EXP 10: Reactions of Alcohols & Phenols

Aliphatic Alcohols

Derivatives of hydrocarbons in which a hydrogen has been replaced by a hydroxyl group

Primary

Alcohol in which OH is attached to the primary carbon atom (ex: RCH2CH2OH)

Secondary

Alcohol in which OH is attached to the secondary carbon atom (ex: R2CHOH)

Tertiary

Alcohol in which OH is attached to the tertiary carbon atom (ex: R3COH)

Dehydration of Alcohol

What is the name of (Part 1)?

Calcium Carbide (CaC2)

(Part 1) What is the name and formula of the dehydrating agent?

95%/Hydrous Ethyl Alcohol (CH3CH2OH)

(Part 1) What is the name and formula of the substance being tested?

100%/Anhydrous Ethyl Alcohol (CH3CH2OH)

(Part 1) What is the name and formula of the substance formed?

95% CH3CH2OH + CaC2 —> 100% CH3CH2OH + C2H2 + Ca(OH)2

(Part 1) What is the chemical equation of the reaction?

60 degrees celsius

(Part 1) What is the temperature the test tube has to be in for 5-10 minutes?

Test for Water in Alcohol

What is the name of (Part 2)?

95% Ethyl Alcohol (CH3CH2OH) vs 100% Ethyl Alcohol (CH3CH2OH)

(Part 2) What is the name and formula of the substances being compared?

Anhydrous Copper (II) Sulfate (CuSO4)

(Part 2) What is the name and formula of the substance added to the substances being compared?

Blue

(Part 2) What color is hydrous Copper (II) Sulfate (CuSO4)?

White

(Part 2) What color is anhydrous Copper (II) Sulfate (CuSO4)?

Intensely heating the hydrous Copper (II) Sulfate (CuSO4)

(Part 2) How is anhydrous Copper (II) Sulfate (CuSO4) obtained from hydrous Copper (II) Sulfate (CuSO4)?

Solid becomes blue

(Part 2) What occurs in the test tube containing 95% Ethyl Alcohol (CH3CH2OH) and Anhydrous Copper Sulfate (CuSO4)?

No Reaction (Solid remains white)

(Part 2) What occurs in the test tube containing 100% Ethyl Alcohol (CH3CH2OH) and Anhydrous Copper Sulfate (CuSO4)?

Solid becomes blue

(Part 2) When water is added to the test tube containing 100% Ethyl Alcohol (CH3CH2OH) and Anhydrous Copper Sulfate (CuSO4), what occurs?

Presence of Hydrogen or Water in Alcohol

(Part 2) What does the color change indicate?

Esterification

What is the name of (Part 3)?

Ester (RCOOR)

(Part 3) What is formed when an alcohol (ROH) and acid (RCOOH) are mixed together?

Ethyl Alcohol (CH3CH2OH), Acetic Acid (CH3COOH), Concentrated Sulfuric Acid (H2SO4)

(Part 3) What were the first substances mixed in esterification?

Concentrated Sulfuric Acid (H2SO4)

(Part 3) What is the catalyst added to the ethyl alcohol and acetic acid, as well as the methyl alcohol and salicylic acid?

Ethyl Acetate (CH3COOCH2CH3)

(Part 3) What is the name and formula of the substance produced as a result of the reaction between ethyl alcohol and acetic acid catalyzed by concentrated sulfuric acid?

Plastic Balloon Odor

(Part 3) What is the odor of the ethyl acetate?

Methyl Alcohol (CH3OH), Salicylic Acid (C6H4OHCOOH), Concentrated Sulfuric Acid (H2SO4)

(Part 3) What are the second substances mixed in esterification?

Methyl Salicylate (C6H4OHCOOCH3)

(Part 3) What is the substance produced by the reaction between methyl alcohol and salicylic acid catalyzed concentrated sulfuric acid?

Minty/Wintergreen

(Part 3) What is the odor of methyl salicylate?

Iodoform Test

(Part 4) What is the name of the test?

Ethyl Alcohol (CH3CH2OH)

(Part 4) What is the name and formula of the substance tested in the iodoform test?

Yellow iodoform/triiodomethane (CHI3)

(Part 4) What is the color, name, and formula of the solid formed between the ethyl alcohol (CH3CH2OH), sodium hydroxide (NaOH), and iodine (I2)?

Oxidation

(Part 5) What is the name of this part?

