PRACTICE MODUL SK025 2nd Edition

PRACTICE MODULE CHAPTER 6 SK025

5. What is the accepted current view of the model for bonding in benzene?
A. Delocalised model
B. Resonance structure
C. Kekulé structure
D. Arrhenius structure

6. Which is the correct drawing of 2-bromonitrobenzene?

A. NO2 B. NO2

Br

Br D. NO2
Br Br
C. NO2

Br

7. Which is the correct drawing of 4-phenyl-1-butene?
A. B.

C. D.

8. O O

CH3 C Cl CH3

AlCl3

The reaction is known as
A. Alkylation
B. Acylation
C. Chlorination
D. Tautomerism

9. What will be the product formed when benzene reacts with Br2 in CCl4 medium?
A. bromobenzene
B. 1,2-dibromobenzene
C. 1,2-dibromocyclohexane
D. None of the above

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PRACTICE MODULE CHAPTER 6 SK025

10. Choose the correct statement about the given reaction.

? NO2

C6H6

A. conc. HNO3 + conc. H2SO4
B. HCl + CO + AlCl3
C. Cl2, FeCl3
D. NH3

11. Which of the following act as catalysis in the nitration of benzene?
A. conc. HNO3
B. FeCl3
C. conc. H2SO4
D. dilute H2SO4

12. The reaction in which benzene reacts with alkyl halide in the presence of a Lewis acid as a
catalyst to produce alkylbenzene is known as ___________
A. Acetylation
B. Halogenation
C. Friedel-Crafts Acylation
D. Friedel-Crafts Alkylation

13. The following are the reaction involved in benzene except
A. Nitration
B. Halogenation
C. Hydrohalogenation
D. Friedel-Crafts Alkylation

14. Name the type of reaction involved when nitronium ion attacks the electrons of the aromatic
ring of benzene.
A Nucleophilic addition
B Electrophilic addition
C Electrophilic substitution
D Free radical substitution

15. The species that attacks the benzene molecule in the nitration of benzene using a mixture of
concentrated nitric and concentrated sulphuric acid at 50-55oC is
A NO3-
B NO2+
C NO3+
D NO2

16. The reaction of benzene with a mixture of concentrated sulphuric acid and concentrated
nitric acid produced nitrobenzene. Which of the following statement best describes function
of concentrated sulphuric acid?
A To remove water molecules
B Act as acid catalyst to protonate nitric acid
C Act as a solvent
D To form unstable complex with benzene

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PRACTICE MODULE CHAPTER 6 SK025

17. Methylbenzene can be prepared by reacting benzene and chloromethane in the presences
of FeCl3 (as catalyst). The electrophile responsible for the attack of the aromatic benzene
ring is
A Cl+
B Cl-
C CH3+
D CH3-

18. The only compound that will yield benzoic acid when reacted with acidified potassium
dichromate (VI) solution.
A CH2=CH2
B C6H10
C C6H5C(CH3)3
D C6H5CH(CH3)2

19. + Br2 FeBr3 chloroethane
AB

AlCl3

What is/are the structures of B? B Br
A Br

CH2 CH3 Br

C Br Br D Br Br

CH2CH3 Br

+ +

CH2CH3

20. C6H6 CH3CH2Br Br Cl2 CC
A AlBr3 FeCl3
AA K2Cr2O72 /H+ BB
Structure of CC is ….
B COOH
COOH
Cl

Cl

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C CH2CH3 PRACTICE MODULE CHAPTER 6 SK025
D Cl

Cl

A B CH2CH3 D
I only I & II I, II, & III
C
II & III

21. Which of the following compound is/are aromatic compound(s)?
I

II

III +

Answer:
22. Which of the compounds can react with an alkaline solution of potassium

permanganate(VII)?
I

II

III

Answer:

WORKSHEET 6.5
MODEL OF PSPM QUESTIONS

1. An aromatic compound G, C9H12,is prepared through the reaction of benzene with reagent
J in the presence of anhydrous aluminium chloride at room temperature. G reacts with hot
acidified potassium dichromate(VI) solution produces H, C7H6O2.
(a) Suggest the structures of G, H and reagent J.

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PRACTICE MODULE CHAPTER 6 SK025
(b) State the function of anhydrous aluminum chloride in the formation of G.
(c) G undergoes bromination in the presence of light. Write the reaction equation and
state the type of the reaction.
2. Compound S is formed when benzene reacts with 2-bromopropane in the presence of AlBr3.
Chlorination of S in light gives two monochlorinated compounds, T (major product) and U.
When S is treated with acidified solution of KMnO4, compound V is formed. Draw the
structures of S, T, U and V. Name the reaction for the formation of S and write its
mechanism.

