Almira Delos Reyes

THUV2
Post-lab
Experiment 8: Aliphatic and Aromatic Hydrocarbons
1. Write the equations for the tests giving positive results.
Hexane
Br2: C6H14 + Br2
C6H13Br + HBr
Combustion: 2C6H14 + 19 O2
12CO2 + 14H2O
Benzene:
Tert-butyl chloride/AlCl3 :
+ AlCl3
+

+
H+

Br2: C6H6 + Br2

C6H5 + HBr
Combustion: 2C6H6 + 15 O2
12CO2 + 6H2O
2. Classify whether each of the reactions is a substitution or addition reaction.
The reaction of Hexane and benzene with Br 2 including the reaction of benzene
with AlCl3 and tert-butyl chloride are all substitution reactions. The reaction between
benzene and hexane with oxygen, on the other hand, is called combustion
reactions.
3. What are the advantages of using steam distillation in extracting limonene?
Compounds like limonene are best extracted using steam distillation because they
have high boiling point and will only decompose under high temperature needed for
them to boil. In a steam distillation, the mixture to be distilled contains mostly
water and the compound. Since most compounds like limonene are oil and are
immiscible with water, layer will be formed for easy separation. Also, the main
advantage of this distillation process is that organic compounds such as limonene
can be separated or extracted without having to heat the mixture to its boiling point
which is a rather high temperature. Heating mixtures like this in until their high
boiling point temperature would only cause decomposition or contamination with
the charring of residues that could be formed.
References:
http://infohost.nmt.edu/~jaltig/SteamDistill.pdf <Date accessed: 15 Jan 2012>
http://eppe.tripod.com/frcrfalk.htm <Date accessed: 15 Jan 2012>

Almira Delos Reyes

THUV2
Post lab
Experiment 9: Relative Rates of Electrophilic Aromatic Substitutions
1. Arrange the compounds used in the experiment in the order of increasing
reactivity towards Br2 in CH3COOH. Explain.
Chlorobenzene < Nitrophenol < Benzene < Acetanilide < Phenol < Aniline
The compounds used in the experiment are all aromatic compounds. Substituents of
these compounds are divided into two: activating and deactivating groups. Rings
that contain an activating substituent like NHCCH 3 in acetanilide, -OH in phenol or
NH2 in aniline are more reactive than benzene while rings that contain a
deactivating substituent like NO2 in nitrophenol and Cl in chlorobenzene are less
reactive than benzene.
2. Do your experiment results agree with your theoretical data? If not, what are the
possible sources of error?
No, not all results agree with the theoretical data. Several errors might have been
committed during the experiment including the way the reagents were added
together, the ability of the observer to notice the reactions and the accuracy of the
timing method used in the experiment. Also the freshness of the compounds can
affect their reactivity.
3. Predict the order of reactivity of a.) Bromobenzene, anisole, benzene, and
methylbenzoate; and b.) benzaldehyde, iodobenzene, ethoxybenzene, and toluene
towards bromination.
a.) Bromobenzene < Methylbenzoate < Benzene < Anisole
b.) Iodobenzene < Benzaldehyde < Toluene < Ethoxybenzene
4. Explain the effect of solvent in the reaction of acetanilide and Br 2 in part B.
The acetic acid in the reaction of acetanilide in Br 2 acts as a catalyst hastening the
reaction by the polarization of the hydrogen atoms of acetanilide.
Reference:
McMurry, John. Organic Chemistry. California: Brooks/Cole Publishing Company,
1984.