Experiment 1. Solubility Of Organic Compounds 551349

Jeanette Vivien R. Jalalon Performed: Lab Partner:

Date

Experiment 1 Solubility of Organic Compounds I. Objectives(s) 

To determine the solubility class of organic compounds using solvent systems in order to determine their main functional group

II. Schematic Diagram of the Procedure Add 5 drops solvent to micro test tubes

Add 1-2 drops/pinch test compound, shake; fresh sample

+ H2O

III. Table of Reagents/Products (MSDS) + diethyl ether

S1

S2 (highly polar

+ 5% NaOH

+ 5% HCl

+ 5% NaHCO3

Water-soluble compounds B Reagent or Product Acetone

A2 (weak)

A1 (strong)

Basic Physical Hazards Waste Acidic compounds Properties Disposal compounds M + conc (MP, BP, Density, H2SO4 Appearance, etc) Miscellaneous (CH3)2CO neutral Melting Point: skin and non-95C (-139F) eye irritant, halogenated compounds BoilingI Point: organic waste N carcinogeni 56.5C (133F) c, Inert compounds Neutral compounds hazardous when ingested. Structure

Density: 0.7845 Appearance: Clear, colorless, volatile liquid.

Aniline

C6H5NH2 Melting Point: -6.2C (21F) Boiling Point: 184C (363F) Density: 1.022 Appearance: Colorless, oily liquid. Darkens on exposure to light or air.

combustible , carcinogeni c, irritant, permeator, hazardous when ingested

nonhalogenated organic waste

Benzaldeh yde

C7H6O

Melting Point: -26C Boiling Point: 179C Density: 1.04 Appearance: slightly soluble in water

eye and skin irritant, permeator, hazardous when ingested

nonhalogenated organic waste

Benzamid e

C7H7NO

Melting Point: 127 - 130C (261 266F) Boiling Point: 288C (550F) Density: 1.314 Appearance: Colorless crystals.

irritant, permeator, very hazardous in case of ingestion

nonhalogenated organic waste

Benzoic Acid

C6H5COOH

Melting Point: 122C (252F) Boiling Point: 249C (480F) Density: 1.2659 Appearance: White, needle-like crystals.

eye and skin irritant, permeator, hazardous when ingested

nonhalogenated organic waste

Benzyl Alcohol

C6H5CH2OH

Melting Point: -15C (5F) Boiling Point: 205C (401F)

slightly hazardous when

nonhalogenated organic

Density: 1.04 Appearance: Clear, colorless liquid.

ingested, skin and eye irritant

waste

Ethanol

C2H6O

Melting Point: -114 Boiling Point: 78C Density: 0.789 Appearance: Clear, reddish brown liquid.

sensitizer, skin and eye irritant, permeator, do not inhale

nonhalogenated organic waste

Hexane

C6H14

skin and eye irritant, permeator, flammable

nonhalogenated organic waste

Phenol

C6H6O

Melting Point: ca. -95C (ca. -139F) Boiling Point: ca. 68C (ca. 154F) Density: 0.66 Appearance: Clear, colorless liquid. Melting Point: 43C (109F) Boiling Point: 182C (360F) Density: 1.07 Appearance: Colorless to light pink crystals.

corrosive, irritant, sensitizer, permeator, may produce blistering,

nonhalogenated organic waste

Sucrose

C12H22O11

Melting Point: 160 - 186C (320 367F) Density: 1.587 Appearance: Monoclinic sphenoidal crystals.

eye irritant, slightly hazardous in case of

nonhalogenated organic waste

Tert-butyl chloride

C4H9Cl

Melting Point: -26C Boiling Point: 127.0 - 129.0 deg C @ 760.00m Density: 0.84 Appearance: Clear

flammable, do not induce vomiting, hazardous when

halogenated organic waste

liquid

ingested

Toluene

C7H8

Melting Point: -95C (-139F) Boiling Point: 111C (232F) Density: 0.867 Appearance: Clear, colorless liquid.

flammable, irritant, hazardous when ingested

nonhalogenated organic waste

Diethyl ether

C4H10O

Melting Point: -123C (-189F) Boiling Point: 35C (95F) Density: 0.7137 Appearance: Clear, colorless liquid.

irritant, permeator, flammable

nonhalogenated organic waste

5% NaOH

NaOH

Melting Point: 318C (604F) Boiling Point: 1390C (2534F) Density: 2.13 Appearance: White, deliquescent pellets or flakes.

