CHEM 40.

1 PROBLEM SET 2

1. Match the chemical tests (Column A) used for the detection of presence of functional group (Column B) and the
corresponding positive sign of reaction (Column C).
A B C
1. Benedict’s test A. peptide chain with at least 3 a. disappearance of purple color,
amino acid residues formation of brown precipitate
2. Tollens’ test B. alkenes, alkynes b. pale yellow precipitate
3. 2,4-DNP test C. sulfur-containing amino acids c. cloudiness/turbidity
4. Lead acetate test D. aldehydes, phenols d. red or purple-colored complex
5. FeCl3 test E. sugars e. brick red precipitate
6. Molisch test F. carbonyl compounds f. black precipitate
7. Lucas test G. phenols g. silver mirror
8. Iodoform test H. 2˚ methyl alcohols, methyl h. yellow orange to red orange
ketones precipitate
9. Biuret test I. carbohydrates with free i. purple complex/blue violet
anomeric C solution
10. Baeyer’s test J. 2˚ and 3˚ alcohols j. purple interface

2. Propose chemical tests to differentiate the following mixtures of compounds.

a. , ,

b. , ,

3. Differentiate the following compounds using chemical test. Indicate the positive result and the compound which
will give a positive result.

a.
b.

OH
H2N H2N
d.
c. O O
e. Glucose and lactose

4. Compound A and B have molecular formula C3H8O.

ℎ𝑜𝑡 𝑎𝑐𝑖𝑑𝑖𝑐 𝐾𝑀𝑛𝑂4
𝐴 (𝐶3 𝐻8 𝑂) → 𝐷 (𝐶3 𝐻6 𝑂2 )
ℎ𝑜𝑡 𝑎𝑐𝑖𝑑𝑖𝑐 𝐾𝑀𝑛𝑂4
𝐵 (𝐶3 𝐻8 𝑂) → 𝐶 (𝐶3 𝐻6 𝑂)
The summary of the chemical tests are in the table below:
Test A B C D
10% Na2CO3 - - - +
2,4-DNP - - + -
I2/KI, NaOH - + + -
ZnCl2/HCl - + Not done Not done
a. What are the functional groups of A, B, C and D?
b. Propose structure for A, B, C and D.