Name: Zhinga Steele Class: CHEM1032L2 Lab #4: Alcohols Lab Instructor: Allison Crawford Lab Partner: Matalena

Chub Lab Date: 29/ Feb/ 2012 Lab Due Date: 19/ Mar/ 2012

Alcohols Lab Exercise Objective: To investigate some of the physical and chemical properties of alcohols.

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Alcohols are the group of organic compounds that have a hydroxyl (-OH) as their functional group. The presence of the hydroxyl group has a great impact on the molecules physical and chemical properties because it provides a degree of polarity to the molecule. The influence of the polarity is stronger in smaller molecules and can be seen in the boiling points of these molecules. Presence of a polar group also affects the solubility of these compounds in water. Because the main chain is still non-polar; however, the effect of the polarity is dampened in longer chained alcohols which behave more like their corresponding alkanes.

Equipments/Materials 1ml dropper pH indicator paper 4 small test tubes Splint Warm water bath (~65C) Droppers 50ml beaker Conc. H2SO4 Conc. HNO3 Heptane Methanol Ethanol n-butanol iso-butanol tert-butanol larger alcohol (e.g. n-amyl alcohol) potassium dichromate solution Lucas Reagent

*Lucas reagent is 1 mole ZnCl2 dissolved in 1 mole concentrated HCl: it is very corrosive Exercise I (PreLab) A. Investigating physical properties of alcohols 1. Table 1 was copied and filled after researching about the compounds before the lab.

B. Physical Appearance

1. The four alcohols were Observed and the colour, state and odour was recorded. Each chemical
was wafted and not inhaled. The observation was then compared to the expectations to that of the prelab. 2. C. Solubility

1. 1 ml of water was placed into a small test tube. 2. Five drops of ethanol was added and it was shaken, then added to the tube rack 3. The steps were repeated using heptane instead of water. The appearance of the mixtures. 4. The above steps were repeated using n-butanol, iso-butanol and tert-butanol instead of
ethanol. Exercise II: A. Oxidation

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1. Four clean test tubes were labelled and then add 5 drops of the potassium dichromate solution
was added to each.

2. The color of the potassium dichromate (K2Cr2O7) was recorded. 3. Samples of ethanol was added into the first test tube. It was then Mixed thoroughly and then
gently warmed in a warm water bath. 4. The odor and color change was recorded and the above steps were repeated using n-butanol, iso-butanol and tert-butanol.

B. Esterification

1. The name of the alcohol that was used was written in the data table. 2. The odors of alcohol and ethanoic acid was recorded. 3. 10 drops of alcohol was placed in a small test tube and 10 drops of concentrated ethanoic acid
was added.

4. 6 drops of concentrated sulfuric acid was carefully added and then the mixture was warmed in
a warm water bath for 5 minutes. The contents did not boil.

5. The content of the test tube was poured into about 50 ml of water in a beaker and the odor of
the content was recorded.

6. The odor of another groups ester was compared and the odor was also recorded.

C. Lucas Test

1. 40 drops of Lucas reagent was placed in a test tube. 2. Four drops of tert-butanol was then added. It was shaken and any reaction that occurred was
noted.

3. It was then placed in a warm in a water bath for five minutes and then the changes were
recorded..

4. The above was Repeated using iso-butanol and n-butanol. Results were recorded.

DATA SHEET
Table 2: Physical appearance of alcohols Compound Ethanol n-butanol Observations Clear, colourless liquid Clear, colourless liquid

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Iso-butanol Tert-butanol Table 3: Solubility Compound Ethanol n-butanol Iso-butanol tert-butanol

Clear, colourless liquid Clear, colourless liquid

water Clear, Soluble Clear, oil-like w/ 3layers Clear, smear like: oily Insoluble w/ 2 layers

Non-polar solvent (heptane) Slightly soluble; clear almost cloudy Clear, soluble Insoluble, clear Insoluble w/ 2 layers

Table 4: Oxidation of alcohols with K2Cr2O7 With ethanol butanol Original odor Odor after adding chromate Color change Alcohol Alcohol Orange Alcohol Mild-alcohol Yellow/orange: change no

Iso-butanol Alcohol Alcohol No change: orange

Tert-butanol Alcohol dye Dark yellow

Table 5: Esterification of alcohol and ethanoic acid Substance Alcohol (Butanol ) Ethanoic acid Odor Table 6: Lucas test Alcohol Observations t-butanol Precipitate, milky; smells of glue i-butanol Nail polish smell; yellow in colour light Colourless Alcohol Pungent Vinegar-like

Reaction mixture in water Nail polish (sweet)

n-butanol Smelled sweet with a light yellow colour

Analysis Physical Properties A&B) Due to The increase in dispersion forces between larger molecules, the boiling point of alcohols increase with increasing molecular weight. Also, the melting point increases as well, when the weight increases. The Solubility of an alcohol in water depends on the amount of carbon in the compound. So compounds with short chains are very soluble in water. The solubility decreases the longer the carbon chain gets. Insoluble alcohols will form a layer at the top of the mixture. Alcohols such as tert-butanol or ethanol are similar to water so it is miscible. Alcohols with a larger organic radical are like alkanes.

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C) The combination that had mixed well was the Water with Ethanol. Also the mixture of n-butanol, iso-butnaol and tert-butanol with heptane.The reason for this being that these compounds have a small carbon chain so, the energy needed to break the bond is not great.

D) Glycerol is mainly for smoothing, lubricating and also as humectants. Glycerin helps with moisturizing, softening and soothing the skin. It is a common ingredient in lotions and soap. It typically pulls up moisture through the layers of the skin and helps with preventing dryness.

