ScoreChem962/3_set 5

1. What is the product when propene is
oxidised with cold dilute potassium
manganate(VII)?
A CH3CH(OH)CH2OH
B CH3CH2CH2OH
C CH3CH2CHO
D CH3COCH3

2. The structural formula of a compound is as
follows.
CH3C = CHCH2CHCH2CHO
| |
CH3 CH3
What is its IUPAC name?
A 2,5-dimetylhept-2-enal
B 3,6-dimetylhept-2-enal
C 2,5-dimetylhept-5-enal
D 3,6-dimetylhept-5-enal

3. How many total alkenes (including
stereoisomers) are possible for the product of
the following reaction?
heat
CH3 CH(CH3) CHBr CH2CH2CH3  ALKENES
alcoholic KOH
A 2 B 3
C 4 D 5

4. Which of the following species can act as a
nucleophile?
A  CH3 B Br+
C AlCl3 D CN-

5. Which of the following reagent is used to
distinguish phenol from phenylmethanol?
A Ethanoyl chloride
B Chloroethane
C Bromine water
D Iodine solution

6. Which pair of reagents cannot be used to
prepare CH3CH2Cl?
A CH2 = CHCl + H2
B CH3CH2OH + HCl
C CH3CH2OH + Cl2
D CH3CH2NH2 + Cl2

7. Z , with a formula of
gives an orange precipitate with 2,4-DNPH
reagent, no precipitate with Fehling’s solution
and no reaction with phosphorous
pentachloride. It contains a chiral carbon atom.
The C4H7O group in the molecule Z could be
HO C4H7O
A CH2 = C – CH(OH)CH3
|
O = C – CH(CH3) CH3
|
CH3 – CH CO CH3
|
CH3 – C(CH3) CHO
|
B
C D

8. Which of the following compounds reacts
easily with cold water?
Cl
CH2Cl CH3CH2 Cl
CH3CH2 COCl
A B C
D

9. What is the principal product from the
following series of reactions?
LiAlH4 PBr3 KCN LiAlH4
   
Ether Alcohol Ether Ether
heat
COOH
CH2NH2
CH2 CH2 NH2 CH2CONH2
CH2CH(OH)NH2
A
C
B
D

10. Which of the following is not true for
proteins?
A They are natural condensation polymers
B They are built up from identical
monomer units
C They are able to be hydrolysed
D They are built up from amino acids

11. Adrenaline has the following formula
Which of the following statements about
adrenaline is correct?
A It is a primary amine
B It is chiral and contains three alcohol
groups
C It is chiral and contains two phenol
groups
D It exhibits cis-trans isomerism
HO CH(OH)CH2NHCH3
HO

12. Nylon-6,6 can be made by condensation
polymerisation of a compound X and hexane-
1,6-diamine.
-(--- N – C – (CH2)4 – C – N – (CH2)6 – N – C ---)-
| || || | | ||
H O O H H O
Compound X could be
A hexane-1,6-diol
B hexanedioyl chloride
C potassium hexanedioate
D hexanoic acid

13. The principle product formed when hydrogen
iodide reacts with prop-1-ene is 2-iodopropane
rather than 1-iodopropane. Which of the
following statements is correct regarding this
observation?
A Production of 2-iodopropane proceeds at a
higher rate than that leading to the
production of 1-iodopropane
B Production of 2-iodopropane proceeds via
a primary carbonium
C Production of 2-iodopropane proceeds via
a secondary carbonium
D 2-iodopropane is more stable than 1-
iodopropane

14. The organic compounds which are expected
to decolourise bromine water include
I CH3CH = CH COOH
II CH3CH(OH) CH2CH3
III C6H5 – OH
A I and II B I and III
C II and III D I, II and III

15. Which of the following statements suggests
the presence of free radicals in the
bromination of methylbenzene?
I The reaction proceeds most quickly
in sunlight
II Hydrogen bromide is present in the
product
III Bromomethylbenzene is formed as
the first product
A I only B I and II
C I and III D II and III

Q16 [8 marks]
(a) Paracetamol and aspirin have analgesic
(pain killing) action and are readily absorbed
from the intestines.
CH3CONH OH
COOH
O – C – CH3
O
Paracetamol Aspirin
Each drug is easily hydrolysed by enzymes in
the intestine. For each drug, name the group
which is hydrolysed. [2 marks]

(b) Adrenalin is a hormone which, when
secreted directly into the bloodstream, acts as a
stimulant. It has the structure as below.
HO
HO
CH – CH2 – NHCH3
OH
(i) Name three functional groups present
in the adrenalin molecule. [3 marks]
(ii) By means of asterisk, identify the
chiral centre in the structure of adrenalin
drawn above. [1 mark]
Q16

HO
HO
CH – CH2 – NHCH3
OH Adrenalin
(iii) The synthesis of adrenalin includes the
following stages:
HO
HO
CHO A B Adrenalin
Give the full structure formulae of A and B.
[2 marks]
Q16
HCN H2, Ni

