2.
3.
4.
CfE Advanced Higher Chemistry
Unit 2 Synthesis
SECTION 1
1. Propene can be produced by heating 1-bromopropane with ethanolic potassium hydroxide.
This reaction is an example of
A
B
C
D reduction hydrolysis elimination condensation.
A
B
C
D
A
B
C
D
The formula C
4
H
10
O could represent an alcohol (C
4
H
9
OH) or an ether (C
2
H
5
OC
2
H
5
).
Which of the following statements would not be true about both compounds?
They can be made by nucleophilic substitution from a haloalkane.
They have hydrogen bonds between their molecules.
They are used as solvents.
They are flammable.
Which of the following will react to form CH
3
CH
2
OCH
2
CH
2
CH
3
?
CH
3
CH
2
CH
3
CH
2
OH and CH
3
CH
2
CH
2
OH and CH
3
COONa
COONa
CH
3
CH
2
ONa and CH
3
CH
2
CH
2
I
CH
3
CH
2
ONa and CH
3
CHICH
3
Which of the following structures represents a tertiary amine?

5.
6.
7.
CfE Advanced Higher Chemistry
Unit 2 Synthesis
Which of the following is not an example of a hydrolysis reaction?
A
B
C
2
H
4
+ H
2
O → C
2
H
5
OH
CH
3
CN + 2H
2
O → CH
3
COOH + NH
3
C CH
3
COOCH
3
+ H
2
O → CH
3
COOH + CH
3
OH
D C
6
H
5
COOCH
3
+ H
2
O → C
6
H
5
COOH + CH
3
OH
The conversion of butanoic acid into butan-1-ol is an example of
A
B
C
D elimination substitution oxidation reduction.
Which line in the table is correct for the types of reaction taking place at ①
,
② and
③ .
Reaction ① Reaction ②
A substitution
B substitution
C
D addition addition elimination reduction reduction elimination
Reaction ③ substitution substitution condensation substitution
8. The major product in the reaction of HCl with 2-methylpent-2-ene, is
A
B
2-chloro-2-methylpentane
3-chloro-2-methylpentane
C
D
2,3-dichloro-2-methylpentane
4-chloro-4-methylpentane.
9.
A
B
C
D
Which of the following reacts with ethanol to form the ethoxide ion?
Na(s)
Na O(s)
2
NaCl(aq)
NaOH(aq)

CfE Advanced Higher Chemistry
Unit 2 Synthesis
10. Bromine reacts with propene to produce 1,2-dibromopropane.
A possible intermediate in the reaction is
11. Which of the following compounds would be expected to have the highest boiling point?
A
B
C
D
Pentanal
Pentan-2-ol
Pentan-2-one
Ethoxypropane
12.
Which species initially attacks the benzene molecule in the above reaction?
A
B
C
D
NO
NO
NO
2
3
–
2
+
HSO
4
–

CfE Advanced Higher Chemistry
Unit 2 Synthesis
13.
The above reaction is an example of
A
B
C
D addition oxidation elimination substitution.
Questions 14 and 15 refer to the following
14. Which of the above involves homolytic fission?
15. Which of the above involves electrophilic substitution?
16. Alkenes may not be prepared by
A
B
C
D thermal cracking of alkanes partial hydrogenation of alkynes dehydration of primary alcohols direct synthesis from carbon and hydrogen.

CfE Advanced Higher Chemistry
Unit 2 Synthesis
17. When but-1-ene reacts with hydrogen choride, 1-chlorobutane and 2-chlorobutane are formed. According to Markovnikov's rule
A
B there will be more of the 2-chlorobutane than the 1-chlorobutane there will be more of the 1-chlorobutane than the 2-chlorobutane
C there will be equal proportions of both products
D it is impossible to tell the relative proportions of each product.
18. Which of the following is most reactive as a nucleophile?
A
B
Br
2
CH
3
C NH
4
I
+
D NH
3
19. Hydrogen bonding occurs in
A
B
CH
3
CH
3
OH
C
D
CH
3
OCH
3
CH
3
CH
2
CHO
.
20. A compound, X, reacts with the product of its own oxidation to form an ester.
X could be
A
B propanal propan-1-ol
C
D propan-2-ol propanoic acid.
SECTION 2
1. Aromatic compounds are widely used in the production of pigments, antioxidants and agrochemicals. The reaction sequence below starts with benzene.
The first step in the sequence produces methyl benzene.
(a) Name reagent A.
(b) Identify catalyst B.
(c) What name is given to the type of reaction taking place in both steps?
1
1
1

2.
CfE Advanced Higher Chemistry
Unit 2 Synthesis
In the reaction sequence shown, 2-chloropentane reacts with sodium hydroxide in different ways depending on the solvent used.
3.
Outline the mechanism for the S
N
2 reaction using structural formulae. 2
(a) Identify:
(i) reagent X;
(ii) reagent Y.
(b) Draw a structural formula for compound A.
(c)
1
1
1
Name a type of chemical reaction involved in the conversion of propanone. 1

4.
CfE Advanced Higher Chemistry
Unit 2 Synthesis
2-Methoxy-2-methylpropane is a compound added to unleaded petrol as a
“knock inhibitor”
It can be synthesised by the reaction of methoxide ions with 2-chloro-2-methylpropane.
(a)
(b)
To which class of organic compounds does 2-methoxy-2-methylpropane belong? 1
How can the methoxide ion be prepared from methanol? 1
(c) The preparation of the 2-methoxy-2-methylpropane proceeds by a S
N
1 mechanism.
(i) Clearly showing the electron shifts, outline the step(s) involved. 2
(ii) Suggest why this reaction is more likely to proceed by a S
N
1 mechanism
rather than a S
N
2. 1
5. When sodium hydroxide solution was added to 2-bromomethylpropane an S
N took place producing methylpropan-2-ol and hydrobromic acid.
1 reaction
(a) (i) What is meant by an S
N
1 reaction? 2
(ii) Draw the structure of the carbocation intermediate formed in this reaction. 1
(b) Chloromethane reacts with sodium ethoxide in an S
N
2 reaction.
(i) How is sodium ethoxide prepared in the laboratory?
(ii) Name the organic product of this S
N
2 reaction.
1
1
6. Myrcene belongs to a large group of compounds known as
terpenes.
Myrcene undergoes addition with excess hydrogen bromide.
Assuming that the addition follows Markovnikov’s rule, draw the structural formula of the product. 1