Answer. Organic Chemistry Report.
Attached.

Laboratory Techniques in Organic Chemistry and Synthesis of 1-bromobutane (SN2 reaction)
December 10th, 2018.

Introduction.
A total of nine different laboratory techniques, for characterization (melting point, boiling point and thin
layer chromatography) or purification (recrystallization, distillation, sublimation, steam distillation, liquidliquid extraction and column chromatography) of an organic compound, were performed with the main
purpose of learn the technique by its application on a series of known and unknown chemicals. Also, some
of the techniques were applied in the synthesis of a SN2 reaction product, 1-bromobutane from sodium
bromide and 1-butanol in acidic media.
The chemical reaction involved in the different techniques and synthesis are the following:
• Liquid-liquid extraction technique.
o Acid-base properties of an organic acid, like toluic acid:
O

OH

O

O

–

+
o

Acid-base properties of an organic base, like 4-bromoanilin
+

NH3

NH2

+

+

H

Br

Br

•

+

H

Colum chromatography technique. Chemical reaction refered in the formation of the mixture that
was separated by this technique (oxidation of fluorene to 9-fluorenone):
Na2Cr2O7
CH3COOH

O

•

Synthesis of 1-bromobutane from 1-butanol (SN2 reaction)
NaBr

OH

Br

H2SO4

Calculations (only example once per different calculation).
• Recovery (used in recrystallization and sublimation). As example, recovery of phthalic acid in
the recrystallization in water.
R(%) =
•

𝑚𝑟𝑒𝑐𝑜𝑣𝑒𝑟𝑒𝑑
𝑚𝑖𝑛𝑖𝑡𝑖𝑎𝑙

× 100 =

21mg∙Phthalic acid
×
60mg∙Phtalic acid

100 = 35%

Rf (used in thin layer chromatography). As example, Rf of acetaminophen standard.
R𝑓 =

𝑑𝑠𝑢𝑏𝑠𝑡𝑎𝑛𝑐𝑒
𝑑𝑠𝑜𝑙𝑣𝑒𝑛𝑡

=

4.8cm·Acetaminophen
6.7cm·Solvent

= 0.72

Table 1. Physical Constants (Data from Dean’s Organic Chemistry Handbook)
No.
1

Name
Acetanilide

Formula
CH3CONHC6H5

mp
114.2

bp
304

Density
1.21915

2
3

Acetone
Aspirin

CH3CO CH3
HOOCC6H4OOCCH3

-95.4
135

56.24
-

0.790820
1.35

4

Anthracene

C14H10

216.3

-

1.2527

5

Benzoic Acid

C6H5COOH

122.4

132.5

-

Biphenyl
4-Bromoaniline
1-Bromobutane
1-Butanol
1-Butene
4-Chloroaniline
2-Chlorobenzoic
Acid
Cinnamic Acid
Citral
Cyclohexane

C6H5-C6H5
BrC6H4NH2
CH3CH2CH2CH2Br
CH3CH2CH2CH2OH
CH3CH2CH=CH2
ClC6H4NH2
ClC6H4COOH

68.8
66.3
-112
-88.6
-185
72.5
142

255.0
101.6
117.7
-6.3
232
-

0.993970
1.4970100
1.268525
0.809720
0.626-185
1.16977
1.54425

C6H5CH=CHCOOH
C10H16O
C6H12

134
6.5

300
229
80.7

1.24754
0.886920
0.778620

Dibutyl Ether
1,4Dichlorobenzene
Ethanol
Ethyl Acetate
Ethyl 4Aminobenzoate
Fluorene
9-Fluorenone
Hexane
Maleic Anhydride

C4H9OC4H9
C6H4Cl2

-97.9
53

142.4
174.1

0.768920
1.241760

CH3CH2OH
CH3COOC2H5
H2NC6H4COOC2H5

-115
-84
88-90

78.3
77.1
310

0.789420
0.900620
-

C13H10
C13H8O
CH3(CH2)4CH3
C4H2O3

114.8
82-85
-95.4
52.8

295
342
68.7
202.0

1.2030
1.130099
0.659420
1.48

CH3OH
(CH3)3COH

-97.7
25.8

64.7
82.4

0.791320
0.785820

27

Methanol
2-Methyl-2propanol
Naphthalene

C10H8

217.7

1.16220

28
29
30

1-Naphthol
Neral
2-Phthalic Acid

C10H7OH
C10H16O
C6H4(COOH)2

288
229
-

1.095499
0.888820
1.59320

vs alc, bz, chl, eth
misc alc, eth, glyc
0.6aq, 10alc, 0.5eth, vsls chl

31

Toluene

C6H5CH3

80.2
subl
96
206208
-95

110.6

0.866020

32

4-Toluic Acid

CH3C6H4COOH

Urea

(H2N)2CO

274275
d>mp

-

33

180182
132.7

misc alc, chl, eth, acet,
HOAc
vs alc, eth

6
7
8
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24

25
26

1.3218

Solubility
0.56aq, 29alc, 2bz, 27chl,
25acet, 5eth.
misc aq, alc, chl.
0.33aq, 20alc, 5.9chl, 5eth,
sls bz.
i aq, 1.5alc, 1.6bz, 1.2chl,
3.1CS2
0.29aq, 43alc, 10bz, 22chl,
33eth, 33ac...