Prepared by : Mdm Nur Zarifah Syazana
Checked by : Mdm Norihan

148

PRACTICE MODULE CHAPTER 7 SK025

CHAPTER 7 : HALOALKANE

NaOH (aq)

H2O

CH3CH2OK

Haloalkane CH3CH2OH H3O+

Alkane

Type Of Reaction: NaCN, alcohol i) CH2O 10 Alcohol
Nucleophilic  ii) H3O+ 20 Alcohol
Substitution 30 Alcohol
CH3COONa i) CH3CHO Carboxylic Acid
ii) H3O+
Mg Grignard
dry ether reagent i) CH3COCH3
ii) H3O+
KOH, ethanol
reflux i) CO2
ii) H3O+
NH3 (excess)


CH3 CH2NH2


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PRACTICE MODULE CHAPTER 7 SK025
7.1 : INTRODUCTION TO HALOALKANES
WORKSHEET 7.1
For each haloalkane write the IUPAC name.

a) CH3CH2CH2CH2I

b) CH3
CH3CH CH2CH2 Cl

CH3
Br CH2 CH2 CH2C CH2Br
c) CH3

CH3
CH3C CH2CH2 Cl
d) Cl

I CH2 CH2 Cl
e) CH3 CH CHCH2 CH3

Br Cl
f) CH3 CH CH2 CH2 CH CH3

g) (CH3)3CCl

h) (CH3CH2)2CHCI

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PRACTICE MODULE CHAPTER 7 SK025

i) .

I

CH3
j) Cl

WORKSHEET 7.2
Draw the structural formula for the following molecules.
1. 2- chloro-3,3-dimethylhexane -

2. 3,3-dichloro-2-methylhexane -
3. 3-bromo-3-ethylpentane -

4. 1,1-dibromo-4-isopropylcyclohexane -
5. 4-sec-butyl-2- chlorononane -

6. 1,1-dibromo-4-tert-butylcyclohexane

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PRACTICE MODULE CHAPTER 7 SK025

WORKSHEET 7.3
Classify the haloalkane below.

Br
C H3C HC H2C HC HC H2C H3

a) CH3 CH3

b) CH3
Cl

c)

CH3
CH3CH CH2CH2 Cl

d)

(CH3)3CCl

WORKSHEET 7.4
1. What is meant by SN1 and SN2?

SN1:
SN2:

2. Give three differences between SN1 and SN2 reactions. SN2
SN1

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PRACTICE MODULE CHAPTER 7 SK025

7.2 CHEMICAL PROPERTIES OF HALOALKANES
WORKSHEET 7.5
Draw the products of each the reactions below.

1. CH3CH2CH2CH2Cl + NaOH

2.

CH3CH2Cl + NH3 ethanol

(excess)

3.

I + NaCN

reflux

4. Cl
+ H3C C O-
O

5.

I + H2O

6. CH3 + CH3CH2OH
Cl

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PRACTICE MODULE CHAPTER 7 SK025

7. Cl
+ NaOCH3

8. CH2CH2Cl
ethanol

+ KCN
reflux

9. CH3 + KOH (aq)
CH3CH2 C Cl

CH2 CH3

10.

Br KOH /ethanol
reflux

11.

Br

CH3CH2ONa

CH3 CH2 CH CH3

CH3CH2OH, reflux

WORKSHEET 7.6
1. Write the mechanism of the following reaction and label the rate - determining step:

a) Cl + KOH OH + KCl
CH3 C CH3
CH3 C CH3
CH3 CH3

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PRACTICE MODULE CHAPTER 7 SK025

Answer:

b) CH3 CH3 + NaBr
Br + NaOH (aq)
OH

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PRACTICE MODULE CHAPTER 7 SK025

c) CH2 OH
CH2Cl
+ NaOH

+ NaCl

WORKSHEET 7.7 -

1. Arrange the following haloalkane according to increasing reactivity towards SN1 mechanism.

CH2 Br CH3

CH3 Br

Br

Br

ANSWER:

2. Arrange the following primary haloalkane towards decreasing reactivity towards SN2
mechanism.
1-bromopentane, 1-bromo-2-methylbutane, 1- bromo-2, 2 -dimethylpropane
ANSWER:

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PRACTICE MODULE CHAPTER 7 SK025

WORKSHEET 7.8
Fill the gaps with the suitable products.

1. H3O+

Br + Mg
dry ether

2. + HCHO H3O+

CH3CH2Br + Mg + CH3CHO H3O+
dry ether + CH3COCH3 H3O+

3. + CO2
H3O+
CH2 Cl
+ Mg

dry ether

4.

CH3Br + Mg
dry ether

5.