Ethyl Alcohol (CH3CH2OH), Isopropyl Alcohol (CH3CHOHCH3), & Tert-Butyl Alcohol ((CH3)3COH)

(Part 5) What are the alcohols that are being oxidized?

Potassium Dichromate (K2Cr2O7) & Dilute Sulfuric Acid (H2SO4)

(Part 5) What are the two substances used to oxidize the alcohols?

Orange

(Part 5) What color is potassium dichromate?

Blue-Green

(Part 5) What color does ethyl alcohol become when potassium dichromate and dilute sulfuric acid are added?

Yellow-Green

(Part 5) What color does isopropyl alcohol become when potassium dichromate and dilute sulfuric acid are added?

Orange (No Reaction)

(Part 5) What color does tert-butyl alcohol become when potassium dichromate and dilute sulfuric acid are added?

(1) Ethyl Alcohol, (2) Isopropyl Alcohol, (No Reaction) Tert-Butyl Alcohol

(Part 5) What is the oxidizing order?

Carboxylic Acid (RCOOH)

(Part 5) What is formed when a primary alcohol is oxidized?

Acetic Acid (CH3COOH)

(Part 5) What is the main product of the reaction between ethyl alcohol (CH3CH2OH), potassium dichromate (K2Cr2O7), and dilute sulfuric acid (H2SO4)?

Ketone (RCOR)

(Part 5) What is formed when a secondary alcohol is oxidized?

Acetone (CH3COCH3)

(Part 5) What is the main product of the reaction between isopropyl alcohol (CH3CHOHCH3), potassium dichromate (K2Cr2O7), and dilute sulfuric acid (H2SO4)?

None (No Reaction)

(Part 5) What is the main product of the reaction between tert-butyl alcohol (CH3CHOHCH3), potassium dichromate (K2Cr2O7), and dilute sulfuric acid (H2SO4)?

Lucas Test

(Part 6) What is the test used to distinguish between primary, secondary, and tertiary alcohols?

Replacement of hydroxyl group with halogen

(Part 6) What is replaced with what in the Lucas Test?

Hydrochloric Acid (HCl) & Zinc Chloride (ZnCl2)

(Part 6) What are the two substances added to the alcohols in the Lucas Test?

Zinc Chloride (ZnCl2)

(Part 6) What is the catalyst in the Lucas Test?

(1) Tert-Butyl Alcohol, (2) Isopropyl Alcohol, (3) Ethyl Alcohol

(Part 6) What is the order of reactions in the Lucas Test?

1-chloroethane (CH3CH2Cl)

(Part 6) What is the name and formula of the product of ethyl alcohol (CH3CH2OH) and hydrochloric acid (HCl) catalyzed by zinc chloride (ZnCl2)?

2-chloropropane (CH3CHClCH3)

(Part 6) What is the name and formula of the product of isopropyl alcohol (CH3CHOHCH3) and hydrochloric acid (HCl) catalyzed by zinc chloride (ZnCl2)?

2-chloro-2-methylpropane ((CH3)3CCl)

(Part 6) What is the name and formula of the product of tert-butyl alcohol ((CH3)3COH) and hydrochloric acid (HCl) catalyzed by zinc chloride (ZnCl2)?

Formation of an Ether

(Part 7) What is the name of this part?

Ethyl Alcohol (CH3CH2OH) & Concentrated Sulfuric Acid (H2SO4)

(Part 7) What are the reactants to form an ether in this experiment?

Diethyl Ether (CH3CH2OCH2CH3)

(Part 7) What is the ether formed as a result of the reaction between ethyl alcohol and concentrated sulfuric acid?

Dehydrating Agent

(Part 7) What is the function of the concentrated sulfuric acid?

General Anesthetic

(Part 7) What is the main use of diethyl ether?

Properties of Phenols

(Part 7.B) What is the name of this part?

0.1% Solution of Ferric Chloride (FeCl3)

(Part 7.B) What is added to the phenols?

Phenol (C6H5OH), Resorcinol (C6H4(OH)2), Salicylic Acid (C6H4OHCOOH)

(Part 7.B) What are the names and formulas of the substances ferric chloride is added?

Light Violet

(Part 7.B) What color does phenol become when ferric chloride is added?

Violet

(Part 7.B) What color does resorcinol become when ferric chloride is added?

Dark Violet

(Part 7.B) What color does salicylic acid become when ferric chloride is added?