ch3

Heterolysis

Homolysis

Bronsted Lowry definition

Lewis definition for acids and bases

Nucleophile

electron rich

gives electron pair to another thing (losses electrons)

(negative charge, lone pairs, pi bonds)

lewis bases

carbanion

electrophile

positive charge, incomplete octet

carbocation

Basically, look at conjugative bases. If structure gained a proton = base = electrophile

If structure lost a proton = acid = nucleophile

Describe arrow pushing

Go from lone pairs/negative charge/pi bond → another atoms

from nucleophile to electrophile

Ka and pKa relativity to acid strength

pKa UP → acid strength DOWN

Ka UP → acid strength UP

Strong acid → weak conjugate base

Weak acid → strong base

Be able to predict the outcome of acid/base reactions and the direction of the

equilibrium.

1. Identify Acid on each side

2. compare pka value for the acids

EQUILIBRIUM FAVORS THE SIDE WITH THE HIGHER pKA

Understand why many organic acid/base reactions are carried out in nonaqueous solutions due to the leveling effect of water.

Some acid/base reactions are not carrier out in aqueous solution because aqueous solutions cause acids stronger than hydronium to completely convert into hydronium when they dissolve in water.

For bases, they transform into OH

The point of doing these reaction in nonaqueous solutions is so reactions are actually carried out rather than being prevented by water, and so that the true acid strengths and bases strength of the compound being used can actually be observed rather than being limited by water

Strongest acid in water - hydronium H3O+

Strongest base in water = hydroxide OH-

Recognize organolithium reagents and their role as very strong bases.

Organolithium reagents are those that are [carbon—metal] bonds

Like C—-Li

These are super strong bases because the C-Li is highly polarized as the carbon cleaves like a carbanion.

These are also super strong bases because the C-Li bonds the associated carbanions happen to be the conjugate bases of alkanes which have a high pKa (high pKa → strong base & weak acid)

Super strong bronsted bases

Strong nucleophiles

these cannot be used in water because the reagent would only survive in very low acidity solvents like hydrocarbons

Carboxylic acid pKa

2-5

alcohols pKa

16-18

phenols pKa

10

terminal alkynes pKa

25