2. (12 pts) The compounds in each box below are placed in a separatory funnel containing hexane and water. The mixture is then shaken with the reagent over the arrow. Circle the compound that will be most soluble in the indicated layer.

O

CH3

NO2O2N

N

NH

NaOH

HCl

NH2

O

OH

CH3

O

HO OH

Compound in the aqueous layer

Compound in the aqueous layer

Compound in the aqueous layerCH3

3. (15 points) Match the pKa values to the structures (put the number below the structure in the box). Note you will only use each value once and there are more values than what you need.

HO

O

HO F

OH

F

ClHO

O

ClCl

–5 1 4.5 8.5 12 17 20 22 25 36 43 50–7 103 15

F F

O

O

HO OH

Shake/mix Compound in the organic layerCH3

Shake/mix

O

50 4.5 –7 12 1

2