Organic Compounds: Functional Group Identification WFIp2003fall

Organic Compounds: Functional Group Identification

1. How does an alcohol differ from a hydrocarbon?




2. Why do alcohols have properties intermediate between hydrocarbons and water?




3. How are esters prepared in the laboratory?




4. How are organic acids prepared in the laboratory?




5. Write the formula for the aldehyde formed from the oxidation of ethanol.




6. How can you distinguish an organic acid from an organic base?




7. Write the formula for the acid formed from ethanol s oxidation.
Organic Compounds: Functional Group Identification WFIp2003fall

8. How is an organic base similar to ammonia?




9. Write the structural formula of the functional group for each class of organic
compounds studied in this experiment.
Organic Compounds: Functional Group Identification WFIp2003fall


Perform ALL parts with an unknown sample (if provided) and record with
the known samples simultaneously.

A. Alcohols

Iodoform
1. Obtain a small sample of the alcohols listed on the Report Sheet. Dissolve 0.5
mL of each alcohol in 5 mL of H
2
O in separate 150- mL test tubes. Add 5 mL of
10% NaOH. While shaking, add drops of 10% KI/I
2
until the definite dark
yellow of iodine persists (that is, when you observe colour in the solution
mixture). Warm gently in a hot water bath; do not exceed 60C. Add more KI/I
2

at the elevated temperature until the dark yellow remains for 2 minutes. Allow
the test tube and contents to cool. While shaking, add drops of 10% NaOH to
expel excess I
2
. Half- fill the test tube with de-ionized water and allow it to stand
for 10 minutes. Look for CHI
3
, a yellow crystalline precipitate. Note any
characteristic odour. Show your products to the instructor. Whenever the amount
of alcohol is small, iodoform may not separate; however, the characteristic odour
establishes its formation. Summarize the comparative results on the Report
Sheet.

Alcohol oxidation
2. Place 2 mL of 0.1 M K
2
Cr
2
O
7
in a 150- mm test tube and slowly add 1- mL conc.
H
2
SO
4
. Swirl to dissolve the K
2
Cr
2
O
7
and cool. Prepare all testing alcohols each
in a 150-mm test tube. Simultaneously add slowly2 mL each test alcohol to the
K
2
Cr
2
O
7
solution. Note any colour change, odour and the rate of reaction.
Compare its odour with the test alcohol. Write your conclusions.

B. Aldehydes and Ketones

Tollens Test
1. To a clean 150- mm test tube, add about 1 mL of 10% NaOH solution and wash
the test tube. Then add about 1 mL of 0.1M AgNO
3(aq)
. Next add drop by drop of
NH
4
OH
(aq)
with constant shaking until the silver oxide just dissolves. Then add 1
mL of aldehyde. Repeat the same proportion with 1 mL of ketone. Warm both
test tubes in a water-bath (about 70C). Record and account the observation, and
write balance equations.

Organic Compounds: Functional Group Identification WFIp2003fall

Fehling Test
2. (optional) In a 150- mm test tube, mix about 2 mL of Potassium Sodium tartrate
(KNaC
4
H
6
O
6
) and 1 mL of Sodium hydroxide (NaOH) with 1 mL of Copper(II)
sulphate (CuSO
4
). Warm the test tubes in a water bath. Then add 1 mL of
aldehyde. Repeat the same proportion with 1 mL of ketone. Record and account
the observation, and write balance equations.

C. Acids and Bases

1. Obtain a sample of an organic acid and base. Add 0.1 g of solid (0.2 mL, that is
about 4 or 5 drops of liquid if available) to 1 mL of water in a 150-mm test tube.
Test the pH with litmus paper. If the sample is insoluble in water, add drops of
ethanol or acetone or ether until it dissolves.

2. To approximately 0.1 g of solid acid (0.2 mL, that is about 4 or 5 drops of liquid)
in a 150- mm test tube, add 2 mL of 10% NaHCO
3
. A distinct fizzing sound is
detectable even if the visual evolution of CO
2
is questionable. Record.

3. Place 2 mL of 0.1 M KMnO
4
in a 150- mm test tube and 1 mL of conc. H
2
SO
4
.
Slowlyadd 1 mL of ethanol. Watch for any colour change. Compare its odour
with that of acetic acid. What is your conclusion?

D. Esters

Banana Oil
1. Place 2 mL of glacial CH
3
COOH and 3 mL of iso-amyl alcohol, [iso-C
5
H
11
OH],
in a 150- mm test tube. Slowly and cautiously add 1 mL of conc. H
2
SO
4
. Heat
the mixture gently and carefully over a very low flame [or in a hot water bath]. If
the odour changes the product is an ester. Name it. Request the instructor to
assist you in writing the reaction s chemical equation.

Oil of Wintergreen
2. In a 150-mm test tube, place a small amount of salicylic acid, HO-C
6
H
4
-COOH,
about half the size of a pea. Add 1 drop of 3 M H
2
SO
4
and 3 drops of water.
After one-half minute add 3 or 4 drops of methanol, CH
3
OH. Place a looseplug
on the test tube and allow it to warm in a water bath at about 60C for 20 to 30
minutes. Note the odour. Request the instructor to assist you in writing the
reaction s chemical equation.
Organic Compounds: Functional Group Identification WFIp2003fall

Data
A. Alcohols
1. Iodoform Test
Alcohol Subclass
1,2,3
Observation Oxidation Product Tick if observed
for unknown
Methanol


Ethanol


i-Propanol


t-Butanol



Conclusion of observations on alcohols.






2. Oxidation of Alcohols
Alcohol Subclass
1,2,3
Observation Conclusion Tick if observed
for unknown
Methanol


Ethanol


i-Propanol


t-Butanol



Conclusion of observations on alcohols.




Organic Compounds: Functional Group Identification WFIp2003fall


B. Aldehydes and Ketones

1. Silver Mirror Reaction
Name of Compound Results of Test Tick if observed
for unknown





2. Fehling Reaction
Name of Compound Results of Test Tick if observed
for unknown





C. Acids and Bases

1. pH Test
Name of Compound Results of Test Tick if observed
for unknown





2. Sodium Bicarbonate Test
Name of Compound Results of Test Tick if observed
for unknown





3. (a) Oxidation of Alcohol
Observation: ______________________________________________________
Conclusion: _______________________________________________________


(b) Preparation of Acid
Observation: ______________________________________________________
Conclusion: _______________________________________________________
Organic Compounds: Functional Group Identification WFIp2003fall


D. Esters

1. Banana Oil
Odour of solution ___________________________________________________
Write an equation for the product s formation.
_________________________________________________________________
2. Oil of Wintergreen
Odour of solution __________________________________________________
Write the formula for the compound.





Organic Compounds: Functional Group Identification WFIp2003fall

Post-Laboratory Assignment

1. Write the structural formulas for propanol and isopropanol.




2. What reactants make the flavour characteristic of the following (refer to
instruction during the lab):
a. Pineapple


b. Orange


c. grape


3. How can you distinguish between:
a. CH
3
NH
2
and CH
3
OH


b. C
2
H
5
OH and t-C
4
H
9
OH


c. CH
3
CHO and CH
3
CH
2
OH


d. CH
3
COOH and CH
3
CHO


e. CH
3
CH
2
CHO and CH
3
CH
2
CH
2
Cl



4. Acetic acid is prepared by the oxidation of ethanol with permanganate ion in an
acidic solution. Write a balanced (redox) equation for this reaction. The reduction
product of permanganate ion is Mn
2+
.