TUTORIAL CHEMISTRY SK025

9.0 : CARBONYL COMPOUNDS SK O25

11. Compounds W and X have the molecular formula of C8H8O. W reacts with hot Fehling’s
solution producing a red precipitate. X gives negative result towards Fehling’s test but it
reacts with LiAlH4 followed by hydrolysis to form alcohol Y. Both X and Y reacts with iodine
in NaOH solution to yield a yellow precipitate.

Determine the structural formulae of W, X and Y.

Give the products of the reactions between W and LiAlH4/H+, and acidified potassium
dichromate solution respectively.

TUTORIAL 9.0 CARBONYL COMPOUNDS

Unit Kimia, KMKt 2020/2021 8

10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

SECTION A

1 Boiling points of carboxylic acids is higher than those of corresponding
alcohols is due to

A Strong London dispersion forces
B Strong dipole-dipole interaction
C Strong hydrogen bonded dimer
D Strong covalent bond

2 Which interaction has the greatest effect on the physical properties of
carboxylic acids?

A Covalent bond
B Hydrogen bond
C van der Waals force
D Dipole-dipole force

3 Which is the correct order of boiling points of carboxylic acids, from the
lowest to the highest?

A methanoic acid, ethanoic acid, butanoic acid, propanoic acid
B methanoic acid, propanoic acid, butanoic acid, ethanoic acid
C methanoic acid, ethanoic acid, propanoic acid, butanoic acid
D ethanoic acid, methanoic acid, propanoic acid, butanoic acid

4 What factor can decrease the solubility of carboxylic acid in water?

A The increase in length of the hydrocarbon chain.
B The decrease in length of the hydrocarbon chain.
C The increase in number of carboxyl group.
D The number of hydrogen bond.

5 Which of the following acids is the most soluble in water?
A Benzoic acid
B Butanoic acid
C Heptanoic acid
D 1,4-benzenedicarboxylic acid

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10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

6 Which of the following is the correct order of decreasing acidity?
A FCH2COOH > CH3COOH > F2CHCOOH
B F2CHCOOH > Cl2CHCOOH > CH3COOH
C CH3COOH > ClCH2COOH > FCH2COOH
D CH3COOH > ClCH2COOH > BrCH2COOH

7 Arrange the following in the decreasing order of their acidity.

PQR

A P>Q>R
B R>Q>P
C P>R>Q
D Q>P>R

8 Which of the following would react with benzoic acid to produce benzoyl
chloride?
A Cl2
B HCl
C NaCl
D SOCl2

9 Which of the following is the best reagent(s) for the following
conversion?

COOH CH2OH

A H2, Pt
B KMnO4, H+, 
C LiAlH4 followed by acidification
D CH3OH, H+, 

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10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

10 Which of the following is the most suitable method for preparing benzoic
acid from ethyl benzene?

A Boiling with concentrated HNO3

B Boiling with alkaline KMnO4 followed by acidification

C Addition of Cl2 in the presence of sunlight followed by NaOH in
CH3CH2OH

D Addition of Cl2 in the presence of sunlight followed by boiling with
aqueous NaOH

11 What alcohol is used in the manufacturing of the following ester?

OH CH3

Br CH2CHCOOCHCH3

A methanol

B 2-propanol

C 2-bromoethanol

D 3-bromo-1,2-propanediol

ABC D

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

12 Which of the following would produce an acid?
I. Hydrolysis of a nitrile.
II. Oxidation of primary alcohol.
III. Reaction of a Grignard reagent with a ketone followed by hydrolysis.

13 Which of the following acid would decolourise acidified KMnO4 solution
under a suitable condition?
I. Methanoic acid

II. Benzenedicarboxylic acid
III. Cyclohexanecarboxylic acid

14 Which of the following is/are correct regarding to the compound below?

CH2OH
HO C COOH

OH

I. It exists as a pair of enantiomers.
II. 1 mole of the compound would react with 3 moles of PCl5
III. 1 mole of the compound would react with 2 moles of sodium hydroxide

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10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

15 Which of the following would produce an acid chloride when treated with

SOCl2?

