MOCK ANSWER SCHEME FOR STPM 2022

962 / 3 : CHEMISTRY PAPER 3

16. a) SN1 [1] b) 2-bromo-2-methylpropane [1] b) Each structure X, Y, Z [1] x 3 ; Equation [1] x 2 [5]
Type of reaction [1]

c) [1]
d) i. prevent the formation of alkanes or alkenes or alkynes [1]
ii. First step : CH3CHO Second step : H3O+ [2]
iii. cooling agents and lubricants / additive in paints, plastics
and rubber as a plasticiser / flame retardant (fire extinguisher)

17. a) CH3CH2CH2COOCH3 [1]

b) i. P : CH3CH2CH2COOH Q : CH3OH [1]
ii. P : CH3CH2CH2COCl [1] 20. a) m1-m3 : structure of A, B, C [3]
c) i. ethanamine / ethylamine [1]
ii) CH3CH2CH2COCl + CH3CH2NH2 → (heat)
CH3CH2CH2CONHCH2CH3 + CH3CH2NH3Cl [1]
d) P is more soluble in water while methyl butanoate is
sparingly soluble in water [1]
b) m4 : elimination : excess conc. H2SO4 ; reflux [1]
- since P can form hydrogen bond with water ester cannot [1]
m5 : ozonolysis : 1) O3 in CH2Cl2 , cold [1]
m6 : 2) DMS [1]
18 a) m1 – m5 : Each structure [1] x 5 [5]
c) m7-m9 : Each arrow [1] x 2 intermediate [1] [3]

b) m6 : equation m7 : major product m8 : minor product [1]

CH3CH2CH=CH2 + HCl → d) m10 – m12 : two reagent [1] x 2 Equation [1] [3]
U CH3CH2CHClCH3 + V : CH3CH2CH2CH2Cl
(major) (minor)
* wide range of answer will probably be accepted
m9 : U is major since it follows Markovnikoff’s rule [1]
e)m13 : Test : Fehling’s solution / Tollens’ reagent / Iodoform
m10 : in the addition of H-Cl to unsaturated C=C, H is
m14 : propanal gives brick-red precipitate (FS) / silver mirror
preferred to add to C with more H [1]
(TR) while propanone shows no observable changes or
c) m11 : 3o carbon radical is more stable [1]
propanone give yellow precipitate (Iodoform) while propanal
m12 – m15 : each steps [1] x 4 [4]
shows no observable changes [1]
m15 : equation : [1]

19. a) Each step and reagent/condition [1] x 9 [9]

 Section A

CH3CH(OH)CH2CH=CHCH3 is sparingly soluble in water since it has 7 C. It has 2 functioning group. It exhibit
1. D
both geometrical and optical isomerism, and has 2 sp2 and 4 sp3 C hybrid orbital and 1 sp3 O hybrid orbital
Noradrenaline has C* atom hence optical active. It has 4 functioning group (phenol, 20 alcohol, 10 amine,
2. A
benzene). It can dehydrate as it has 2o alcohol and can undergoes coupling reaction with benzenediazonium ion
3. C Cl• (electrophile) ; NO2+ (electrophile) ; AlH4- (nucleoophile) ; H+ (electrophile)
Phenol has lower melting point than benzoic acid (form dimer) ; chloroethane has lower melting point than
4. D bromoethane (higher RMM) ; n-butane has higher melting point than methylpropane (branch) ; methyl ethyl ether
has lower melting point than propan-1-ol (hydrogen bond)
Toluene can undergoes free radical substitution (-CH3) and addition (benzene) and electrophilic aromatic
5. C
substitution reaction (ortho para subst)

6. D

7. B Chlorobenzene does not undergoes hydrolysis under atmospheric pressure

8. B Since vitamin B1 has 10 alcohol, it react faster with Na
X form cyanohydrin of CH3CH2CH(OH)CN. Therefore it can undergoes dehydration to form CH3CH=CHCN ; it
9. A hydrolysed to form CH3CH2CH(OH)COOH ; it’s a nucleophilic addition ; X cannot be formed from haloalkane
and hydrogen cyanide/
Ethanoyl chloride is liquid ; It react with phenol in alkaline condition to form ester and primary amine to form 20
10. C
amide ; It does not form dimer
C6H5COCl + CH3CH2CH2OH → (one way) C6H5COOCH2CH2CH3 (sweet smell) + HCl (white fume) ; does not
11. A
required catalyst.
Alanine can form only one dipeptide Ala-ala ; it is optical active and can react with R-COCl to form HCl ; it is
12. A
neutral as it form zwitterion.
Due to aniline, it form salt when react with acid (neutralization) and react to form benzenediazonium chloride
13. A/B
when react with NaNO2/HCl 0-5oC.

14. C Nylon 6,6 is polyamide, PVC is addition polymer ; terylene is polyester ; rubber is addition polymer

15. D Monomer is CH2=CHCOOH and react via addition polymerization.