• periodic trends
• element effect
• resonance
• polar effect
• solvation

• salvation stabilizes A^- and increases acidity

A-H ---> A^- + H⁺

• the higher the pKa value the weaker the acidity

as methyl, secondary, or tertiary, depending on the number of alkyl groups attached to the carbon bearing the halogen

methyl-no alkyl groups

primary-one

secondary-two

tertiary-three

has a permanent dipole moment

ex: methyl chloride, methanol, diethyl ether, propane

even though two compounds may have similar molecular masses, their BPs might be different because they have different molecular shapes and sizes.

large intermolecular attractions translate into high BPs so alkanes have higher BPs than alkyl halides

a substance that can either lose or gain a proton.

ex: alcohols and thiols

the acidity of an alcohol is the loss of a proton

the basicity of an alcohol is the gain of a proton

compounds that contain carbon-metal bonds

ex: oxymercuration and organoboranes

a compound of the form R-Mg-X

X= Br, Cl, I

ex: ethylmagnesium bromide

CH₃CH₂-Mg-Br

compounds in the form R-Li

ex: butyllithium

CH₃CH₂CH₂CH₂-Li

using ether solvents to add an alkyl halide to a metal

CH₃CH₃-Br + Mg -----------> CH₃CH₂-Mg-Br

(C₂H₅)₂O

they are soluble in hydrocarbons.

Grignard and organolithium reagents react violently with oxygen and vigorously with water

Carbanions are carbons bearing three bonds, an unshared pair of electrons, and a negative formal charge.

Grignard and organolithium reagents react as if they were carbanions:

R₃-C-MgX ----> R₃C:^-     MgX⁺