Santos, Clarice March 9, 2019

EXPERIMENT 8: ALIPHATIC AND AROMATIC HYDROCARBONS

ANSWERS TO QUESTIONS

1. Write the equations for all the tests that gave positive results. Classify whether the reaction is a
substitution or addition reaction.
A. Electrophilic Aromatic Substitution
a) Limonene - color change from clear to yellow solution

B. Free Radical Substitution: Br2 in light

a) Hexane

b) Limonene

+ +

+ +

C. Electrophilic Addition
a) Br2 in dark: Limonene

B) KMnO4: Limonene

2. What are the advantages of using steam distillation in extracting limonene?

Steam distillation is a common laboratory technique used is extracting oils from natural
materials like essential oils from plants. It can distill insoluble mixtures in the presence of steam
that makes the compound boil at a lower temperature. Limonene decomposes at high
temperature that is why it is better to steam distill.
References
McMurry, J. (2015). Organic Chemistry 9th ed. Brooks/Cole, Cengage Learning: Belmont.

Zubrick, James W. The Organic Chem Lab Survival Manual: a Students Guide to Techniques.
9th ed., Wiley, 2012. p.18.
Organic Chemistry Laboratory Manual

Name: _Clarice Santos__________________

Groupmate: _Alpecho, Tiampong__________ Date Performed: _2.27.2019___________
Section: ___WFR____________________

EXPERIMENT 8. ALIPHATIC AND AROMATIC HYDROCARBONS

A. Isolation of Limonene

Limonene Source orange peels

Weight of raw source, g 160.96 g
Volume of limonene extract, mL
Weight of limonene extract, g
Density, g/mL (MSDS)
%% yield

B. Physical Properties of Hydrocarbons

Solubility in Density Compared

Hydrocarbon Physical State Color
Water to Water
Hexane liquid clear insolub le 0.659 g/ml

Limonene liquid clear insolubl e 0.842 g/ml

Toluene liquid clear insolubl e 0.87 g/ml

C. Chemical Properties of Hydrocarbons

Hydrocarbon t-BuCl/AlCl3 Br2, light Br2, dark I2 in KI KMnO4 Combustion

Purple/ Orange,
Dark Dark orange/ Blue flame/
Hexane NVR orange orange yellow NVR White smoke

Orange
Orange/ Clear soln/ flame/ black
Limonene yellow clear clear yellow Black ppt smoke

Pink/ Orange
Light Orange/ flame/ black
Toluene NVR orange yellow yellow NVR smoke