I. CH3CH2OH

II. O O

HO C C OH

III. COOH
HOOC

SECTION B

1. (a) Arrange the following compounds in order of increasing boiling point.
Explain your answer.
pentanal, butanoic acid, pentane, 1-butanol

(b) Arrange the following compounds in ascending order of solubility in water.
Explain your answer.
i. Propanol, propanoic acid, propane, propanal
ii. octanoic acid, benzoic acid, ethanoic acid, butanoic acid

(c) Arrange the following compounds in order of decreasing acidity.
i. phenol, 1,3-propanediol, propanedioic acid, propanoic acid.
ii. acetic acid, ethanol, trifluoroacetic acid, 2,2-difluoroethanol.

(d) Refers to the TABLE 1 below. Which acid is the strongest acid?

Explain your answer

Acid ethanoic acid 2-chloroethanoic acid 2,2-dichloroethanoic
acid

Formula CH3COOH ClCH2COOH Cl2CHCOOH
Ka 1.80 x 10-5 1.58 x 10-3 5.01 x 10-2

TABLE 1

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10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

2. (a) Complete the reaction

A

Na SOCl2 B
CH3CH(OH)CH3, conc H2SO4 pyridine

D CH3CH2CH2CH2COOH


NaOH

C

3. Identify compounds E-J in the following reactions.

i. Cl i. KMnO4, OH-, 

CH3CH CH2CHO ii. H3O+ E

ii. CH3CH2CH2CH2OH i. KMnO4, OH-,  F
ii. H3O+

iii. G + NaOH -+

CH3CH2COO Na + H2O

iv. CH2CH2OH CH3CH2COOCH2CH2
+H
conc. H2SO4


v. CH2COOH I CH2COCl
+ HCl + SO2
vi. i.LiAlH4
CH3CH2COOH ii.H3O+ J

Unit Kimia, KMKt 2020/2021 59

10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

4. Draw the structural formula of the product formed in each reaction.

i. (CH3)2CHCOOH + CH3CH2CH2CHOH conc. H2SO4


CH3

ii. OH SOCl2

COOH pyridine

iii. CH2CH2CN
H2O/H+

5. The below reaction scheme shows the steps involved in the synthesis of
butanoic acid from propanoic acid.

CH3CH2COOH I SOCl2 NaCN, alcohol L
pyridine K reflux
CH3CH2CH2OH

II H3O+

III CH3CH2CH2COOH

CH3CH2CH2MgCl

(a) Suggest the reactant and conditions that can be used in step I, II and III.
(b) Identify the compounds K and L.

6. Outline the synthesis of the following:

(a) 1-bromopropane to butanoic acid

(b) 2-propanol to butanoic acid

(c) CH3 COOCH2CH3

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10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

7. When M is hydrolysed by water, the products formed are an organic acid N,
with molecular formula C4H8O2 and an alcohol P , C4H10O. P give positive result
with iodoform test.

i) Identify M, N and P
ii) Write the chemical equation for the above reactions.

8. Compound Q and R are isomers with molecular formula C9H12O. Q is optically
active while R is optically inactive. On treatment with KMnO4/H+, heat, Q gives
benzoic acid but R cannot be oxidized. Draw the structure Q and R.

9. Complete the reaction.

U

CH3CH2OH, conc H + 

CH2CH2COOCH3 CH2CH2COOH CH2CH2CN
IV V CH2CH2COOOCCH3

NH 3

excess SOCl2 VI
pyridine
S

T

10. Methanoic acid acts as a reducing agent and gives positive result with Tollen’s
test but ethanoic acid does not. Explain this statement.