CH3CH2CH2Br + Mg
dry ether

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PRACTICE MODULE CHAPTER 7 SK025

WORKSHEET 7.9

MULTIPLE CHOICE QUESTIONS

Answer ALL the questions

1. Which of the following compound is formed when 1-bromobutane is refluxed with aqueous sodium
hydroxide?

A. CH3CH2CH2CH2ONa B. CH3CH2CH=CH2

C. CH3CH2CH2CH2OH D. CH3CH2CH2COONa

2. Which of the following compounds is least likely to be hydrolysed by aqueous sodium hydroxide?

A. (CH3CH2)3CCl B.
Cl

C. (CH3)2CHCl D. CH2CH2Cl

3. P KOH, ethanol C4H8 KMnO4/H+ CH3CH2COOH +CO2 + H2O




P could be:

A. CH3CH2CH2CH2I B. CH3CH2CHICH2I
D. (CH3)2CHCH2I
C. CH3CHICHICH3
CH3CH2 CH2 CH2NH2
X
B. excess ammonia
4. CH3CH2 CH2 CH2I D. potassium cyanide

X is

A. ammonium chloride

C. conc. nitric acid

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PRACTICE MODULE CHAPTER 7 SK025

5. For which of the following compounds is the rate of alkaline hydrolysis is independent of the
concentration of the hydroxide ion?

A . CH3CH2CH2CH2I B. CH3 CH CH3
C. CH2CH2Cl Br

D. (CH3)3CBr

6. Which of the following does not react with bromoethane?

A. water B. ammonia

C. potassium cyanide D. potassium manganate (VII)

7. The alkaline hydrolysis of (CH3)3CBr involves two steps:

(CH3)3C Br (CH3)3C + + Br -

(CH3)3C + + OH - (CH3)3C OH

Which of the following is the rate equation for the above reaction?

A. rate = k [OH -]

B. rate = k [(CH3)3C Br]
C. rate = k [(CH3)3C+ ]
D. rate = k [(CH3)3C Br ] [ OH -]

8. The rate of SN1 reaction is the fastest in the hydrolysis of
A. 1-bromopropane

B. 2-bromopropane

C. 2-bromo-2-methylpropane

D. 1-bromo-2,2-dimethylpropane

9. Which of the following is a false statement about haloalkanes?

A. Haloalkanes have higher boiling point than alkanes of the same molecular mass.
B. In dry ethereal solutions, both alkyl and aryl halides react with magnesium to

form Grignard reagents.
C. Haloalkanes undergo elimination reaction when react with aqueous solution

of potassium hydroxide.
D. Alkyl fluorides are seldom used in nucleophilic substitution because they react

so slowly.

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PRACTICE MODULE CHAPTER 7 SK025

10. 2-bromo-2-methylbutane reacts with KCN to form X. What is the name of that
reaction mechanism? State the order of the above reaction.

A. SN1 and first order reaction
B. SN2 and second order reaction
C. SN1 and second order reaction
D. SN2 and first order

ABCD

I only I and II II and III I, II, and III

11. Choose the true statement about SN1 mechanism.

I. SN1 is first-order reaction.
II. SN1 is favoured by tertiary haloalkane.
III. SN1involves the formation of carbocation as intermediate.

Answer:

12. A certain reaction mechanism is shown below:

HO- + H H H
C HO C
H3C Br H3C Br HO C + Br-
H H
CH3

H

Which of the following is/are true regarding the mechanism?
I. The reaction is SN2
II. The rate of reaction depends on the concentrations of OH- and CH3CH2Br.
III. The alcohol produced is optically active.
Answers:

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PRACTICE MODULE CHAPTER 7 SK025

13. Choose true statement for SN2 mechanism.

l. The reaction involves the formation of a transition state.
ll. The reaction occurs in 2 steps.
lll. The reaction rate only depends on the concentration of substrate.

ANSWER:

WORKSHEET 7.10
MODEL OF PSPM QUESTIONS (2 0R 3 QUESTIONS FROM PAST YEAR)
1. Compound C reacts with reagent D to give unsaturated compounds, E and F.

CH3 reagent D
Cl
E+F

Compound C

i. Draw the structures of E and F. Label the major product
ii. Explain how the major product is determined.
iii. State reagent D.
iv. What is the function of D? Explain your answer.

[8 marks]

2. The reaction of an alkyl halide, X, with sodium methoxide, NaOCH3, produces 1- methoxybutane.
Using a suitable justification, propose the structure of X. Write the mechanism for the formation of
1- methoxybutane. Name this mechanism. If sodium methoxide is replaced with methanol,
what is its effect on the rate of reaction above? Explain your answer. Give another factor that
influences the rate of reaction.
[10 marks]

3. An alkyl bromide EE reacts with CH3CH2OH to give FF, whereas compound
C H3COOCH(CH3)CH2CH3 is formed when EE is treated with a nucleophile.
Dehydrohalogenation of EE produces GG which obeys Saytzeff’s rule.
Deduce the structures of EE, FF, GG and nucleophile. Write reaction equation for all
reactions involved.
[10 marks]

Prepared by Mdm Suhaina Binti Mohd Yatim
Checked by : Mdm Norihan & Mdm Nurul Azwa

161

PRACTICE MODULE CHAPTER 8 SK025

CHAPTER 8: HYDROXY COMPOUNDS

WORKSHEET 8.1 NOMENCLATURE

• Draw
• Classify
• Name

Complete the table. Give IUPAC name Class of alcohol
Draw structure
Aliphatic/ Aromatic
1. CH3CH2CH2CH2CH2OH 1o/ 2o/ 3o

