MOCK ANSWER SCHEME FOR STPM 2018

962 / 3 : CHEMISTRY PAPER 3

16. a) - X : CH3CH2Cl in AlCl3 [1] 19. - Structure of 2-methylpropene [1] Equation [1] P [1]
- Y : KMnO4 / H+ under reflux [1]
- Z : conc. HNO3 in conc. H2SO4 under reflux [1]
b) i. - CH3CH2CONH2 [1]
ii. - CH3CH2COOH + PCl5  CH3CH2COCl + H2O [1] - Type of reaction : electrophilic addition reaction [1]
- CH3CH2COCl + NH3  CH3CH2CONH2 + HCl [1] - P is the only product according to Markovnikoff’s rule [1]
iii. - propanoyl chloride [1] - Equation [1] Q [1]
17. a) i. - CH3CH2CH(CH3)NH2 [1]
ii. - CH3CH2CH(CH3)NH2 [1]
iii. - react with HCl [1] - Type of reaction : SN1 mechanism [1]
- fishy smell of amine disappear [1] - Q is an alcohol [1]
b) i. - 2-amino-3-methylbutanoic acid [1] - Mechanism of the reaction [3]
ii. - high melting point / soluble in water [1]
iii. Each structure [1] x 2 [2]

18. a) - Each structure of S and T [1] x 2 [2] - Equation [1] R [1]

- carbon in S is sp hybridised [1] - Type of reaction : elimination reaction [1]

- carbon in T is sp2 hybridised [1]
- carbon in S has linear shape [1] 20. a) - K has unsaturated C=C / contain alkene [1]
- carbon in T has trigonal planar shape [1] - Structure of K [1] L [1] M [1] [3]
- Since S has 2  bond ; there S form triple bond in between C - reagent and condition of ozonolysis [1]
and C [1] - Equation [1]
- Since T has 3 delocalised  bond ; there are 6 carbon that
has an electron in an unhybrid p orbital [1]
- bond length in CC in S is shorter than C=C in T [1]

b) - [1] - both L and M are carbonyl compound [1]

- equations of L and M with 2,4-DNPH [2]
- white precipitate formed is [1]
- catalyst used in esterification is concentrated H2SO4 [1]

- [1]
- pair of geometrical isomerism [2]
- L contain methyl carbonyl group [1]
- equation with alkaline iodine [1]

- M is an aldehyde with 4 C and oxidise to butanoic acid [1]

- equation [1]

b) - Fehling’s solution / Tollens’ reagent [1]

- M turn blue solution to brick red precipitate / silver mirror
while L shows no observable changes [1]

Section A

1. D C in benzene is sp2 hybridised ; C in q is sp3 hybridised ; O in r is also sp3 hybridised (2 lpe and 2 bpe)
The molecular formula of methyl methacrylate is C5H8O2 ; it does not have optical or geometrical isomers nor it
2. C undergoes condensation poymerisation (it undergoes additional polymerisation) yet it is an isomer of 2-methyl-2-
butenoic acid ; CH3CH=C(CH3)COOH
Nucleophile means love nucleus, therefore contain a lone pair electron to donate, hence Lewis base, and can be
3. C
formed from heterolytic fission. Reaction involving Friedel-craft reaction usually produce electrophile
 ClCH2COOH is a stronger acid than CH3COOH due to inductive effect of Cl, which caused electron density in O
in ClCH2COO- is lower than CH3COO- (pKa of ClCH2COOH is smaller than CH3COOH) and hence O–H in
4. A
ClCH2COOH is easier to dissociate than CH3COOH . As a result ClCH2COO- is weaker conjugate base than
CH3COO- therefore ClCH2COO- is more stable than CH3COO- ;
For alkene to form only a carboxylic acid, it must have only a 20 alkene (A and D wrong) ; when react with HBr,
5. B
B form optical active CH3CHBrCH2CH2CH2CH3.

6. B

7. A Rate of hydrolysis increase in order chlorobenzene < 10 < 20 < 30 therefore A is answer
Due to the presence of cyclohexane, it easily exhibited optical isomerism but not geometrical isomerism ; and its
8. C
easily dissolve in organic solvent ; it has a secondary alcohol
Molecules contain secondary amine (A wrong) ; It is optically active [at the -CH(OH)-] (B wrong) ; Since it does
9. D not have –COOH group, it will not react with Na2CO3 ; and it undergoes dehydration to form 2 different alkenes
(D correct)

I. NaOH II. Br2 (aq) III. FeCl3 KMnO4 / H+

10. C C6H5OH    X
C6H5COOH  X X X

11. A An aldehyde act as reducing agent as well as oxidizing agent.

12. B HCOOCH(CH3)2  HCOOH + (CH3)2CHOH ; HCOOH  CO2 + H2O ; (CH3)2CHOH  CH3COO- + CHI3

Compound is N-(p-hydroxy)phenylethanamide (A wrong) ; which can undergoes hydrolysis in acidic and alkaline
13. A
solution to form 2 organic compound (B and C true) ; due to presence of phenol, it react with Br2 (aq) (D true)

14. D Basicity of amine decrease in the following order : C2H5NH2 > CH3NH2 > NH3 > C6H5NH2
Monomer of polychloroethane is CH2=CHCl ; therefore it can be prepared by
15. D
CH2ClCH2Cl + NaOH (ethanol)  CH2=CHCl