Unit Kimia, KMKt 2020/2021 61

10.0: CARBOXYLIC ACIDS & ITS DERIVATIVES SK O25

Unit Kimia, KMKt 2020/2021 62

11.0: AMINES SK O25

SECTION A

1. Which of the following gives the correct trend in the boiling points of the isomeric amines?
A. (CH3)3N < CH3CH2NHCH3 < CH3CH2CH2NH2
B. CH3CH2CH2NH2< CH3CH2NHCH3< (CH3)3N
C. CH3CH2CH2NH2< (CH3)3N < CH3CH2NHCH3
D. (CH3)3N < CH3CH2CH2NH2< CH3CH2NHCH3

2. The structural formulae of a few amines are shown below.

P: CH3NHCH3 R: CH3CH2CH2NH2

Q: C6H5NHCH3 S: C6H5NH2

The correct order of increasing strength of basicity for P Q, R and S is …

A. Q<R<P<S

B. Q<S<R<P

C. S<Q<R<P

D. S<P<R<Q

3. Which of the following could be reduced to form 1-propanamine?
A. CH3CH2NO2
B. CH3CH2CONH2
C. CH3CH2CH2CN
D. CH3CHCON(CH3)2

4. Which of the following compound is used to prepare a solution of diazonium salt which is
stable below 5°C?

A. C.
NH2 CONH2

B. D. CH3
CH2 NH2

NH2

11.0: AMINES SK O25

5. When aqueous bromine is added to phenylamine, the brown colour of bromine is
decolourised. Which of the following statement explains this observation?
A. The NH2 group is oxidized to NO2.
B. Bromine reacts with phenylamine to form a colourless complex.
C. One of the hydrogen atoms in the NH2 group is replaced by bromine atom.
D. One of the hydrogen atoms in the benzene ring is replaced by bromine atom.

6. Compound Z has the following properties:
• Dissolves in dilute hydrochloric acid
• Forms an orange precipitate when a solution of phenol in aqueous NaOH is added to
a cold solution of Z in dilute HCl and NaNO2
Which of the following compounds is Z?
A.
NH2

B.

NH2

C.
CONH2

D.
CH2 NH2

7. When benzenesulphonyl chloride is added to compound X, a precipitate is formed which
dissolves in excess KOH. The precipitate reappears when a mineral acid is added. X is
A. (CH3CH2)3N
B. CH3CH2NH2
C. CH3CH2CONH2
D. CH3CH2NHCH3

8. An amine is considered a strong base when the …
A. pKa value of its conjugate base is small.
B. pKa value of its conjugate acid is small.
C. pKa value of its conjugate base is large
D. pKa value of its conjugate acid is large.

11.0: AMINES SK O25

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

9. Which of the following compounds react with benzenesulphonyl chloride?
I. Benzene-1,4-diamine
II. N-Methyl-2-pentanamine
III. N-Ethyl-N-methylcyclohexanamine

10. Which of the following statement(s) about phenylamine is/are true?

I. It is a weaker base than ammonia.
II. It gives a white precipitate with aqueous bromine.
III. It liberates nitrogen gas when heated with a mixture of sodium nitrite and dilute

hydrochloric acid.

11. + -

X SnCl2, H Br2, OH
NH2 Y

Choose the correct statement(s) based on the reaction scheme above.
I. Y is an amide.
II. X is a nitro compound.
III. X is a nitrile compound.

12. Compound X gives a white precipitate with Hinsberg’s reagents. X could be
I. (CH3)3N
II. C3H7NH2
III. CH3NHC2H5

13. Which of the following statement(s) is/are true?
I. Ammonia is stronger base than ethylamine.
II. Phenylamine is insoluble in water but soluble in dilute sulphuric acid.
III. Aniline reacts with warm nitrous acid to liberate nitrogen gas.

