Question 1

Compound X produces a carboxylic acid when heated under reflux with acidified potassium dichromate (VI). Compound
X has no reaction with sodium metal.
What could be the identity of compound X?
A. Propanal
B. Propanone
C. Propan-1-ol
D. Propan-2-ol

Question 2
Considering only structural isomers, what is the number of alcohols of each type with the formula C5H12O?
Primary Secondary Tertiary

A 3 3 2
B 4 2 2
C 4 3 1
D 5 2 1
Question 3
Which sequence of reagents may be used in the laboratory to convert propan-1-ol into 2-bromopropane?
A. Concentrated sulfuric acid, followed by bromine
B. Concentrated sulfuric acid, followed by potassium bromide
C. Ethanolic sodium hydroxide, followed by bromine
D. Ethanolic sodium hydroxide, followed by potassium bromide
Question 4
Which diagram gives the skeletal formula of 4-chloropentan-2-ol?
A.

B.

C.
 D.

Question 5
Which alcohol has a chiral centre and can be oxidised to a ketone?
A. Pentan-2-ol
B. Pentan-3-ol
C. 3-methylhexan-1-ol
D. 3-methylhexan-3-ol

Question 6
Which reaction will distinguish between a primary and a secondary alcohol?
A. Warming with H+ / MnO4-
B. Warming with H+ / Cr2O72-
C. Dehydration, followed by reaction with Br2 (aq)
D. Oxidation, followed by reaction with Fehling’s (or Tollens’) reagent
Question 7
An alcohol with molecular formula CnH2n+1OH has a chiral carbon atom but does not react with hot, acidified K2Cr2O7.
What is the smallest possible value for n?
A. 5
B. 6
C. 7
D. 8

Question 8
Buta-1,3-diene is currently obtained from fossil fuel sources. In future it may be obtained from ethanol, which can be
produced from non-food agricultural crops. The sequence of reactions is as follows.

Which term could be used to describe step 1?

A. Condensation
B. Dehydration
C. Dehydrogenation
D. Hydrogenation
Question 9
The functional group in a primary alcohol is –CH2OH.
Which reagent reacts with a primary alcohol, under suitable conditions, to give an organic product with the same number
of oxygen atoms as the alcohol?
A. Al2O3
B. CH3CO2H
C. HBr
D. Na
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