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Solution Manual for A Small Scale Approach to Organic Laboratory Techniques, 3rd Edition
Solution Manual for A Small Scale Approach to Organic Laboratory Techniques, 3rd Edition
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Experiment 1SOLUBILITY
TIME ESTIMATE: Parts A-D (3 hours); Part E (1 hour); Part F (1 hour)
CHEMICALS AND SUPPLIES PER 10 STUDENTS:
Part A
Benzophenone (Grind up the flakes into a powder) 0.5 g
Malonic acid 0.5 g
Biphenyl 0.5 g
Methyl alcohol 40 mL
Hexane 40 mL
Part B
Methyl alcohol 13 mL
1-Butanol 13 mL
1-Octanol 13 mL
Hexane 40 mL
Part C
Ethyl alcohol 13 mL
Diethyl ether 13 mL
Methylene chloride 25 mL
Hexane 13 mL
Part D
Benzoic acid 1.2 g
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© 2011 Brooks/Cole, Cengage Learning
, Ethyl 4-aminobenzoate 1.2 g
1M NaOH 25 mL
1M HCl 25 mL
6M NaOH 6 mL
6M HCl 6 mL
Litmus paper
Part E
1. Acetone 25 mL
Hexane 13 mL
2. We give each pair of students two mixtures. Each mixture
contains 2 mL of each liquid and about 0.1 g of the dissolved
solid. There are many possible combinations of substances to
use. The mixtures we have used contain one of the following
combinations of solid and liquids (the solid is listed first):
fluorene, methylene chloride, water; triphenylmethanol, diethyl
ether, water; salicylic acid, methylene chloride, 1M NaOH;
ethyl 4-aminobenzoate, diethyl ether, 1M HCl; naphthalene,
hexane, water; benzoic acid, diethyl ether, 1M NaOH;
p-aminoacetophenone, methylene chloride, 1M HCl. The
mixtures containing ethyl 4-aminobenzoate and
p- aminoacetophenone should be made up fresh on the same day
as the lab, otherwise the solutions become colored.
3. Tetraphenylcyclopentadienone 0.3 g
Methyl alcohol 13mL
Part F
Self-Assembled Monolayer Demonstration Kit
Available from Asemblon, Inc., 15340 N.E. 92nd St., Suite B,
Redmond, WA 98052; phone 425-558-5100; asemblon.com.
Instructions for filling the Asemblon pen with the thiol are provided
with the kit.
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© 2011 Brooks/Cole, Cengage Learning
, If done as a demonstration, one kit is sufficient. Otherwise one kit
for every 4 students works well.
Butane to fill the torch for erasing the gold slide
Methyl alcohol 10 mL
Acetone 10 mL
CAS Registry numbers:
Benzophenone 119-61-9
Malonic acid 141-82-2
Biphenyl 92-52-4
Hexanes 73513-42-5
Methyl alcohol 67-56-1
1-Butanol 71-36-3
1-Octanol 111-87-5
Ethyl alcohol (ethanol), 95% 64-17-5
Diethyl ether 60-29-7
Methylene chloride 75-09-2
Benzoic acid 65-85-0
Ethyl 4-aminobenzoate 94-09-7
Acetone 67-64-1
Fluorene 86-73-7
Triphenylmethanol 76-84-6
Salicylic acid 69-72-7
Naphthalene 91-20-3
p-Aminoacetophenone 99-92-3
Tetraphenylcyclopentadienone 479-33-4
SPECIAL NOTES
In Part A, it is very important that students follow the instructions
carefully for stirring the mixtures. The bigger spatula shown in Figure 12.10 on
page 697 of the Textbook is very effective in achieving consistent stirring from
one mixture to another.
We have found that some students have difficulty performing Critical
Thinking Application #2 (p. 9 of the Text) on the same day that they complete
the rest of this experiment. Many students need time to assimilate the material
in this experiment before they can complete this exercise successfully. One
approach is to assign Critical Thinking Applications from several technique
experiments (for example, Experiments 1 - 3) on a laboratory period following
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© 2011 Brooks/Cole, Cengage Learning
, the completion of the individual technique experiments. This provides an
effective way of reviewing some of the basic techniques.
Part A (expected results)
Compound Water Methyl alcohol Hexane
Benzophenone Insoluble Soluble in about Soluble in about
25 sec 60 sec
Malonic acid Soluble in about Soluble in about Insoluble
10 sec 10 sec
Biphenyl Insoluble Partially soluble Soluble in about
40 sec
Part B (expected results)
Compound Water Hexane
1-Octanol Insoluble Soluble
1-Butanol Partially soluble Soluble
Methanol Soluble Insoluble
Part F
In Part F, a butane torch is used to erase the gold slide. It is best that
this be done by the instructor. When erasing the slide, keep the torch moving
and do not hold it in one spot on the slide. Heating one spot for too long can
cause the slide to shatter.
ANSWERS TO QUESTIONS
1. a) yes 2. a) miscible
b) no b) miscible
c) yes c) miscible
d) no d) immiscible
e) no e) miscible
f) yes f) miscible
g) no
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© 2011 Brooks/Cole, Cengage Learning
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