2. CH3CH2CH(CH3)CH2OH

3. CH3CH(OH)CH2Cl

4. HOCH2CH2CH2OH

5. CH3CH(OH)CH2CH2CH2CH3

6. (CH3)3COH

7. OH
CH3 Br

8.
CH2CH3

CH3 CH CH CH2CH2
OH

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9. PRACTICE MODULE CHAPTER 8 SK025
HO CH3
OH
10.
HO

11. CH3 OH

CH3C CH2 CH2 CH CH2

CH3 Cl

12.
HO

Cl

13. CH3 CH2CH2OH
C C

H H

14. CH3
HO

15. CH3 OH

CH3CH CH2 CH2 CH CH3

16. OH
CH2CH CH2 CH2
Cl CH3

17. OH
Br

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PRACTICE MODULE CHAPTER 8 SK025

18.
HO

Br H
19.
C
CH3 CH2
CH2 OH
C OH

H
20.

HO

21.
CH3
C OH
CH3

22.
CH3 CH2CHCH2OH

23.
CH3
CH OH

24.
OH
CH3

25.
CH2 OH

164

PRACTICE MODULE CHAPTER 8 SK025
WORKSHEET 8.2 (a) PHYSICAL PROPERTIES

• Boiling point
• Solubility in water
BOILING POINT
Predict which of the compound in each of the following pairs is higher boiling point. Briefly explain
your answer.
a) CH3CH2OH and CH3CH2CH2OH
Answer :

b) CH3CH2CH2CH2OH and CH3CH2CH2CH2CH2CH2OH
Answer :

c) Ethanol and pentane
Answer :

d) 1-butanol and 1,3-prapanediol
Answer :

165

PRACTICE MODULE CHAPTER 8 SK025

e) Cyclohexanol and 1-hexanol
Answer :

2. Arrange the following compounds in order of increasing boiling point.
a) Ethanol, 2-butanol, 1-hexanol, 1-propanol
b) 1,2-ethanediol, butane, 1-propanol
c) 2-methyl-1-pentanol, 1-hexanol, 2,2-dimethyl-1-butanol
d) Butanal, 1-butanol, pentane, 1-chloropropane

Answer:

WORKSHEET 8.2 (b) PHYSICAL PROPERTIES
• Boiling point
• Solubility in water

SOLUBILITY
1. Predict which of the compound in each of the following pairs is more soluble in water.
Briefly explain your answer.

i) Butane and 1-propanol
Answer :

166

PRACTICE MODULE CHAPTER 8 SK025
ii) 1-pentanol and 1,4-butanediol
Answer:

iii) 1-butanol and 1-pentanol
Answer:

iv) 1-butanol and 2-methyl-2-propanol
Answer:

v) Cyclopentanol and 1-pentanol
Answer:

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PRACTICE MODULE CHAPTER 8 SK025
2. Arrange the following compounds in order of increasing solubility in water.
a) Ethanol, 2-butanol, 1-hexanol, 1-propanol
b) 1,2-ethanediol, butane, 1-propanol
c) 2-methyl-1-pentanol, 1-hexanol, 2,2-dimethyl-1-butanol
d) Butanal, 1-butanol, pentane, 1-chloropropane
Answer:

168

PRACTICE MODULE CHAPTER 8 SK025

WORKSHEET 8.3 PREPARATION

• Preparation alcohol by:
✓ Fermentation
✓ Hydration of alkenes
✓ Hydrolysis of haloalkanes
✓ Addition of Grignard reagent to carbonyl

• Outline synthesis of alcohol

Complete the following reaction.

Fermentation

C6H12O6 yeast +2 CH3 CH2 OH 2 CO2

Hydration of alkenes (electrophilic addition)

CH3 CH CH2 H2O CH3 CH CH3 Always follow Markovnikov’s
a) H2SO4 OH Rule to determining the major
product of Electrophilic
CH3 C CH2 H2O OH Addition.
b) CH3 H2SO4 CH3 C CH3
Rearrangement is required to
CH3 form more stable carbocation

OH OH

H2C CH CHCH3 H2O +CH3 CH CHCH3 CH3 CH2C CH3
c) CH3 H2SO4
CH3 CH3
minor major

OH

H2O
d) H2SO4

CH3 H2O OH
H2SO4 CH3

e)

Hydrolysis of haloalkanes (nucleophilic substitution)

CH3 CH CH3 NaOH (aq) CH3 CH CH3
a) Cl OH

167

PRACTICE MODULE CHAPTER 8 SK025

Cl NaOH (aq) OH
CH3 C CH3 CH3 C CH3
b) CH3
CH3

Cl NaOH (aq) OH
CH3 CH CHCH3 CH3 CH CHCH3
c) CH3
CH3

Br OH

NaOH (aq)
d)

Br NaOH (aq) OH
CH3 CH3

e)

Addition of Grignard reagent to carbonyl (nucleophilic addition)