14. Which of the following pairs of compounds produce primary amines when under suitable
conditions?

I. C6H5CN and LiAlH4 followed by H+

II. CH3CH2CONH2 and NaBH4 followed by H+

11.0: AMINES SK O25

III. CH3CONHCH3 and NaOH(aq)/Br2

15. When aqueous bromine is added to phenylamine, 2,4,6-tribromophenylamine isformed as
shown below.

NH2 NH2

Br Br

+ 3Br2(aq) + 3HBr

Br

Which of the following statement(s) is/are true?
I. 2,4,6-Tribromophenylamine is formed as a white precipitate.
II. The reaction can be described as an electrophilic substitution reaction.
III. The delocalization of the lone pair of electrons on the N atom into the benzene ring

activates the phenylamine molecule.

SECTION B

1. Classify the following amines as 1, 2 or 3 and give their IUPAC names:

i. CH3CH2CH2NH2

ii. CH(CH3)2
CH3 CHNH
CH3

iii. C6H5CH(CH3)CH2NH2

iv. NH2

Cl

v. C6H5 N CH2 CH3
CH2 CH2 CH3

11.0: AMINES SK O25

2. Draw the structural formulae for the following compounds:
(a) 2-propanamine
(b) 3-aminobenzoic acid
(c) N-butyl-N-ethylaniline
(d) N,N-dimethyl-1-butanamine
(e) trimethylamine

3. (a) Explain why the boiling point of N,N-dimethylmethanamine is 4C while 1-
propanamine is 49 C.

(b) Compare the solubility of trimethylamine and methylamine in water.
Explain your answer.

(c) Arrange the following compounds in ascending order of basicity.
Explain your answer.
ammonia , methanamine, aniline, p-nitroaniline

4. Arrange the following compounds in ascending order of boiling point and explain your
answer.

1-propanol, ethanoic acid, chloroethane, 1-propanamine

5. Identify A to E in the following reactions.

(a) CH3CH2Cl + A ⎯→ (CH3CH2)2NH + HCl

(b) (CH3)3CCH2CN i) LiAlH4

B

ii) H3O+

(c) (CH3)2CHCONH2 ⎯⎯C → CH3CH(CH3)CH2NH2

(d) NH2
Sn, HCl
NH2
D E

(e) CH3 CH2 C O CH3 CH2NH2 + 2NaBr + Na2CO3 + 2H2O
NH2

11.0: AMINES SK O25

6. Based on the reaction below, draw the structure of J, K, L M, and N.

0-5C

7. Write the reaction equation for the reaction between nitrous acid, HNO2, and:
(a) ethanamine
(b) N- Methylmethanamine
(c) N,N-dimethylethanamine
(d) aniline

8. Show how each of following compounds can be synthesized:
a) 2-methyl-1-propanamine from 2-propanol

b) OH from benzene
CN
CH3

9. Suggest a chemical test to distinguish:
a) aniline from benzamide
b) ethanamine fromN,N-diethylethanamine

11.0: AMINES SK O25

10. When a compound with a molecular formula of C7H9N was treated with Hinsberg’s reagent
and nitrous acid, HNO2 respectively, the following results were obtained:

Test Observation

Hinsberg’s test: Clear solution formed.
Addition of KOH Precipitate formed.
Addition of HCl

Nitrous acid test No N2 gas is released below 5C

Based on the above observations, draw one possible structural formula of C7H9N and write
all the equations involved.

11. Arrange P, Q, R, and S in order of increasing basicity and explain your answer.

H H
N CH3 CH2 CH2 N

H H

P Q

CH3 CH3
CH3 CH2 N CH3 CH2 N

H CH3

R S

CHAPTER 12.0 : AMINO ACIDS SK O25

SECTION A

1. The general structural formula of an amino acid is
A. H
RCH
NH2
B. H
R C OH
NH2
C. O
R C NH2
D. H
R C COOH
NH2

2. Amino acid is a compound which has at least one
A. Amino group and one amide group.
B. Amino group and one hydroxyl group.
C. Amino group and one carboxyl group.
D. Hydroxyl group and one carbonyl group.

