Name: CHEM 245- Midterm-like questions NO CALCULATORS ALLOWED IN THE EXAM 1. A compound boils at 400 F at atmospheric pressure.

Since it decomposes easily at elevated temperatures, you need to bring the bp down to 60 C. In the lab, you have a vacuum pump that allows you to drop the pressure to 200 mm Hg. (a) What is the bp now? (5p) (b) At what pressure is the bp 60 C? (5p) (b) How much water per gram of compound do you need to add (under the conditions of point a) to make it boil at 60 C? Pwater @60C = 150 mm Hg and molecular wt of compound = 100 and it is immiscible with water. 7.5p (c) How much water do you need if the pump is not available? 7.5p.

3-8 mm Hg

150 C or 300 F

2. Why is water not used to put out most fires in organic laboratories? (5 pts)

3. (a)What separation technique would you use to separate a mixture of A, B, C, and D? Describe (diagram) the sequence of chemical transformations. (20p) (b)Arrange them in the order of their Rfs. (5p) (use back of page)

CH3 NO2

OH

COOH NH2

CH3

CN CH3 OH OCH3

COOH OCH 3

NH 2

4. If you accidentally spill strong base on your skin, which of the following should you do first? (5 Pts) (a) wash with a weaker base (b) wash with plenty of hot water (c) wash with HCL (d) stop crying and pour more of the strong base (e) call 1-800-IAM-BASE and follow the instructions (f) wash with tap water 5. Why is a fluted (vs. an unfluted) paper used in gravity filtration? (5p) 6. Why must the spot be applied above the level of the developing solvent in TLC? (5p). 7. Why is it necessary to remove the stopper from a separatory funnel when the liquid is being drained from it through the stopcock? (5p).

8. The solubilities of compound A in chloroform and water are 10g/100mL and 2.5 g/100mL. (a) What is the distribution coefficient? 4p (b) How much (mole fraction) compound can be extracted from 1L of saturated water solution of A with 100 mL chloroform? 7p 2

(c) How much will you obtain by a subsequent extraction with 200 mL chloroform? 7p (d) How much could you extract with 3 - 100 mL portion of solvent? (e) How much chloroform (V2) is necessary to remove 90% of the initial A from the water phase in a single extraction? 7p. 9. You prepared aspirin and were concerned that it was impure with excess salicylic acid. Which of the following would NOT give any information about this? 5 Pts A) Infrared spectrum of the aspirin B) Melting point of the aspirin C) Smell of the aspirin D) The weight of the product E) Both C and D 10. What is good circumstantial evidence that a compound is pure? 5 Pts (a) Good solubility in methylene chloride (b) Narrow boiling range (c) Sharp melting point (d) Nice color (e) Pleasant smell 11. Vigorous mixing of a water/benzene frequently leads to the formation of an emulsion. Which of the following may help in the break-up of the emulsion? 5 Pts (a) add some coca-cola (b) add sprite (c) add NaCl (d) add charcoal (e) add Na 12. If you accidentally spill strong acid on your skin, which of the following should you do first? 5 Pts (g) wash with a weaker acid (h) wash with NaCl (i) wash with plenty of water (j) wash with NaOH (k) have your dog lick the wound (l) call 1-800-IAM-ACID and follow the instructions 13. What is the Kugelrohr and what is it used for? 10 Pts

14. Draw qualitatively (show integrals, # of Hs, chemical shifts) the 1H-NMR spectra of the compounds below: (use back of the page). 25p. (a)
OCH3 NaO Br H3C ONa ONa

(b)

(c)

CH3

(d)

H3C

O H3C OCH3

15. Similarities and differences in the solvent selection criteria for recrystallization, TLC, extraction and NMR.