CH3 CH CH2MgBr O OH
a) CH3 CH3 CH CH2 CH2
i. H C H
ii. H3O+ CH3
CH2OH
O
CH2OH
MgCl i. H C H
OH
b) ii. H3O+ CH3 CH CH2 CH CH3

O CH3

Mg Br i. H C H CH OH
CH3
c) ii. H3O+

CH3 CH CH2MgBr O
d) CH3 C

i. CH3 H
ii. H3O+

O

MgCl C

i. CH3 H

e) ii. H3O+

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PRACTICE MODULE CHAPTER 8 SK025

MgCl O CH3
f) C CH OH

CH3 CH CH2MgBr i. CH3 H OH
g) CH3 ii. H3O+
CH3 CH CH2 C CH3
MgCl O
C CH3 CH3
h) CH3
i. CH3 CH3
ii. H3O+ C OH

O CH3
C

i. CH3 CH3
ii. H3O+

O

C CH3
i. CH3 CH3 C OH
Mg Br CH3
ii. H3O+

i)

Outline synthesis of alcohol
a) Outline synthesis of 2-cyclopropyl-1-butanol from 2-cyclopropyl-1-butene

b) Outline synthesis of 2-methylcyclopentanol from 1-methylcyclopentene

c) Outline synthesis of 1-pentanol from 1-bromobutane

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PRACTICE MODULE CHAPTER 8 SK025

WORKSHEET 8.4 (a) CHEMICAL PROPERTIES

• Reaction alcohol with:
✓ Na
✓ Esterification
✓ Dehydration
✓ Substitution with HX, PX3, PCl5, SOCl2

Complete the chemical equation.

Reaction alcohol with Na (alcohol as an acid)

+CH3 CH2 CH2 Na +CH3 CH2OCH– 2Na+ 1/2 H2

a) OH

OH – +

+ Na O Na

b) + 1/2 H2

CH3 CH3
CH3 C OH
c) CH3 + Na CH3 C – + + 1/2 H2

O Na

CH3

Esterification (nucleophilic substitution-alcohol as nucleophile)

+CH3 CH2 CH2 O H+ O

CH3 C OH Δ CH3 C O CH2CH2 CH3 + H2O
+ H2O
a) OH + H2O

OH O H+ O
Δ CH3CH2 C O
+ CH3CH2 C OH

b)

CH3 + OH H+ CH3
CH3 C OH C Δ O C CH3
c) CH3 C CH3
O
O

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PRACTICE MODULE CHAPTER 8 SK025

Dehydration (elimination)

CH3 CH2 CH2 conc H2SO4 +CH3 CH CH2 H2O
a) OH Δ

OH conc H2SO4 + H2O
Δ

b)

CH3 CH3
CH3 C OH
c) CH3 conc H2SO4 +CH3 C CH2 H2O
Δ

Substitution with HX, PX3, PCl5, SOCl2 (nucleophilic substitution)

CH3 CH2 CH2 + HBr CH3 CH2 CH2 + H2O
a) OH Br

OH Br H3PO3

+ PBr3 +

b)

CH3 + PCl5 CH3 + POCl3 + HCl
CH3 C OH CH3 C Cl
c) CH3
CH3

CH2OH SOCl2 CH2Cl SO2 + HCl

+ +

d)

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PRACTICE MODULE CHAPTER 8 SK025

WORKSHEET 8.4 (b) CHEMICAL PROPERTIES

• Oxidation with:
✓ KMnO4/H+ (strong oxidizing agent)
✓ Cr2O72-/H+ (strong oxidizing agent)
✓ CrO3/H+ (strong oxidizing agent)
✓ PCC/CH2Cl2 (mild oxidizing agent)

Oxidation using acidified solution of permanganate, dichromate, chromate and Pyridinium
chlorochromate. (oxidation - the process of oxidizing; the addition of oxygen to a
compound with a loss of electrons)

Complete the following reaction.

CH3 CH2 CH2 PCC CH3 CH2 CH
a) OH CH2Cl2 O

CH2OH KMnO4/H+ O
Δ
C + 2+
OH
Mn

b)

OH O
PCC

c) CH2Cl2

CH3 CH2 CH CH3 Cr2O72-/H+ +CH3 CH2 C CH3 3+
d) OH Δ
O Cr

CH3 PCC no reaction
CH3 C OH CH2Cl2
e) CH3

CH3 CrO3/H+ no reaction
CH3 CH2 C OH Δ
f) CH3

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PRACTICE MODULE CHAPTER 8 SK025
WORKSHEET 8.4 (c) CHEMICAL PROPERTIES

• Chemical test:
✓ Lucas test (Reagent: conc HCl and anhydrous ZnCl2)- identification test
✓ Iodoform test (Reagent: excess I2 in NaOH)- detect methyl carbinol group

Suggest a chemical test to distinguish the following pairs
a) 1-pentanol and 2-butanol

