From rich to poor

Section 2 of 4

Electrons carry a negative charge, so they are drawn toward positive charge. Curly arrows run from places with electrons to spare to places that are short of them.

An electron-rich place has electrons to give: a lone pair, a negative ion, or a C=C double bond. A double bond holds four electrons between two carbons. Its second pair sits above and below the line between the atoms, where other molecules can reach it.

An electron-poor place is short of electrons. An H⁺ has none at all. A δ+ atom, as in lesson 11, has had part of its share pulled away by a stronger puller next to it: the hydrogen of an O–⁠H bond, or the carbon of a C=O.

Electron-rich and electron-poor places Two columns, with an arrow from the left heading to the right heading. Left, electron-rich: ammonia, H3N, with a lone pair on its nitrogen; ethene, H2C=CH2, with one line of its double bond amber; and a hydroxide ion, H-O, with a lone pair and a minus charge. Right, electron-poor: a hydrogen ion, H plus; an O-H bond with delta minus on the oxygen and delta plus on the hydrogen; and a C=O bond with delta plus on the carbon and delta minus on the oxygen. H3NH2CCH2HOOHCO electron-rich electron-poor a lone pair a C=C double bond − a negative ion H + a hydrogen ion δ− δ+ a δ+ hydrogen δ+ δ− a δ+ carbon
Electron-rich places (left) have electrons to give, and electron-poor places (right) take them. Curly arrows run from rich to poor.

Givers and takers

Chemists have a name for each partner. A nucleophile gives a pair of electrons to make a new bond. The name means "nucleus-loving": it heads for positive charge, like the positive nucleus of an atom. An electrophile takes a pair of electrons, and its name means "electron-loving".

When ammonia picked up an H⁺, ammonia was the nucleophile and the H⁺ the electrophile. A curly arrow that makes a new bond starts on a nucleophile and points to an electrophile.

Nucleophiles and electrophiles
NucleophileElectrophile
electron-richelectron-poor
gives a pair of electronstakes a pair of electrons
ammonia, OH⁻, etheneH⁺, the δ+ carbon of a C=O

Quick check

Which of these is an electrophile?