Reactions of Alcohol

Purpose:
To identify 4 different unmarked isomers of butanol from their physical and chemical properties, observed in various tests.

Hypothesis:
Structures1:

n-butanol

s-butanol

i-butanol

t-butanol

Highest | Lowest
Part 1:

Solubility t-butanol s-butanol i-butanol n-butanol

Rate of halogenation t-butanol s-butanol i-butanol n-butanol

Rate of oxidization i-butanol n-butanol s-butanol t-butanol

In the isomers where more carbons are more evenly distributed and closer to the OH group (e.g. t-butanol), the polarizing effect of the OH is stronger whereas in structures such as n-butanol, where the OH is at the end of a long chain, the polarizing effects of the -OH are weakened. As water dissolves polar molecules better, the order of the solubility will decrease more or less according to how evenly distributed the carbon atoms are from the OH group. t-butanol will have the highest solubility, and n-butanol the lowest. Part 2: The reactivity of isomers of butanol with HCl (from the Lucas Reagent) is likely to be affected by solubility as the OH group would have to be ionized, and then displaced by Cl- ions. For this exchange, the ions in butanol would have to be dissociated. Following this logic, the reactivity of each isomer will be proportionate to its solubility in water.

Diagrams from http://en.wikipedia.org/wiki/Butanol

Sourabh Das Part 3:

25/01/2014

KMnO4 is an oxidizing agent which will react with alcohol to increase the number of bonds between C and O. Primary alcohols (n-butanol, i-butanol) will be more reactive (and form carboxylic acids), then secondary alcohols (s-butanol) which will react to form aldehydes and ketones. Tertiary alcohols (t-butanol) cannot increase the number of C-O bonds as the carbon with the OH group is attached to 3 other carbons and the 4th bond is already with an O atom. This means tertiary alcohols will not oxidize at all.

Materials:
4 Samples of unique butanol isomers 4 Test tubes 4 Test tube stoppers Test tube rack Potassium permanganate Lucas Reagent Distilled Water Graduated Cylinder Warm water bath Safety equipment

Procedure:

Part 1:
Distilled water (2mL)

Sourabh Das

25/01/2014

Part 2:
Lucas Reagent conc. HCl + ZnCl (5mL)

DO NOT SHAKE

WARM WATER BATH TO SPEED UP REACTION

Part 3:
1.0 M KMnO4 (2.0 mL)

WARM WATER BATH TO SPEED UP REACTION

Sourabh Das

25/01/2014

Observations:
Isomer Before Clear Colourless Strong odour Low viscosity Basic Test 1 Solution starts becoming cloudy at the bottom of t.t. Slow reaction 3 Colourless liquid on warm bath Clear M.P. near S.A.T.P Mild odour Basic Starts dissolving quickly 1 Some bubbling visible 2 NR 3 Low viscosity No detectable odour Basic C N.R. Basic Partially dissolved 1 NR 2 NR 3 Colourless Clear Low viscosity Mild odour Basic Frothy on shaking 1 NR 2 NR 3 Turns Brownish on heating Partially coagulates Acidic 2distinct layers NR Turns Brownish on heating Partially coagulates Acidic Separated into layers NR During After 2 visible layers Unstable emulsion visible Cloudy at the bottom Clear near the top Partial emulsification Turns reddish brown on heating Slightly acidic Fully dissolved Strong odour Emulsification visible

Sourabh Das

25/01/2014

Discussion & Evaluation: Since each compound had the same molecular formula, their masses are identical. This means that the intermolecular forces are directly influenced by their structure with no variation due to molecular size. The easiest isomer to identify was B as t-butanol as it had a very high M.P., dissolved in water quickly, and did not oxidize with KMnO4. From the 3rd test, the most complete reaction in C & D shows that they are likely to be primary alcohols, while the slower reaction of A indicates a secondary alcohol. Also the partial emulsification during the Lucas test supports that A is a secondary alcohol. i.e. s-butanol Between C and D, C is more soluble suggesting this is i-butanol. This leaves D as n-butanol. This is the final analysis of which sample was which isomer: A B C D - s-butanol - t-butanol - i-butanol - n-butanol

There were many areas which could have been improved for more accurate results. The quantity of each solution and the reactant for each test were approximated. Measuring these may allow better comparison of how fast and how well each of the samples are reacting in each test.