Q17 [7 marks]
(a) H2N – CH(CH3)COOH H2N – CH2COOH
Alanine Glycine
(i) Name the functional groups present
in the amino acids given above. [2 marks]
(ii) Draw the structure of the zwitterions
for alanine. [1 mark]
(iii) Write a reaction equation to show
what would happen when alanine dissolves in
hydrochloric acid. [1 mark]
(iv) Draw one structural formula for the
dipeptide formed between alanine and glycine.
[1 mark]

Q17
(b) The synthetic rubber SBR is a copolymer
of styrene (phenylethene) and buta-1,3-diene
in the ratio of 3 : 1.
(i) Draw the structure of SBR. [1 mark]
(ii) What is the type of polymerisation
used to produce SBR? [1 mark]

Q16
A B
HO
HO
CHCN
OH
(a) Paracetamol = amide, aspirin = ester
(b)(i) Phenol, Hydroxy, Amino
(ii) – *CH(OH) – CH2 – NHCH3
(iii)
HO
HO
CHCH2NH2
OH

(a) 1 amino group
2 carboxyl group
3 +H3N – CH(CH3) COO –
4 H2N-CH(CH3)COOH + HCl
 ClH3N- CH(CH3)COOH
5 H2N – CH(CH3) – CONH – CH2COOH
OR H2N – CH2 – CONH – CH(CH3)COOH
6 [peptide link] C – N
|| |
O H
(b)1 --(-- CH – CH --)3-(-- CH2CH = CHCH2 --)--
2 addition polymerization
Q17

SECTION C
ARE YOU REALLY READY??

Q18
An organic compound, Z, has the following
composition by mass:
C, 62.1% H, 10.3% O, 27.6%
(a) Determine the empirical formula of Z.
[3 marks]
(b) Z has three isomers, E, F and G. E is an
alcohol, F is a ketone and G is an aldehyde.
Draw possible structural formulae for E, F and
G. [3 marks]

Q18
(c) Describe tests that would allow you to
show that:
(i) E is an alcohol, whereas F and G are
not, [3 marks]
(ii) F and G are carbonyl compounds,
whereas E is not, [3 marks]
(iii) G is aldehyde, whereas E and F are
not. [3 marks]

Q19
(a)
Dopamine
(i) Draw a structure of the product formed
when dopamine reacts with warm dilute nitric
acid. [1 mark]
(ii) Explain any type of reaction which takes
place. [4 marks]
HO CH2CH2NH2
HO

(b) Dopamine can be synthesised from the
following compound.
Outline a scheme of reactions illustrates
the synthesis of dopamine. State reagents and
conditions required. [5 marks]
HO CH3
HO

(c) Compounds R and S are two isomers with
molecular formula C8H10O. R gives off white
fumes with thionyl chloride and forms a yellow
precipitate with alkaline aqueous iodine but S
does not. S dissolves in aqueous potassium
hydroxide but R does not.
Explain the above observations and write
the structural formulae of R and S.
[5 marks]

(a)
Element C H O
1 moles of 62.1/12.0 10.3 /1.0 27.6 /16.0
2 Ratio 3 6 1
3 empirical formula C3H6O
(b)
1 E CH2 = CH CH2OH OR CH2 = C(OH) CH3
2 F CH3 CO CH3
3 G CH3CH2CHO
Q18

(C) [9 marks]
1,2 [E=alcohol] PCl5 r.t. / Na, r.t.
3 white fumes, HCl / effervescence occurs, H2 
4,5 [F, G=carbonyl]
2,4-dinitrophenylhydrazine, heat
6 orange ppt
7,8 [G=aldehyde] Tollen’s reagent, heat
/ Fehling solution, heat
9 silver mirror / reddish brown ppt formed
Q18

Q19
1
2 acid – base reaction / neutralisation
3 NH2 (amino) group is basic due to the lone
pair electrons on N
4 electrophilic substitutions
5 OH (phenol) group activates the benzene ring /
benzene ring is richer in electron density
/ lone pair electrons from O delocalized into
benzene ring
HO CH2CH2NH3
+
HO NO2
NO2O2N

Q19
(b) [5 marks]
1 Cl2, UV
2 [product] - CH2Cl
3 KCN / alcohol, reflux
4 [product] - CH2CN
5 H2, Ni, 180C /
LiAlH4 in dry ether followed by acidic
hydrolysis

(c) [5 marks]
1 [R gives off white fumes with SOCl2]
R has OH group / R is an alcohol
2 [R forms yellow ppt with I2/NaOH]
R has a structure of – CH(CH3)OH
3 [S dissolves in KOH]
S is acidic / S is a phenol
4 R is C6H5 – CH(OH)CH3
5 S is HO – C6H4 – CH2CH3 or
HO – C6H3 – (CH3)2
Q19

Sigh! Why didn’t I
study hard from
the beginning??
YES!!
I GOT IT.

ScoreChem962/3_set 5

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