Lesson 16 : Hydroxy Compounds (II)

Objective : 1. distinguish primary, secondary and tertiary alcohols by the Lucas test. 2. state the oxidation products of the different classes of alcohols. 3. explain the triiodomethane test. Activity : 1. Combustion alcohol burn in excess oxygen to form carbon dioxide and water.

C2H5OH(l) + 3O2(g) 2CO2(g) + 3H2O(l)

2. Lucas test A mixture of anhydrous zinc chloride and concentrated hydrochloric acid.

Class of alcohol Time taken for cloudiness to appear 3. 4. 5.

10 >10 min

20 >5-10 min

30 immediate

Alcohols react with the Lucas reagent to form haloalkanes. Alcohols with less than six carbon atoms are soluble in the Lucas reagent but the to form haloalkanes formed are not. The solution turns cloudy as the haloalkane is formed. When the test is carried out at room temperature, the rate at which the solution turns cloudy varied according to the type of alcohol used. Arrange the alcohol ascending time taken for the cloudiness to appear.

CH3CH(OH)CH3

CH3CH2OH

(CH3)3COH

Oxidation of alcohols 1. Primary alcohols are oxidised to aldehydes and then to carboxylic acids. Secondary alcohols are oxidised to ketones while tertiary alcohols are resistant to oxidation. Thus we can distinguish tertiary alcohols from other alcohols using acidified potassium manganate(VII) or acidified potassium dichromate (VI) ethanol 2-propanol 2-methyl2propanol No change. Oxidation only occur under vigorous condition No change. Oxidation only occur under vigorous condition

KMnO4 H+

K2Cr2O7

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Activity 2: 1. Alcohol with the structure CH3CH(OH)- gives a yellow precipitate when heated with alkaline iodine solution. 2. Add a mixture of I2 in NaOH to the test tube. Then heat. Observation : Yellow ppt formed.

CH3CH2OH + 4I2 + 6NaOH CHI3 + HCOONa + 5NaI + 5H2O

- Step 1 2NaOH + I2 NaI + NaOI + H2O -Step 2 CH3CH2OH + NaOI CH3CHO + NaI + H2O The ethanol is oxidised to ethanal which has the methylcarbonyl group. Therefore compounds with the methylcarbonyl group will also give a positive triiodomethane test.

-Step 3

CH3CHO + 3NaOI Cl3CHO + 3NaOH

-Step 4

Cl3CHO + NaOH CHI3 + HCOONa

Lets try Compound CH3OH

Triiodomethane test (Iodoform test) X

CH3CH(OH)CH3

C6H5CH(OH)CH3

CH3CH2CH2(OH)

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