Lourdes Patricia L.

Carreon Zaborah Eunice Bobadilla, Nerissa Unielle Quenga, Bernadette Toledo

January 5, 2012

Alipathic and Aromatic Hydrocarbons

I. Objective
To isolate limonene as a pure compound via steam distillation To determine the physical and chemical properties of hexane, limonene, and benzene

II. Schematic Diagram of Procedure

A. Isolation of Limonene collect amt enough to fill half of a 500 mL round bottom flask steam mixture until there is about 100 mL of distillate

prepare steam distallation setup

cut citrus sample to small pieces

weigh and +250 mL water into the flask

+ 3-5 mL satd NaCl soln to distillate and let it stand

pipette out all limonene that will float on the surface

+ spatula-full of anhydrous Na2SO4 to mixture to dry it (add another if it clumps)

swirl mixture

+ more drying agent if necessary

B. Physical Properties of Hydrocarbons

Note: Physical state Color Solubility in water Density Compare to water of hexane, limonene, and benzene

Record observations

C. Chemical Properties of Hydrocarbons

1 drop of hexane, limonene, and benzene into separate micro test tubes + 2 drops tert-butyl chloride to each test tube incline test tube and place small crystal of anhydrous AlCl3 near its
mouth

mix thoroughly

stopper test tube and make sure crystal does not fall into soln

let soln wet crystal and observe change in color

repeat procedure for all solns

2 drops each of hexane, limonene, and benzene in micro test tubes

+ 1 drop 0.05 Br2 in H2O in each test tube

shake well and record observations

2 drops of hexane, limonene, and benzene in micro test tubes

+ 2 drops .0005 M KMnO4 soln

shake well and record observations

ignite 5 drops each of hexane, limonene, and benzene in evaporating dishes

observe char of flame (clear of sooty)

record observations

III. Table of Reagents/Products

Reagent/Product Structure Physical Properties Hazards
Breathing vapors may cause drowsiness and dizziness. Causes eye, skin, and respiratory tract irritation. May be harmful if absorbed through the skin. Aspiration hazard if swallowed. Can enter lungs and cause damage. Possible risk of impaired fertility. Long-term exposure may cause damage to the nervous system of the extremities. Slightly hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation.

n-hexane

NaCl

Benzene

The substance is toxic to blood, bone marrow, central nervous system (CNS). The substance may be toxic to liver, Urinary System.

Tert-butyl chloride

nausea, vomiting, stomach pain, difficulty breathing, symptoms of drunkenness, convulsions, coma

Anhydrous Na2SO4

Hazardous in case of eye contact (irritant). Slightly hazardous in case of skin contact (irritant), of ingestion, of inhalation. Liquid or spray mist may produce tissue damage particularly on mucous membranes of eyes, mouth and respiratory tract. Skin contact may produce burns. Inhalation of the spray mist may produce severe irritation of respiratory tract, characterized by coughing, choking, or shortness of breath. Severe over-exposure can result in death. Eye contact can result in corneal damage or blindness. Skin contact can produce inflammation and blistering. Inhalation of dust will produce irritation to gastro-intestinal or respiratory tract, characterized by burning, sneezing and coughing. Severe over-exposure can produce lung damage, choking, unconsciousness or death.

Br2

AlCl3

IV. Set-up

Figure 1. Simple Distillation Set-up