lab practical: lab 5 - separation of 3 component mixture

What type of extraction was done during this lab?

liq-liq extraction (or acid/base extraction

what is liq-liq/acid-base extraction?

it involves the exploitation of ea. compounds acid/base properties to move compounds between immiscible aqueous and organic layers during the experiment. solubility changes as the compounds become more protonated/deprotonated (aka it effect which layer they reside in)

what was the starting material of lab 5: separation of 3 component mixture?

a basic, neutral, and acidic component

what was the basic component? draw it.

benzocaine

what was the neutral component? draw it.

diphenylmethanol

what was the acidic component? draw it.

it could have been:

benzoic acid

2-methocybenzenoic acid

o-toluic acid

what was the organic layer?

ethyl acetate

what was the aqueous layer?

water

was the ethyl acetate the upper or lower? Why

ethyl acetate was the upper layer; it was upper because its density was less than water

was the water the upper or lower? Why

water was the lower layer; it was the lower because its density was greater than the ethyl acetate

How did we use IR for lab 5:

we used IR to confirm the identity of the basic and neutral component and identify the acidic component

how did we use HNMR?

we used IR to confirm the identity of the basic and neutral component and identify the acidic component

ionization effects on solubility: what happens when organic acids or bases become ionized?

neutral components are water soluble, when you give a neutral compound a charge (+/-) they go into the aqueous layer

what do acids react with to become charged? bases?

acids react with bases and bases react with acids

memorize the flow chart mechanism

...

If ethyl acetate is the organic layer, will it be the top or bottom layer? What about diethyl ether? What about DCM?

ethyl acetate: upper

diethyl ether: upper

DCM: lower

what solution was used to precipitate out your final product: basic component

6M NaOH

what solution was used to precipitate out your final product: acidic component

6M HCl

what is the ONLY solvent we would deal with more dense than water? what does this mean?

DCM is the only solvent denser; this means any other solvent the organic layer will be the upper layer (but with DCM the organic layer would be the bottom)

define: immiscible

when i mix two solvents together they separate into twp layers

T/F: most organic solvents are immiscible with water

true

what organic solvent is NOT immiscible with water?

alcohols

what would be an example of a bad solvent to use with water if you want two layers so you can extract an organic compound from water?

methanol

what functional group made the acidic component acidic?

carboxylic acid

what functional group made the basic component basic?

the amine

if you wanted to extract the basic or acidic component into the aqueous layer, i would need to ionize them. How would i do that?

Basic component: ~2M HCl

acidic component: ~1M NaOH