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