Lourdes Patricia L.

Carreon Zaborah Eunice Bobadilla, Nerissa Unielle Quenga, Bernadette Toledo

February 7, 2012

Carboxylic Acids And Acid Derivatives

I. Objectives To examine the reactivities of carboxylic acids and acid derivatives via qualitative analysis II. Schematic diagram of procedure A. Solubility of Carboxylic Acids in 5% NaHCO3 1 drop glacial acetic acid + small pinch benzoic acid in two sep. micro test tubes +1 drop 0.5M NaHCO3 to each test tube record any visible change

B. Test for Acetic Acid 2 drops 2% NaOH + glacial acetic acid dropwise C. Test for Benzoic Acid 3 drops water in micro test tube + small pinch benzoic acid + 3.0 M NH4OH dropwise until solution is slightly basic to litmus +1 drop 0.1 FeCl3 soln and record any change soln slightly acid to litmus +2-3 drops 0.1 M FeCl3 solution record any observable change

heat until solid dissolves then cool

boil off excess ammonia

D. Formation of Esters From a carboxylic acid

+5 drops of ethanol + 2 drops glacial acetic acid in mictro test tube

+ 1 drop conc. H2SO4 and warm solution

note smell of product formed

From acyl halides

micro test tube with 10 drops ethanol + 2 dops of benzoyl chloride

stopper with cork and shake

note smell of product formed

E. Hydroxamic Acid Test for the ester group +1 drop ethyl acetate +1 drop ether in micro test tube +1 drop alcoholic NH2OH HCl +1 drop alcoholic KOH heat over small flame to almost boiling and then cool a little acidify with alcoholic HCl +1 drop 0.1 M FeCl3 soln

F. Hydrolysis of Acid Derivatives Acetic Anhydride +5 drops water in micro test tube +3 drops acetic anhydride moisten blue litmus paper with soln

note change in color

Esters 2 mL ethyl acetate in 10 mL round bottom flask +5 mL 25% NaOH reflux reaction mixture for 30 mins observe disappearance of pleasant sell

neutralize mixture with 6.0 M HCl

observe sour smell of carboxylic acid formed

Amides small pinch of benzamide in micro test tube

+5 drops 2% NaOH

heat solution and note odor of gas evolved

III. TABLE OF REAGENTS/PRODUCTS

Reagent/Product Glacial CH3COOH

Structure

Physical Properties

Benzoic acid

Hazards 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. Keep container closed. May be fatal if inhaled, swallowed or absorbed thru the skin Avoid all contact. Use with adequate ventilation. Wash thoroughly after use. Keep container closed.
Eye: Causes eye irritation. Causes redness and pain. Skin: May cause skin irritation. Repeated or prolonged exposure may cause drying and cracking of the skin. Ingestion: May cause irritation of the digestive tract. Inhalation: May cause respiratory tract irritation. Chronic: Prolonged or repeated skin contact may cause irritation.

5% NaHCO3

95% CH3CH2OH

Can be fatal or cause blindness if swallowed in quantity. Causes headache, dizziness, nausea, narcosis. Chronic overexposure can cause damage to gastrointestinal

Conc. H2SO4

25% NaOH

tract, liver, kidneys and cardiovascular system. Prolonged contact causes irritation to skin and eyes. 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. Keep container closed. Ingestion: Corrosive! Swallowing may cause severe burns of mouth, throat, and stomach. Skin Contact: Corrosive! Contact with skin can cause irritation or severe burns and scarring with greater exposures. Eye Contact: Corrosive! Causes irritation of eyes, and with greater exposures it can cause burns that may result in permanent impairment of vision, even blindness. Chronic Exposure: Prolonged contact with dilute solutions or dust has a destructive effect upon tissue.

0.1 M HCl

Ethyl acetate

Ingestion: Corrosive! Swallowing hydrochloric acid can cause immediate pain and burns of the mouth, throat, esophagus and gastrointestinal tract. Skin Contact: Corrosive! Can cause redness, pain, and severe skin burns. Eye Contact: Corrosive! Vapors are irritating and may cause damage to the eyes. Chronic Exposure: Long-term exposure to concentrated vapors may cause erosion of teeth. Ingestion: Causes irritation to the gastrointestinal tract. Symptoms may include nausea, vomiting and diarrhea. Skin Contact: Causes irritation to skin. Symptoms include redness, itching, and pain. Repeated or prolonged contact with the skin has a defatting effect and may cause dryness, cracking, and possibly dermatitis. Eye Contact: Causes irritation, redness, and pain.

Acetic anhydride

Ether

Causes severe irritation and burns. Harmful if swallowed. Avoid breathing vapor or dust. Use with adequate ventilation. Avoid contact with eyes, skin, and clothes. Wash thoroughly after handling. Keep container closed. Eye: Causes eye irritation. Skin: Causes skin irritation. May be absorbed through the skin in harmful amounts. Ingestion: May cause irritation of the digestive tract. Symptoms may include: headache, excitement, fatigue, nausea, vomiting, stupor, and coma. Inhalation: May cause respiratory tract irritation. May be harmful if inhaled. Exposure to high concentrations may produce narcosis, nausea and loss of consciousness. Chronic: Prolonged or repeated skin contact may cause defatting and dermatitis. Chronic exposure may cause liver damage.

10% NaOH

10% NH4OH

Ingestion: Corrosive! Swallowing may cause severe burns of mouth, throat, and stomach. Skin Contact: Corrosive! Contact with skin can cause irritation or severe burns and scarring with greater exposures. Eye Contact: Corrosive! Causes irritation of eyes, and with greater exposures it can cause burns that may result in permanent impairment of vision, even blindness. Chronic Exposure: Prolonged contact with dilute solutions or dust has a destructive effect upon tissue. Eye: Contact with liquid or vapor causes severe burns and possible irreversible eye damage. Skin: Causes severe skin irritation. Causes skin burns. May cause deep, penetrating ulcers of the skin. Ingestion: Causes gastrointestinal tract burns. Causes throat constriction, vomiting, convulsions, and shock. Inhalation: Causes severe irritation of upper respiratory tract with coughing, burns, breathing

Acetylsalicylic acid

difficulty, and possible coma. Chronic: Prolonged or repeated exposure may cause corneal damage and the development of cataracts and glaucoma. Eye: Causes eye irritation. Skin: Causes skin irritation. May be harmful if absorbed through the skin. Ingestion: Ingestion may cause high blood pressure, labored breathing, unsteady gait, lung edema, and coma. Human systemic effects include acute renal failure, acute tubular necrosis, cough, diarrhea, dyspnea (labored breathing), headache, hypermitility, nausea, vomiting, ulceration or bleeding from stomach. Toxic if swallowed. Inhalation: Causes respiratory tract irritation. Aspiration may lead to pulmonary edema. Chronic: Prolonged or repeated skin contact may cause dermatitis.

Benzoyl chloride

Ingestion: May cause irritation of the digestive tract. May cause cardiac disturbances. Inhalation: May cause respiratory tract irritation. May cause cardiac abnormalities. Inhalation at high concentrations may cause CNS depression and asphixiation. Skin: May cause skin irritation. Eyes: May cause eye irritation.

Benzamide

Ingestion: Harmful if swallowed. May cause gastrointestinal irritation with nausea, vomiting and diarrhea. Inhalation: May cause respiratory tract irritation. Skin: May cause skin irritation. Eyes: May cause eye irritation.

IV. Diagram of set-up

Figure 1. Reflux Setup v. waste disposal All aqueous solutions dilute with water and pour down the sink Organic solutions organic waste jars