corrosive, permeator, do not induce vomiting

base waste

5% NaHCO3

NaHCO3

Melting Point: 60C (140F) Boiling Point: 851C Density: 2.159 Appearance: White crystalline

slightly hazardous when ingested, skin and eye irritant

base waste

powder. 5% HCl

HCl

Conc. H2SO4

H2SO4

Melting Point: -74C (-101F) Boiling Point: 53C (127F) Azeotrope (20.2%) boils at 109C (228F) Density: 1.19 Appearance: Colorless, fuming liquid Melting Point: 3C (100%), -32C (93%), -38C (78%), -64C (65%). Density: 1.84 Appearance: Clear, colorless solution.

corrosive, permeator, irritant, sensitizer

acid waste

very corrosive, irritant, may produce tissue damage

acid waste

IV. Set-ups (if any) Materials and Apparatus 

Micro test tubes, Pasteur pipette, spatula

Waste Disposal  

Dilute all aqueous solutions and pour to the sink with copious running water. Dispose the undissolved solids to the SOLID WASTE container. Transfer all heterogenous solutions to a separatory funnel. Collect the awueous layer and pour to the sink with copious running water. Dispose the organic layer to the NONHALOGENATED ORGANIC WASTE jar.

V. Data

Guide Questions 1. For solutes that are dissolved because of intermolecular attractions with the solvent, state the intermolecular forces of attraction involved. a. b. c. d. e.

Sucrose - water: Hydrogen bond Ethanol - water: Hydrogen bond Ethanol - diethyl ether: London dispersion forces Acetone - water: Hydrogen bond & Dipole-dipole forces Acetone - diethyl ether: London dispersion forces

2. For solutes that are dissolved because of reaction with the solvent, write the balanced equations involved. a Benzoic acid – 5% NaOH C6H5COOH(s) + NaOH(aq) → C6H5COO-Na+(aq) + H2O(l) b Benzoic acid – 5% NaHCO3 C6H5COOH(s) + NaHCO3(aq) → C6H5COO-Na+(aq) + H2CO3(g) c Benzyl alcohol – concentrated H2SO4 C6H5CH2OH(l) + H2SO4(aq) → C6H5CH2OH2+(aq) + HSO4-(aq) d Benzaldehyde – concentrated H2SO4 C6H5CHO(l) + H2SO4(aq) → C6H5COH+(aq) + HSO4-(aq) e Phenol – 5% NaOH C6H5OH(s) + NaOH(aq) → C6H5ONa(aq) + H2O(l) f Aniline – 5% HCl C6H6NH2(l) + HCl → C6H6NH3+Cl-(aq) + H2O(l) 3. On the basis of solubility behavior, determine the best solvent to differentiate the following pairs of compounds. a. CH3COOH and CH3(CH2)5COOH (H2O) b. CH3CH2OCH2CH3 and CH3CH2OH (diethylether) c. Toluene and benzaldehyde (H2SO4) d. Tert-butyl chloride and tert-butanol (H2SO4) a CH3COOH and CH3(CH2)5COOH  Water: CH3COOH is soluble in water while CH3(CH2)5COOH is not because it has more than 5 carbons in its parent chain b CH3CH2OCH2CH3 and CH3CH2OH  Water: CH3CH2OH is soluble in water while CH3CH2OCH2CH3 is not because it is a non polar molecule c toluene and benzaldehyde  concentrated H2SO4: benzaldehyde is soluble in concentrated H2SO4 while toluene is not because it will not react with the solvent d tert-butyl chloride and tert-butanol  water: tert-butanol is soluble in water while tert-butyl chloridebecause they do not have the same intermolecular force References 1 M. Jones and S.A. Fleming, "Organic Chemistry", Norton, 4th edn., pp1416. 2 Chemistry Online. (n.d.). Solubility. Retrieved January 28, 2015 from http://webapps.utsc.utoronto.ca/chemistryonline/solubility.php 3 Clayden, J (2001). Organic Chemistry. OxfordUniversity Press

4 Gilbert, J. (2011).Experimental Organic Chemistry: A Miniscale and Microscale Approach. Boston, MA: Cengage Learning 5 Lehman, J. (2008) Operational Organic Chemistry: A Problem-Solving Approach to theLaboratory Course. Prentice HallShriner, R. (2004).The Systematic Identification of Organic Compounds. Canada: John Wiley &Sons.