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# Crystallization Questions

2. The mixture will cool down as it hits the funnel and from vacuum filtration, the
mixture will turn to and produce crystals of the mixture.
7. The sulfanilamide will probably come out as a liquid or oil out rather than a crystalline
because the boiling point of the ethyl alcohol is much higher than the melting point of the
sulfanilamide during that experiment. The sulfanilamide will not crystallize and may come out
as a supercooled liquid rather than a crystal.

Distillation Questions

## 1. A. Mole fraction of Benzene: .5 or 5x 101 atm

Mole fraction of Toluene: .5 or 5x 101 atm.
b. Partial pressure of Benzene in 50 degrees Celsius mixture: 1.77x10-1 atm.
c. 1340-1010=330/10=33 mmHg per degree of Celsius for Benzene.
560-405=155/10= 15.5 mmHg per degree of Celsius for Toluene.
At 92 degrees Celsius: (1010+ (33x2)) x (0.5) + (405+ (15.5x2)) x (0.5) = 756mmHg.
At around 92 degrees Celsius, the atmospheric pressure will be 1 atm.
d. 1076/2=538 torr
436/2= 218 torr
538/756 = 71.1%
218/756 = 28.8%
e. 0.711(0.05) = 0.0355 mol in gas .288(0.05) = 0.0143
0.0355(78g/mol) = 2.77g
0.0143(92g/mol) = 1.31g
71% by mass
28% by mass
2. Looking at the phase diagram at page 732, it seems like it will take 3 theoretical plates
to get at least 70% of B.
6. If a mixture of 98% ethanol was distilled, you wont get lower than 95.6% because that is
the azeotropic condition for ethanol in water. The ethanol would boil off faster since it has a
lower boiling point until an azeotrope was created and the mixture will then release steam
at a ratio of 95.6% ethanol and 4.4 water until it boils off.

## 1. 760mmHg-227.7mmHg x 78.11g/(227.7mmHg x18.016g) = 10.144g benzene/1g H2O.

Percent composition of vapor: 532.3 mmHg/227.7mmHg = 532.3 mol/227.7 mol = 2.34
mol benzene/ 1 mol water
2.34 mol benzene x 78.11g/1 mol H2O x 18.016 = 182.78/18.016 g H2O.
182.78 Benzene/182.78+18.016 x 100% = 91%
2. At 95 degrees Celsius, the pressure is 634+118 = 752. At 96 degrees Celsius, the pressure
is 779. So the boiling point of the mixture is a little more than 95.
For every .1 C , pressure of water increases 2.3mmHg and .4 Bromobenzene.
At 95.3 C, (634mmHg + 2.3(3)) + (118mmHg + .4(3)) = 760.1 mmHg. So the boiling point is
somewhere around 95.3 C.
3. (760-733) x (123.09)/(733x18) = .251g nitrobenzene/1g H2O.
4.P-Nitrophenol does not show any intramolecular hydrogen bonding and also has
intermolecular hydrogen bonding, increasing molar mass and boiling point and thus, nonvolatile. O-nitrophenol does not have any intermolecular hydrogen bonding but has
intramolecular hydrogen bonding because of how close the substituents are, which results
in O-nitrophenol being more nonpolar and lower BP and MP.

## Resolution of Racemic alpha- PHENYLETHYLAMINE Qs

1. Resolution of Acids 2-hydroxylpropionic acid would require pure (R) 2-phenylethylamine as a resolving agents to separate the diastereomers.
Resolution of Bases An amino acid could use a basic resolving agent or an acidic chiral
active resolving agent such as the tartaric acid we used.

2. A. 2-Bromopropionic acid could be resolved using pure basic substances, which would
create diastereomer salts.
b. C11H15N is pretty neutral and amphoteric as an amine and could use either a basic or
acidic resolving agent.
c. C8H9OH would act basic with the OH group attached which would mean that we
could use acids like the tartaric acid we used in our experiment to protonate the impure
enantiomer. This creates diasteromer salts, which means it is easier to separate.