Chemical Properties A (i) 1. CH3CH2-OH+[O] K2Cr2O7 CH3HC=O+H2 Ethanol + Oxidising agent Ethanal + Hydrogen gas

2. N-butanol + Oxidising agent n-butanal + hydrogen gas 2H3CH2CH2C-OH + [O] K2Cr2O7 2H3CH2CH2CH2HC=O+2H2

3. Iso-butanol + oxidising agent K2Cr2O7 iso-butanone+hydrogen gas

2H2C-H3CH2CH2C-OH + [O] K2Cr2O7 2H2CH3C-HC=O H3C + H2

4. Tert-butanol + [o]
K2Cr2O7

no rxn

(ii)

All alcohols do not behave the same when expose to potassium dichromate due to their R-group. Alcohols with one R-group are primary alcohols producing either an aldehyde or a carboxylic group. The alcohols with 2 R-groups are secondary and therefore, produce ketones only. Alcohols with 3 R-groups are tertiary and produces nothing, because it does not react. This is due to their OH bond that is bonded to 3 carbon atoms.

(iii)

Alcohols can be oxidized naturally by exposing it to oxygen in the air or by enzymes in the liver. The most common product produced is the carbon dioxide and water. The enzymes used by the body would be Alcohol dehydrogenase or ADH, which breaks down the alcohol in the body. The other would be Catalase, which is found in the organs of peroxisomes. This enzyme metabolizes the alcohol in the brain.

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The mixture should not be boiled because it contains concentrated ethanoic acid and concentrated sulphuric acid which is highly corrosive and has a high affinity for water, which will leave a carbon residue behind. Dilution of concentrated sulphuric acid generates a lot of heat, as with acid. The smell of the product becomes more noticeable after it is mixed with water because of the previous reaction that had occurred. It produced an ester. Esters are responsible for flavour and fragrances. Esterification between a carboxylic acid and an alcohol will produce an ester and water.

Ethanol + Ethanoic acid conc. H2SO4 Ethyl ethanoate + water CH3CH2-OH+.CH3COOHconc. H2SO4 CH3COOCH2CH3+ H2O

n-butanol + ethanoic acid conc. H2SO4 n-butyl ethanoate + water H3CH2CH2CH2C-OH+ CH3COOH conc. H2SO4 CH3COOH3CH2CH2CH3+H2O

Iso-butanol+ethanoic acid conc. H2SO4 iso-butyl ethanoate + water H2C-H3CH2CH2C-OH + CH3COOH conc. H2SO4 H3C-COOH2C-H3CH2CH3C +H2O

Tert-butanol + Ethanoic acid conc. H2SO4 tert-butyl ethanoate + water

+ CH3COOH conc. H2SO4

+ H2O

5. Two uses for the ester ethyl ethanoate are nail polish removers and as an activators in paint.
6. Tert-butyl acetate is another commone ester. It is used in inks and gives out a blueberry like odor.

C Lucas Test

1. 2H3CH2CH2CH2C-OH+ZnCl22CH3CH2CH2CH2Cl+Zn(OH)2
2H2C-H3CH2CH2C-OH+ZnCl22CH2-CH3CH2CH2Cl+Zn(OH)2

+ ZnCl2 2H3CCl-CH3+Zn(OH)2

CH3

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2. The differing reactivity reflects the ease of formation of the corresponding carbocations. Tertiary alcohols react immediately with Lucas reagent as evidence by turbidity that causes the low solubility of the organic chloride in the aqueous mixture. Secondary alcohols react within about 5 or so minutes depending on their solubility. Primary alcohols do not react appreciably with Lucas reagent at room temperature. Secondary alcohols react within about 5 or so minutes depending on their solubility. Tertiary alcohols react immediately with Lucas reagent as evidence by turbidity that causes the low solubility of the organic chloride in the aqueous mixture.

Conclusion: Alcohols have different appearances. When it comes to their odor they are, to a certain extent, similar due to their strength. Some alcohols are soluble in water depending on their polarity. Esterification creates an ester group which are mostly sweet in odor.

Zhinga Steele

Pre-Lab 4

29/2/12

Table1 (Prelab): Investigation of physical properties of alcohols Group 1 Compound Ethane Propane Molecular Mass
30.07 g mol
1

Structural Formula

Melting Point
-183 C,

Boiling Point
-89 C

Relative Solubility
0.0568 g L
1

Warnings/Hazards Flammable at room temperature When like an inhalant it poses a mild asphyxiation ris k through oxygen depr ivation Hazardous in case of skin contact (irritant), of eye contact (irritant), of ingestion, of inhalation.

44.1 g mol

-188 C

-42--42 C

40 mg 1 L (at 0 C)

Ethanol

46.07 g mol

114 C

78 C

miscible

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Butane

58.12 g mol

-140--134 C

-1-1 C 61 mgL1 (at 20 C)

simple asphyxiant

1-butanol 2-butanol 2-methyl propanol 2-methyl-2- propanol

74.12 g mol

90 C

118 C

63.2 g L

-1

Irritant and flammable at 29 C Highly flammable when over heated Flammable, Irritant Flammable, irritant, asphyxiant

74.12 g mol

-115 C

98-100 C

290 g dm

74.12 g mol 74.12 g mol

108 C
25-26 C

108 C
82-83 C

95 g/L (20 C)

miscible

Decane 1-decanol

142.28 g mol 158.28 g/mol

-30--29 C 6.4 C

174-174 C 232.9 C

Insoluble Insoluble

Flammable, Irritant, Slight Narcotic Inhalation causes pneumonitis, irritant, flammable

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