School of the Arts, Singapore

Faculty of Science, Chemistry

Year 4

Chapter 21: Organic Chemistry – Alcohols, Carboxylic acid and

Macromolecules

Name: ……………………………………………...…. Class: B……

1. How many isomers of alcohol share the chemical formula, C4H8O?

A. 2
B. 3
C. 4
D. 5 ( )

2. Which is a secondary alcohol?

A. CH3CH2CH2OH
B. CH3CH(OH)CH3
C. (CH3)3COH
D. (CH3)2CHCH2OH ( )

3. Which statement is incorrect of ethanol, CH3CH2OH?

A. It is a primary alcohol.
B. It can be formed from ethene.
C. It is easily neutralized by aqueous NaOH.
D. It decolourises aqueous KMnO4 under appropriate conditions. ( )

5. Which statement about the compound shown is correct?

O O

C C
HO OH

A. It reacts with aqueous ammonia.

B. It dissolves in water to form a solution of pH 10.
C. It does not react with aqueous sodium carbonate.
D. It reacts readily with copper strips. ( )
6. An alcohol is oxidised to form a carboxylic acid. The carboxylic acid formed
reacts with magnesium carbonate to form (C2H5COO)2Mg and CO2. What is
the formula of the alcohol?

A. CH3CH2OH
B. CH3CH2CH2OH
C. CH3CH(OH)CH3
D. (CH3CH2)2CH2OH ( )

7. Which compound will NOT be formed when the two molecules are reacted
under appropriate conditions?

OH H OH
O O

C C H C C C H
HO OH
H H H

A. O O
H H OH
C C
HO O C C C H

H H H

B. O O
OH H H H H OH
C C
H C C C O O C C C H

H H H H H H

C. O O
H H H H H H
C C
H C C C O O C C C H

H H H H H H

D. O O O O
H H H
C C C C

HO O C C C O OH
( )
H H H
8. The repeating unit of a polymer is shown below.

H O

N C

N C
H O

Which statement of about this polymer is true?

I. It is a polyamide.
II. It is a condensation polymer.
III. It is formed from two types of monomers.

A. I and II only
B. I and III only
C. II and III only
D. I, II and III
( )

9. Propan-1-ol can be oxidized to propanoic acid in two stages.

OH I O II O

OH
propan-1-ol propanal propanoic acid

a. Explain why both stages are oxidation.

Stage I: 2H atoms are lost/ average oxidation state of C increase from -2 to -4/3
Stage II: gain 1 O atom/ average oxidation state of C increases from -4/3 to -2/3

b. State the reagent that can be used for the conversion of propan-1-ol to propanoic acid.

• Acidified potassium manganate (VII) / acidified potassium potassium dichromate (VI)

c. Propanal is the third member of the aldehyde series.
i. Write the chemical formula of the fourth member of the aldehyde series.

• CH3CH2CH2CHO/ C4H8O

ii. State the name of the fourth member of the aldehyde series.

• butanal

d. Propanoic acid reacts with methanol to from an ester.

i. Draw the full structural formula and state the chemical name of the ester formed.
H H O H

H C C C O C H

H H H

• methyl propanoate

ii. State the conditions needed for this reaction.

• Conc. sulfuric acid (as catalyst) and warm

iii. Write the full chemical equation for this reaction.

• CH3OH + CH3CH2COOH ⇌ CH3CH2COOCH3 + H2O

iv. List one use of ester.

• artificial food flavourings/ solvents

10. Parts of five polymers are shown below.

H H O O H H O O

N (CH2)6 N C (CH2)4 C N (CH2)6 N C (CH2)4 C

Polymer A

F F F F F F
C C C C C C

F F F F F F

Polymer B

O O O O

O (CH2)4 O C (CH2)2 C O (CH2)4 O C (CH2)2 C

Polymer C

CH3 CH3 CH3

O O O O O O
H C H C H C

C C C C C C

H CH3 H CH3 H CH3

Polymer D

CH2 CH2 CH2 CH2 CH2 CH2

C C C C C C
H CH3 H CH3 H CH3

Polymer E
a. Identify which are addition polymers and condensation polymers.

Addition polymer: B, D, E
Condensation polymer: A , C

b. Deduce why Polymer A is known as Nylon-6,4.

• Based on number of carbon atoms of the two monomers.

c. Polymer B is the coating in non-stick cooking pan. State the name of Polymer B.

• Polytetrafluoroethane/ PTFE

d. The average molecular mass of Polymer C is 141 000. Deduce the average number of
carbon atoms in one molecule of Polymer C.
I I I
• Repeating unit is O-(CH2O
)4-O-CO-(CH2)2-CO-
• Mr of repeating unit is about 144
I
u 172
• 979 820
Number of repeating unit is about - -

• Each repeating unit contains 8 carbon atoms W

850
• Average number of carbon atoms is -
979 x 8 = 7832
->
65608

e. Polymer D is poly(methyl methacrylate), commonly known as PMMA.

i. Draw the full structural formula of the monomer, methyl methacrylate.

O O CH3

H C

C C

H CH3
………………………………………………………………………………………………………

ii. State the full structural formula of the two compounds that can be used to produce the
monomer.
O OH

H C
H
C C
and H C OH

H CH3 H
…………………………………………………………………………………………………
 iii. PMMA is a type of acrylic (clear plastic) often used as a replacement for glass. Suggest
one advantage PMMA has over glass.
• Lighter / does not crack easily.

f. Natural rubber is made up of molecules of Polymer E. Polymer E is known as polyisoprene.

The monomer that produce Polymer E is isoprene.
i. Deduce the full structural of isoprene.
H2C CH2

C C

H CH3

………………………………………………………………………………………………………

ii. Explain if natural rubber is a suitable material to made bottles to hold bromine (aq).

• No as it is unsaturated, it will react with bromine.

iii. Natural rubber is often sent for further treatment by reacting it with sulfur. Sulfur will
“crosslink” the rubber molecules, giving the treated rubber extra strength.

Illustrate how sulfur “crosslink” molecules of Polymer E, by using three skeletal formula
of Polymer E.
 S S S

S S
S

S
S S

S S S

………………………………………………………………………………………………………
………………………………………………………………………………………………………