Name of the test
Reagent
Equation

Observation

b) 2-propanol and 2-methyl-2-propanol
Name of the test
Reagent
Equation

Observation

c) 2-methyl-1-butanol and 2-metyl-2-butanol
Name of the test
Reagent
Equation

173

PRACTICE MODULE CHAPTER 8 SK025

Observation

d) 2-pentanol and 3-pentanol

Name of the test
Reagent

Equation

Observation

e) Ethanol and 1-butanol
Name of the test
Reagent
Equation

Observation

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PRACTICE MODULE CHAPTER 8 SK025

WORKSHEET 8.5 PHENOL

• Acidity: phenol vs alcohol vs water

• Reaction phenol with:
✓ Na
✓ NaOH

• Test using
✓ FeCl3
✓ Bromine water

1. Arrange the following compounds in ascending order of acidity
Phenol, ethanol, water. Explain.

Answer:

Reaction phenol with Na and NaOH (phenol as acid)

OH –+ 1/2 H2

+ Na O Na

+

OH –+ H2O

+ NaOH O Na

+

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PRACTICE MODULE CHAPTER 8 SK025

Identification test of phenol

a)
Name of the test

Reagent
Equation

Observation

b)
Name of the test

Reagent
Equation

Observation

WORKSHEET 8.6 (OBJECTIVE QUESTIONS)

1. What is the IUPAC name of the following 2. What is the IUPAC name of the following
compound?
compound? Br
CH3 CH3
CH3CHCHC(CH3)2
OH
OH
A. 1-bromo-2-methylcyclohexanol
A. 2-phenyl-1,4-dimethyl-3-pentanol B. 4-bromo-3-methylcyclohexanol
B. 4,4-dimethyl-2-phenyl-3-pentanol C. 2-bromo-1-methylcyclohexanol
C. 2,2-dimethyl-4-phenyl-3-pentanol D. 4-bromo-5-methylcyclohexanol
D. 1-tert-butyl-2-phenyl-1-propanol

176

PRACTICE MODULE CHAPTER 8 SK025

3. Which of the following are secondary 4. Arrange the following compounds in order of

alcohols? increasing boiling point.

I CH3CH2CH2OH
OH OH OH II (CH3)2CHOH

III HOCH2CH2CH2OH

I II III IV HOCH2CH2OH

A. I and II A. I < II < III < IV
B. I,II and III B. II < I < IV < III
C. I and III C. IV < III < II < I
D. II and III D. I < II < IV < III

5. Which of the following compounds has the 6. Which of the following alcohols would react

highest boiling point? fastest with Lucas reagent?

A. CH3CH2CH2CH2CH2OH A. (CH3)3CCH2OH
B. OH B. (CH3)2CHCH2CH2OH
C. (CH3)2C(OH)CH2CH3
CH3CHCH2CH3 D. CH3CH2CH2CH(OH)CH3
C. OH

CH3CCH3

OH
D. HOCH2CH2CH2OH

7. Which of the following compounds does not 8. What is the best choice of reagent for the
decolourise acidified potassium
permanganate? following conversion?

A. ?
CH3
CH3CH2OH CH3CHO
B. OH
A. KMnO4/H+
B. NaOH
C. PCC/CH2Cl2
D. Conc. H2SO4

C. (CH3)2CHOH
D. (CH3)3COH

177

PRACTICE MODULE CHAPTER 8 SK025

9. Which of the following alkenes is the major 10. Arrange the compound in increasing solubility
dehydration product of 2,2-dimethyl-1- in water.
butanol?
1,3-propanediol, 1,2-ethanediol, n-butane, 1-
A. CH3CH2C(CH3)=CHCH3 propanol
B. CH2=C(CH2CH3)2
C. (CH3)2CHC(CH3)=CH2 A. 1,3-propanediol <1,2-ethanediol < 1-propanol <
D. (CH3)2C=C(CH3)2 n-butane

B. 1,2-ethanediol < 1-propanol < 1,3-propanediol <
n-butane

C. n-butane < 1-propanol < 1,3-propanediol < 1,2-
ethanediol

D. n-butane < 1,3-propanediol < 1-propanol < 1,2-
ethanediol

11. Which of the following is the observation 12. Which of the following alcohol gives 2-
when aqueous iron (III) chloride is added to methylpropanoic acid when it is xidized?
phenol?
A. 1-butanol
A. Chlorobenzene is formed. B. 2-butanol
B. White fume are given off. C. 2-methyl-1-propanol
C. Iron (III) is reduced to iron (II). D. 2-methyl-2-propanol
D. A purple solution is formed.
13. Which of the following compounds is 14. When excess 2-butanol is heated with
concentrated sulphuric acid at 180° C, the
expected to have the highest boiling point? major product is

A. CH3CH2CH2OH A. CH3CH(CH3)OCH(CH3)CH2CH3
B. CH3CH(OH)CH3 B. CH3CH2CH=CH2
C. CH3OCH2CH3 C. (CH3)2C=CH2
D. CH3CH(OH)CH2OH D. CH3CH=CHCH3

