Lourdes Patricia L.

Carreon Zaborah Eunice Bobadilla, Nerissa Unielle Quenga, Bernadette Toledo

February 9, 2012

Nucleophilic acyl substitution: the synthesis of esters

I.Objective
To synthesize esters through the reversible acid-catalyzed reaction of a carboxylic acid with an alcohol (esterfication)

II. SCHEMATIC DIAGRAM OF PROCEDURE

Flavor Banana Peach Pear Pineapple Raspberry Alcohol 2-pentanol (0.6 mol) Benzyl alcohol (0.4 mol) 1-propanol (0.09 mol) Ethanol (0.09 mol) 2-butanol (0.08 mol) Volume, mL 6.54 mL + 0.3 mL 4.14 mL + 0.3 mL 6.74 mL + 0.3 mL 5.25 mL + 0.3 mL 7.36 mL + 0.3 mL Acid Acetic acid (0.06 mol) Acetic acid (0.04 mol) Acetic acid (0.09 mol) Butyric acid (0.09 mol) Formic acid (0.08 mol) Volume, mL 3.43 2.29 5.15 8.28 3.04

determine quantity of alcohol and acid needed to prepare ester

mix reactants in 25 mL round bottom flask

+boiling stones (DO NOT USE MARBLE)

cool mixture to room temperature

attach reflux condenser and allow mixture to reflux for 45-60 mins

+2-3 drops conc H2SO4 while gently swirling

pour into 30 mL separatory funnel

rinse rxn flask with cold water + washings to sep funnel

repeat until aq layer is twice the volume of organic layer

shake and allow layers to stratify

+satd NaCl soln to hasten separation

+solid NaHCO3 until acid is removed completely

ensure crude ester is clear

if mixture does not appear dry, transfer ester to a dry and clean 25 mL Erlenmeyer flask + 0.5 g Na2SO4

collect organic layer and dry with anhydrous Na2SO4

distill ester using thoroughly dried glassware

weigh ester and calculate percentage yield

determine boiling point

III. TABLE OF REAGENTS/PRODUCTS

Reagent/Product Structure Physical Propeties Hazards
Skin: May cause skin irritation. May be absorbed through the skin. Causes symptoms similar to those of inhalation. Eyes: Vapors may cause eye irritation. Contact may cause eye irritation, lachrymation (tearing), burning pain, and inflammation. Ingestion: May cause gastrointestinal irritation with nausea, vomiting and diarrhea. May cause effects similar to those for inhalation exposure.

2-pentanol

1-propanol

Eyes: May cause severe irritation, conjunctivitis, corneal burns, based on animal testing. No human information available. Ingested: May cause irritation and burning of the mouth and throat, nausea, dizziness, abdominal pain, and CNS depression. Inhaled: Vapours are irritating to the eyes, nose, throat, and respiratory tract. Severe overexposures may cause central nervous system depression with nausea, dizziness, incoordination and confusion, eventual coma and death. Hazardous in case of skin contact (irritant), of eye contact (irritant), of inhalation. Slightly hazardous in case of skin contact (permeator), of ingestion. Potential Chronic Health Effects: Slightly hazardous in case of skin contact (sensitizer). Physical State: Liquid Appearance: colorless liquid Odor: unpleasant odor - putrid odor Vapor Pressure: .43 mm Hg @20C Vapor Density: 3.0 (air=1) Evaporation Rate:Not available. Viscosity: 1.6 mPas 20 deg C Boiling Point: 162 - 165 deg C @ 760.00mm Hg Freezing/Melting Point:-7 - -5 deg C Eye: Causes eye burns. Skin: Harmful if absorbed through the skin. Causes skin burns. Ingestion: May cause severe and permanent damage to the digestive tract. Causes gastrointestinal tract burns. May be harmful if swallowed. Inhalation: May cause severe irritation of the upper respiratory tract with pain, burns, and inflammation. Causes chemical burns to the respiratory tract. Eye: Causes eye irritation. Causes

2-butanol

Benzyl alcohol

Butyric acid

redness and pain. Skin: May cause skin irritation. Repeated or prolonged exposure may cause drying and cracking of the skin.

NaHCO3

Ingestion: May cause irritation of the digestive tract. Inhalation: May cause respiratory tract irritation. Chronic: Prolonged or repeated skin contact may cause irritation. Causes severe irritation and burns. May Be harmful if swallowed. Avoid breathing vapor or dust. Use with adequate ventilation. Avoid contact with eyes, skin, and clothes. Wash thoroughly after handling. Can be fatal or cause blindness if swallowed in quantity. Causes headache, dizziness, nausea, narcosis. Chronic overexposure can cause damage to gastrointestinal tract, liver, kidneys and cardiovascular system. Prolonged contact causes irritation to skin and eyes. Corrosive, causes severe burns. Harmful by inhalation, ingestion and through skin absorption. Readily absorbed through skin. Very destructive of mucous membranes and upper respiratory tract, eyes and skin. Severe eye irritant. Inhalation may be fatal. Eye: May cause eye irritation.

Glacial CH3COOH

CH3CH2OH

Formic acid

Anhydrous Na2SO4

Conc. H2SO4

Skin: May cause skin irritation. Ingestion: Ingestion of large amounts may cause gastrointestinal irritation. Low hazard for usual industrial handling. Inhalation: May cause respiratory tract irritation. Low hazard for usual industrial handling. Causes severe irritation and burns. May be harmful if swallowed. Avoid breathing vapor or dust. Use with adequate ventilation. Avoid contact with eyes, skin, and clothes. Wash thoroughly after handling.

IV. WASTE DISPOSAL

Aqueous solutions dilute with water and pour into sink Spent drying agent trash bin Halogenated organic solvents halogenated solvents waste jar