3. Zwitterion are
A. Basic
B. Acidic
C. Neutral
D. Carry only negative (-) charge

4. Which of the following statement is true about 2-aminoethanoic acid?
A. It exhibits optical isomerism.
B. It exists in the anionic form in acidic solution.
C. It forms zwitterions in aqueous solution
D. It is soluble in non-polar solvents.

5. What species is produced when 2-aminopropanoic acid (pI = 6) is dissolved in
a solution with pH = 2?

Unit Kimia KMKt (2020/2021)

CHAPTER 12.0 : AMINO ACIDS SK O25

A. H

-

H3C C COO
+NH3

B. H
H3C C COOH
+NH3

C. H

-

H3C C COO
NH2

D. H
H3C C COOH
NH2

6. A protein is
A. a polysaccharide.
B. a polymer of amino acids.
C. a saturated ester of glycerol.
D. one of the units composing a nucleic acid.

7. Type of bond between nitrogen and carbonyl group is
A. Hydrogen bond
B. Covalent bond
C. Peptide bond
D. Disulphide bond

8. Identify the peptide bond for the following polypeptide.
A B CD

OOO

NH CHC NH CHC NH CHC

CH2SH CH3 CH(CH3)2

Unit Kimia KMKt (2020/2021)

CHAPTER 12.0 : AMINO ACIDS SK O25

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

9. Consider the following amino acid:

H

NH2CH2 CH2 CH2 CH2 C COOH pI = 9.74

NH2

Which of the following statement(s) is(are) true about the amino acid?

I. It is in anionic form in neutral solution.

II. It is in cationic form in acidic solution.

III. It exists in zwitterionic form in solution with pH 9.74

10. COOH
H2N

Bacteria requires p-aminobenzoic acid (PABA) in order to biosynthesise folic
acid, an essential growth factor. PABA

I. exists as a pair of optical isomers

II. reacts with aqueous NaOH to form a salt

III. reacts with hydrochloric acid to form a salt

SECTION B

1. (a) Define -amino acid.
(b) Name the following -amino acids using the IUPAC nomenclature:
NH2 CH COOH
i.
CH(CH3)2
NH2 CH COOH
ii.
CH2C6H5
NH2 CH COOH
iii.
CH2OH
NH2 CH CH2 CH2 COOH
iv.
COOH

Unit Kimia KMKt (2020/2021)

CHAPTER 12.0 : AMINO ACIDS SK O25

2. Draw the structural formulae of the following compounds:
(a) 2-amino-4-methylpentanoic
(b) 2-amino-3-hydroxybutanoic
(c) 2-amino-3-methylpentanoic acid

3. (a) What is a zwitterion?
(b) Draw the structure of zwitterion for glycine, 2-aminoethanoic acid.

4. (a) What is meant by an isoelectric point?
(b) The isoelectric point of valine, 2-amino-3-methylbutanoic acid is 6.
Predict the structural formula of valine at
i. isoelectric point
ii. pH 12
iii. pH 1

5. The structural formula of tyrosine is
COOH

HO CH2 CH
NH2

Predict the structural formula of the product formed when tyrosine reacts with
(a) NaOH(aq)
(b) HCl
(c) CH3OH in the presence of concentrated H2SO4, reflux
(d) NaNO2,HCl

6. (a) What is a peptide bond?

(b) Write the reaction between phenylalanine and glycine to produce a
dipeptide phe-gly.

H

H H2N C COOH
H2N C COOH CH2

H

Unit Kimia KMKt (2020/2021)

CHAPTER 12.0 : AMINO ACIDS SK O25

Glycine Phenylalanine

7. (a) All amino acids are optically active except glycine, 2-aminoethanoic
acid. Explain this statement by using serine, 2-amino-3-
hydroxypropanoic acid.

(b) Draw all possible stereoisomers of serine.

8. 2-aminoethanoic acid and 2-aminopropanoic acid are amino acids. Draw all
possible dipeptides arising from these amino acids. Indicate the peptides
bond.