15. When bromine is added to phenol, the 16. To produce the alcohol CH3CH2CH(OH)CH3,
brown color of bromine is decolourised and the reagents needed are
a white precipitate of 2,4,6-tribromophenol is
formed. This is an example of A. CH3COCH3 and CH3MgBr
B. HCHO and CH3CH2CH2MgBr
A. nucleophilic substitution C. HCHO and (CH3)2CHMgBr
B. free radical substitution D. CH3CHO and CH3CH2MgBr
C. electrophilic substitution
D. electrophilic addition

17. Alcohol F decolourises acidified potassium 18. Which of the following compound has the
manganate(VII) solution and forms a yellow greatest acidity?
precipitate with an alkaline solution of iodine.
Alcohol F is A. CH3OH
B. C6H5OH
A. CH3CH2CH(OH)CH2CH3 C. CH3CH2OH
B. (CH3)3COH D. C6H5CH2OH
C. CH3CH(OH)CH3
D. CH3CH2CH2OH

178

PRACTICE MODULE CHAPTER 8 SK025

19. Which of the following are expected to give a 20. Phenol and phenylmethanol differ in the

yellow precipitate with alkaline iodine reaction with

OH

I. bromine water

OH II. aqueous iron(III) chloride

III. sodium

I. II. III. CH3OH

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

179

WORKSHEET 8.7 (a) MAPPING PRACTICE MODULE CHAPTER 8 SK025
O OO

KMnO4/H+ CrO3/ H+ PCC Na O–Na+
Δ Δ CH2Cl2 O
O
H2O OH OCCH3
H2SO4 CH3 C OH ,H+
Δ Br
Br Br
NaOH(aq) conc H2SO4 Cl
Δ Cl
IUPAC name:
2-cyclopentanol HBr
Class of alcohol: 2o
PBr3
Conc HCl
ZnCl2 PCl5

SOCl2

Cl

Observation:
cloudy solution form within 5-10 minutes

180

PRACTICE MODULE CHAPTER 8 SK025

WORKSHEET 8.7 (b) MAPPING
O OO
C OH C OH C H

KMnO4/H+ CrO3/ H+ PCC Na CH2O–Na+
Δ Δ CH2Cl2 O
O
CH2 CH2O C CH3
CH3 C OH ,H+
HBr CH2 OH Δ CH2
peroxide
conc H2SO4 CH2 Br
CH2 Br Δ
NaOH(aq) CH2 Br
HBr
IUPAC name: CH2 Cl
cyclopentylmethanol PBr3
Class of alcohol: 1o CH2 Cl
PCl5

SOCl2

i. HCHO
ii. H3O+

MgBr

181

WORKSHEET 8.7 (c) MAPPING PRACTICE MODULE CHAPTER 8 SK025

–+

O Na

–+ Na Br
OH
O Na OH
NaOH (aq) Br2 (aq)

FeCl3 (aq) Br Br
OH
FeCl3 Observation:
white precipitated formed

Observation:
purple complex formed

182

PRACTICE MODULE CHAPTER 8 SK025
WORKSHEET 8.8 Clone MODEL PSPM
Q1: clone PSPM 2019/2020
Compound M and N are isomers with molecular formula C4H8O containing a single ring. The
reaction of M and N with sodium metal forms gas bubbles. When M is heated with acidified
solution of sodium dichromate, orange solution turns green and compound P, C4H6O2 is formed.
N does not decolorise acidified solution.
a) Draw the structure of M, N and P.
b) Write all chemical equations involved.
c) Write the structural formula of product formed when P reacts with N. State the catalyst used.
Q2: clone PSPM 2020/2021
Compounds K and L are isomers of linear carbon chain alcohol with molecular formula of
C4H10O. Oxidation of K produces a carboxylic acid, whereas L produce carbonyl compound.
a) Deduce the structural formulae of K and L.
b) Draw the product of oxidation of K and L.
c) State the oxidizing agent used for both reaction.

Prepared by : Miss Zanarina Binti Sapiai
Checked by : Mdm Suhaibah & Mdm Siti Fatimah

183

PRACTICE MODULE CHAPTER 9 SK025

CHAPTER 9 : CARBONYL
9.2 NOMENCLATURE OF CARBONYL COMPOUNDS

WORKSHEET 9.1 Br NO2
5.
Write the correct IUPAC name.
OC
1. H3C CH2 CH2 CH2 CH
O H

2.

Br H3C 6.

H3C C CH2 CH C H CH3 O

H2C CH3 O H3C CH CH2 C H

3. H O 7. CH3 O CH3
CH C C Cl
H3C CH2 CH2

CH3

4. H O 8. CH2
CH3 O

H3CH2C CH C

9. O
Cl

CH2CH3

184

PRACTICE MODULE CHAPTER 9 SK025

10.

O
CH3CHCHCH2CH3

CH3

WORKSHEET 9.2

Draw the structure for the following IUPAC name.

