Expt 15: Diels-Alder Reaction: 9,10-Dihydroanthracene-9,10-,succinic Acid Anhydride

Objective: The purpose of this experiment is to pull together everything we

did this semester, and to assess how well and how much we learned in this
course. The purpose of this experiment itself is to work with aromatic
structures, preparing us for work in Organic Chemistry II. New compounds to
us will be used, however, using tools used previously.
Experimental Procedure:
The overall experimental procedure is listed in full in Mayo on pages 269
through 273. However, changes made via modifications listed in the
Blackboard document as well as changes made in class include the following:
Via Blackboard document:

Unlike previous labs, no use of Mayo or listing of modifications will be

aloud. Work only from your written, prepared lab notes.
Your reactions yield will be turned in for credit.
Rather than as microscale, perform this experiment in a fivefold scale
(considered semimicroscale).
It is not necessary for the crude product to recrystallize.
Hand in crude product with name, TA name, section number, and
weight product.

Other modifications/error:

While heating, sand bath reached 200C, higher than it was supposed
to.
Use a plastic pipet instead of an automated pipet.
Create your own calcium tube (seal with cotton)
o Cotton Calcium sulfate Cotton

Reaction Scheme:

Data and Results:

Table:

Compound

178.24

Amount
used
(actual)
394 mg

98.06
106.16
88.11

201 mg
5.0 mL
3.0 mL

276

*theoretic
al yield:
563 mg

MW
(g/mol)

Anthracene
Maleic
Anhydride
Xylene
Ethyl Acetate
9,10Dihydroanthrace
ne-9,10-,succinic acid
anhydride

mmol

mp (C)

bp (C)

2.2

216

2.0

60
137-140
77
*recorded
262.8263.8

Observations:

With the addition of Xylene, the mixture turned an opaque, pale yellow.
When stirred, the mixture turned mildly opaque yellow.
When heated, the mixture slowly turned clear.
With the extraction, pearly, incandescent looking powdery crystals
formed.

Calculations:
1.
200 mg
x

1g
x
1000 mg

^Maleic
acid

1 mol
x
98.06 g
^MW
Maleic acid

2. Weight of watchglass + product

Weight of watchglass

276 g
x
1 mol
^MW
product

29.076 g
- 28.678 g

0.398 g or 398 mg

3.

0.398 g x 100% = 71% yield

0.563 g

1000 mg
=
1g

563 mg
product
^Calculate
d
theoretical
yield

Questions
Works Cited