9. Two molecules of glutamic acid react to form a dipeptide .Draw the structure
of the dipeptide . Based on the structure below, is glutamic acid acidic or
basic ? Explain by drawing the structure of zwitterion .

10. The structure of aspartic acid is as follows:

O NH2
OH

C C H2C HC

HO O

Give its IUPAC name. Draw the structure of the products when aspartic acid
is reacted with methanol in the presence of concentrated H2SO4, and when
aspartic acid reacts with another molecule of aspartic acid. What is the net
charge of aspartic acid in a basic medium?

Unit Kimia KMKt (2020/2021)

13.0: POLYMERS SK O25

SECTION A

1. Copolymer is best described as
A. an addition polymer
B. a naturally occurring polymer
C. polymer that softens upon heating and can be remould
D. a polymer consisting of more than one type of monomer

2. Which of the following is NOT a naturally occurring polymer?
A. Starch
B. Protein
C. Terylene
D. Cellulose

3. Which of the following is a monomer for synthetic rubber?
A. Ethene
B. Propene
C. 2-Methyl-1,3-butadiene
D. Methyl-2-methylpropenoate

4. Which of the following compounds can undergo self-condensation to form a polymer?
A. CH3CH=CH2
B. HOCH2CH2OH
C. H2NCH2CH2CH2NH2
D. HOCH2CH2CH2CH2COOH

5. Polymer T has a structural formula as shown below.

Choose the correct pair of monomers to make the above polymer.
A. CH2=CHCl and CH2=C(CH3)CH=CH2

13.0: POLYMERS SK O25

B. ClHC=CHCl and CH2=C(CH3)CH=CH2
C. CH2=CClCH=CH2 and CH2=CHCH3
D. CH2=CHCl and CH3C(CH3)=CHCH3

6. Which of the following compounds can react with ethane-1,2-diol in a condensation
polymerisation reaction ?
A. C6H5COOH
B. CH3CH=CH2
C. HOC6H4COOH
D. ClOCC6H4COCl

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

7. When nylon-6,6 is produced from a dicarboxylic acid and a diamine,
I. ammonia gas is liberated
II. peptide linkages are formed
III. condensation polymerisation occurs

8. Ethene and polyethene have similar
I. empirical formula
II. melting point
III. relative molecular mass

9.

The formation of polymer P in the above reaction is considered as
I. hydrolysis
II. esterification
III. condensation

13.0: POLYMERS SK O25

10. What are the effects of cross-linking in a polymer?
I. The solubility decreases.
II. The softening point increases.
III. The polymer becomes harder.

SECTION B
1. Give the structural formula of the monomer for the following polymers.

(a)
(b)

(c)
(d)

(e)

2. Predict the structure of polymers that are formed by copolymerization of
(a) CH2=CHCN and CH3CH=CHCl

13.0: POLYMERS SK O25

(b) HOOCC6H4COOH and HOCH2(CH2)3CH2OH

3. The structural formulae of three organic compounds are given below
Structure I
CH2=CHCl
Structure II

Structure III
HOCH2CH2OH
Choose an appropriate monomer that can undergo addition polymerization and condensation
polymerization.
4. Draw the structural formula of the monomer(s) for the polymers given below:
(a)

(b)

(c)

5. (a) Define condensation polymerization.
(b) When compound P, C8H10 is refluxed with acidified potassium permanganate solution,
the product is Q, C8H6O4. When Q reacts with methanol in the presence of an acid

13.0: POLYMERS SK O25

catalyst, compound R C10H10O4 is formed, which is a monomer of Dacron. Predict the
structure of P, Q and R.

6. (a) Draw the structural formula of
i. hexanedioic acid
ii. 1,6-hexanediamine

(b) Write an equation for the reaction between both compounds to form a polymer.

(c) Name the functional group of the polymer formed in (b).

(d) Write the repeating unit of this polymer.

(e) Give the general name of this polymer.

(f) Name the type of polymerization.

TThyhyoaoauunn!!kk