1. propanal 2. 2-methylpropanal

3. Phenylmethanal @ benzaldehyde 4. 4-nitrobenzaldehyde

5. 2-pentanone 6. 4-methyl-2-pentanone

7. 1-phenyl-2-propanone 8. 1-cyclopentyl-2-butanone

191

9. acetophenone PRACTICE MODULE CHAPTER 9 SK025
10. 1-chloro-2-pentanone

9.3 PREPARATION OF CARBONYL COMPOUNDS
WORKSHEET 9.3
Preparation of carbonyl compound.
Complete the following reaction.
i) Ozonolysis of alkene

ii) Friedal-Craft Acylation

iii) Oxidation of alcohol CH3 O H
1o alcohol CH3CH2C C
CH3
H
a) CH3CH2CHCH2OH PCC/CH2Cl2
) O
b) CH2OH PCC/CH2Cl2
) CH

191

PRACTICE MODULE CHAPTER 9 SK025

c) CH3 CH3 O H
) CH3CHCH2CH2OH PCC/CH2Cl2 CH3CHCH2C

2o alcohol

OH O
a) CH3CCH3 KMnO4/H+ CH3 C CH3

)H O
)b) OH KMnO4/H+

)

)
9.4 CHEMICAL PROPERTIES OF CARBONYL COMPOUNDS
WORKSHEET 9.4
Complete the following reaction.

i) Addition with KCN, H3O+ or NaCN, H3O+

O
KCN/H+

a) CH3CH2 C CH3
)

)

b) NaCN/H+
CH3CH2CHO

)

)c) O NaCN/H+
b) CH3CCH3

)

)d) CH3 O KCN/H+

)b) CH3CHCH2C H

)

192

PRACTICE MODULE CHAPTER 9 SK025

ii) Reduction to alcohol

a) CH3CH2CHO i) LiAlH4
ii) H3O+
b)

) O NaBH4 in methanol
b)

) CH3CH2CH2CH

) O
c)
) CH3CH2CCH3 NaBH4 in methanol

)

d) O H2/Pt
)

CH2CCH3

)

)
iii) Condensation with ammonia derivatives

a)

iv) Oxidation with KMnO4/H+ and Cr2O72-/H+

O + F
a) CH3 CH2 CH2 C H
K2Cr2O7, H

b)

193

PRACTICE MODULE CHAPTER 9 SK025
WORKSHEET 9.5

1. Based on the reaction scheme below, state the reagent A and draw the structure of M
and N.

WORKSHEET 9.6
Chemical Test

i) Suggest a chemical test to distinguish the following pairs
a) 1- propanol and propanal

Name of test :
Reagent :
Equation :

Observation :

194

PRACTICE MODULE CHAPTER 9 SK025

b) Methanal and ethanal
Name of test :
Reagent :
Equation :

Observation :

c) Propanal and propanone
Name of test :
Reagent :
Equation :

Observation :
195

PRACTICE MODULE CHAPTER 9 SK025

WORKSHEET 9.7 2. What is the IUPAC name of the following
compound?
MULTIPLE CHOICE QUESTIONS
O
1. What is the IUPAC name of the following
compound? CH3 CH3

O

CH

NO2 A. 2-pentanone
B. 3- pentanone
A. 4-nitrobenzaldehyde C. 5-hexanone
B. 2,4-dinitrobenzaldehyde D. 2-hexanone
C. 1-nitroheptanal
D. Benzophenone 4. Which of the following groups can be
3. Which of the following alcohols can be classified as carbonyl?
oxidized to a ketone?
A. Carboxylic acids
A. CH3CH2OH B. Aldehyde and ketone
B. CH3CH(OH)CH3 C. Ester
C. CH3CH2CH2OH D. Ether
D. CH3OH
6. Which of the following pair of compounds can
5. When reacted with a reducing agent, be distinguished by using Tollens” reagent?
aldehyde turn to
A. CH3COOH and HCOOCH3
A. ketones B. HCOOH and HCHO
B. carboxylic acids C. CH3COCH3 and CH3CH2CH2OH
C. secondary alcohols D. CH3CHO and CH3CH3NH2
D. primary alcohols
8. Which of the following compounds would rea
7. An organic compound T, forms a yellow with alkaline iodine solution and with 2,4-
precipitate with alkaline iodine solution, but dinitrophenylhydrazine?
does not react with [Ag(NH3)2]+ solution.
Compound T may be, A. C6H5CHO
A. CH3CHO B. C6H5COCH3
B. CH3CH2CH2COCH3 C. CH3CH(OH)CH3
C. CH3CH2COCH2CH3 D. CH3CH2COCH2CH3
D. CH3CH2CHO
10. Which of the following would attack the carb
9. The intermediate which is formed during the atom in the carbonyl group?
reaction between propanone and hydrogen
cyanide is known as A. Nucleophile
B. Electrophile
A. A free radical C. Free radical
B. A carbonium ion D. Carbonium ion
C. A nucleophile
D. A carbanion

196