Page 8 June Examination, 2013 CHEM 1030 Chemistry of Materials 1
SECTION B: QUESTIONS IN THIS PART ARE WORTH 1.5 MARKS EACH.
ANSWER ALL QUESTIONS FROM THIS PART.
Circle the correct answer, eg D :
B1 Free radical bromination of an alkane with a halogen
with UV light as catalyst (for example, ethane with
chlorine, right) has three steps:
A: initiation, combination, termination
B: initiation, crosslinking, termination
C: initiation, crystallisation, termination
D: initiation, hydrolysis, termination
E: initiation, propagation, termination
CH3CH3 + Cl2
CH3CH2Cl + HCl
UV
B2 Consider the reaction between an alkyl halide and
cyanide ion (CN), right. The Cl is:
A: an electrophile
B: a free radical
C: the leaving group
D: a nucleophile
E: the substrate
Cl
CN
+ CN
+ Cl
B3 Consider the general reaction to the right, of a
tertiary alkyl halide with hydroxide to form an
alcohol. This is:
A: an elimination
B: a nucleophilic addition
C: a reduction
D: an SN1 nucleophilic substitution
E: an SN2 nucleophilic substitution
C Cl + HO
C OH + Cl
R
R
R
R
R
R
B4 Consider the alcohols on the right:
A: (i) is primary and (ii) is secondary
B: (i) is primary and (ii) is tertiary
C: (i) is secondary and (ii) is primary
D: (i) is secondary and (ii) is tertiary
E: (i) is tertiary and (ii) is primary
(i)
(ii) HO
OH
B5 Consider the three compounds on the right, all
isomers of C4H10O2. The order from lowest boiling
point to highest boiling point is:
A: A, B, C
B: A, C, B
C: B, A, C
D: B, C, A
E: C, A, B
A
B
C
O
HO
OO
OH
OH
CHEM 1030 Chemistry of Materials 1 June Examination, 2013 Page 9
B6 Consider the amines on the right:
A: (i) is primary and (ii) is secondary
B: (i) is primary and (ii) is tertiary
C: (i) is secondary and (ii) is primary
D: (i) is secondary and (ii) is tertiary
E: (i) is tertiary and (ii) is primary
(i)
(ii) HN
NH2
B7 Consider the carbocations to the right. The order,
from least stable to most stable is:
A: A, B, C
B: A, C, B
C: B, A, C
D: B, C, A
E: C, A, B
+
+
+A
B
C
B8 Consider ribulose to the right, a five carbon keto
sugar. This molecule has:
A: no chiral centres, and no stereoisomers
B: one chiral centre, and two stereoisomers
C: two chiral centres, and two stereoisomers
D: two chiral centres, and four stereoisomers
E: three chiral centres, and eight stereoisomers
CH2OH
O
OHH
OHH
CH2OH
ribulose
B9 Consider the compounds to the right. These two
compounds:
A: are enantiomers
B: are diastereomers
C: are not optical isomers
D: have no chiral centres
E: are not isomers
CH3
HHO
OHH
CH3
CH3
OHH
OHH
CH3
B10 Consider the two compounds to the right, flavour
components of cheeses such as camembert and brie.
The reaction to convert compound A to B is best
classed as:
A: alkylation
B: elimination
C: oxidation
D: reduction
E: substitution
O
A
B
OH
(Section B: 1.5 x 10 = 15 marks)
Page 10 June Examination, 2013 CHEM 1030 Chemistry of Materials 1
SECTION C: ANSWER ANY THREE (AND ONLY THREE) QUESTIONS FROM THIS SECTION.
QUESTION C1. ORGANIC NOMENCLATURE
(a) Draw structures for four of the following; use stick figures wherever possible:
3-butoxy-1-propanol 4-isopropyl-3-heptanol
4-tertiary-butyl-4-methylcyclohexanol 1,3-diethoxybutane
trans-1,2-dinitrocyclopropane N-ethyl-N-methyl-2-aminooctane
(b) Give names for two of the following:
HN
HN
F
Cl NO2
OH
F
(6 + 4 = 10 marks)
CHEM 1030 Chemistry of Materials 1 June Examination, 2013 Page 11
QUESTION C2. ISOMERISM
(a) Classify each of the pairs of compounds below as:
a pair of functional group isomers; or a pair of geometric isomers; or
a pair of positional isomers; or a pair of optical isomers; or
a pair of skeletal isomers; or the same, (not isomers).
H H
H
H
and
C
CH3
CH3CH2CH2H
OH
C
CH3
CH3CH2CH2OH
Hand
and
and
OH
O
(b) Draw:
(i) a pair of positional isomers (ii) a meso compound
(6 + 4 = 10 marks)
Page 12 June Examination, 2013 CHEM 1030 Chemistry of Materials 1
QUESTION C3. REACTIONS
(a) Classify each of the following reactions as addition, elimination, oxidation, reduction, substitution,
rearrangement, condensation or hydrolysis:
(i) Cl
+ HClHO
(ii)
Br CN
NC
+ Br
(iii) O OHH2/Pt
(iv) BrHBr
(b) Give the organic products of the following reactions:
(i)
OH
KMnO4
(ii)
H
H2/Pt
O
(c) Give a suitable reagent for each of the following reactions:
(i)
Cl
(ii)
OH
Cl
(4 + 3 + 3 = 10 marks)
CHEM 1030 Chemistry of Materials 1 June Examination, 2013 Page 13
QUESTION C4. MECHANISMS
(a) The reaction between a primary alkyl halide and cyanide ion to give an alkyne goes via an SN2
mechanism. For example, consider the following:
CH3CH2CH2Cl + NCNa+ CH3CH2CH2CN + NaCl
Give the mechanism for the reaction, showing all full and partial positive and negative charges, and
electron movements using curved arrows.
(b) Give the mechanism for the formation of the tertiary butanol from tertiary-butyl chloride and KOH,
assuming the reaction proceeds via an SN1 mechanism. Show all full and partial positive and
negative charges, and electron movements using curly arrows.
(CH3)3CCl + KOH (CH3)3COH + KCl
tertiary-butyl chloride tertiary butanol
substitution
product
(3 + 7 = 10 marks)
(Section C: 3 x 10 = 30 marks)
Page 14 June Examination, 2013 CHEM 1030 Chemistry of Materials 1