Separation of Hexane and Toluene [3B]
 Mayo, pp. 115 – 117 (Please note the prior reading assignments given on p. 115!)
 In class, we will discuss a modification to the lab presented in the textbook.
 Your write-up should include the following:
1. Data from experiment
a. refractive index and % hexane (calculated) for fractions 1, 2 and 3 of the
simple distillation
b. refractive index and % hexane (calculated) for the distillate of the
fractional distillation (using the steel sponge)
2. Answer the following questions: 5-8, 5-9, 5-11, 6-17
3. Estimate how many theoretical plates your fractional distillation achieved using
Table 5.6 on p. 51.
Separation of a Three Component Mixture
Experiment [4C]
 Mayo, pp. 129 – 132 (Please note the prior reading assignments given on p. 129!)
 Your write-up should include the following:
1.
Data from experiment including masses recovered, melting points and percent
recovery calculations for each component. Comment on the purity of each
component based on the melting point data.
2. Separation scheme
3. Questions 6-21, 6-23, 6-24, 6-25
Isolation of a Natural Product: Caffeine [11B]
 Mayo, pp. 204 – 209 (Please note the prior reading assignments given on p. 206!)
 Your write-up should include the following:
1. Data from experiment including mass of recovered caffeine and percent recovery.
2. Answer the following questions:
Draw the structure of the “thermally labile, partially ionic complex” that is present in the
tea leaves.
Extraction of tea leaves with methylene chloride to remove the caffeine gives very poor
results, while extraction with a basic aqueous solution gives very good results. Explain.
Draw the structure of theobromine. From what source do we commonly ingest it?
Isolation of an Optically Active Natural Product [11A]
 Mayo, pp. 199 – 203. Please note the prior reading assignments given on p. 201.
 Your write-up should include the following:
1. Data from the experiment including final mass of usnic acid and percent extracted
from the dry lichen.
2. Answer the following questions – 6.66, 6.67, 6.68 (Ignore the information given
on the distilled water reading), 6.69, 6.70
E1 Elimination Reaction: Dehydration of 2-Butanol
Exp. [9]
 Mayo, pp. 184 – 191. Please note the prior reading assignments given on p. 186.
 Your write-up should include the following:
1. Data from the GC trace and an interpretation of results.
2. Mechanism of the reaction, showing each product formed.
3. Problems 6-56, 5-2
IR: Isolation of Cinnamon Oil from Cinnamon
Exp. [11C]
 Mayo, pp. 213 – 218. Please note the prior reading assignments given on p. 213.
 Your write-up should include the following:
1. Data from the experiment including mass of oil, percent recovery from cinnamon,
IR spectrum.
2. Structure of cinnamon oil, with an analysis of the IR spectrum.
3. Problems 6-77, 6-78, 6-79, 6-80
Halogenation: Electrophilic Aromatic Substitution
Exp. [28]
 Mayo, pp. 330 – 335.
 Your write-up should include the following:
1. Data from the experiment including mass of 4-bromoacetanilide produced,
percent yield, melting point range (comment on purity), IR data (indicate
diagnostic peaks).
2. Mechanism of the reaction.
3. A chart like the ones we have done in class for the 1H NMR spectrum on p. 333.
4. How does the 1H NMR spectrum provide evidence of the para substitution
pattern?