etc.

tosylates, mesylates and similar sulfonates

R–I

iodide

R–Br

bromide

R–OH2+, R'–OHR+

water, alcohols

R–Cl

chloride

R–ONO2, R–OPO(OR')2

nitrate, phosphate, and other inorganic esters

R–SR'2+

thioether

R–NR'3+, R–NH3+

amines, ammonia

R–F

fluoride

R–OCOR

carboxylate

R–OAr

phenoxides

R–OH, R–OR

hydroxide

R–NR2

amides

R–H

hydride

R–R'

arenide, alkanide