TOPIC 10: ORGANIC CHEMISTRY: HALOGENOALKANES, ALCOHOLS AND

SPECTRA

CH3CH2Br + KOH  CH3CH2OH + KBr

What type of reaction is this?

A nucleophilic substitution
B elimination
C reduction
D electrophilic addition

Your answer A

(1)
(Total for Question 1 = 1 mark)

2 Butan-1-ol can be dehydrated to an alkene.

(a) Name the dehydrating agent and conditions used to achieve this dehydration.
(2)
Heated at the High Temperature with concentrated phosphoric acid

(b) Butan-1-ol can be halogenated using phosphorus pentachloride.

(i) Write a balanced reaction equation.
(2)
CH3CH2CH2CH2OH + PCl5  CH3CH2CH2CH2Cl+POCl3+HCl

(ii) Name the two by-products of this reaction.

(2)
Phosphoryl chloride , hydrogen chloride

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 (iii) Name the type of reaction mechanism involved.
(1)
Halogenation

(Total for Question 2 = 7 marks)

3 Alcohols may be oxidised by heating with acidified potassium dichromate(VI).

(a) Write a balanced equation to show the oxidation of propan-1-ol under
distillation conditions.
(1)
CH3CH2CH2OH + [O]  CH3CH2CH2CHO + H2O

(b) Propan-2-ol may also be oxidised by acidified potassium dichromate(VI)

under these conditions. Describe a laboratory test to distinguish between
the organic product from part (a) and the organic product from the oxidation
of propan-2-ol.

heat with Fehling’s solution (2)

Aldehyde ( a ) shows the change in colour from blue to red
In contrast, ketone ( oxidation of propan-2-ol) doesn’t show any
change in colour
(Total for Question 3 = 3 marks)

The table below shows infrared absorption ranges associated with some organic
functional groups. Use these data to help you answer the following questions.

Bond stretching Wavenumber range/cm–1

C–H in alkanes 2962–2853
C–H in alkenes 3095–3010
C–H in aldehydes 2900–2820
2775–2700
C=C in alkenes 1669–1645
O–H in alcohols 3750–3200
C=O in aldehydes 1740–1720
C=O in ketones 1720–1700
C=O in carboxylic acids 1725–1700
O–H in carboxylic acids 3300–2500
N–H in amines 3500–3300

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4 Look at the infrared spectrum below.

Which of the following type of substance could have produced this spectrum?
A an alcohol
B a carboxylic acid
C a ketone
D an aldehyde

Your answer A

(1)
(Total for Question 4 = 1 mark)

5 Propanone and propanal are isomers of C3H6O and both contain C=O groups.
Which of the following statements is not correct?

A The fingerprint regions in their IR spectra will have very different patterns.
B They will both strongly absorb IR radiation in the region 2775–2700 cm–1.
C Their carbonyl groups will absorb IR radiation in very similar wavenumber
ranges.
D They will both strongly absorb IR radiation in the region 1725–1700 cm–1.

Your answer D

(1)
(Total for Question 5 = 1 mark)

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6 Propan-1-ol and propan-2-ol are position isomers.

(a) Which of these features would be seen in the mass spectra and IR spectra
of propan-1-ol and propan-2-ol?

m/z of the molecular ion in Absorbance at 3750–3200 cm–1

mass spectrum in IR spectrum
A different in both
B different only in one
C same in both
D same only in one

Your answer C
(1)

(b) The fragmentation pattern in the mass spectrum of propan-1-ol will be

different from the one in the mass spectrum of propan-2-ol.
At what m/z ratio will there be a major peak for propan-1-ol but not for
propan-2-ol?

A 15
B 31
C 45
D 59

Your answer B

(1)
(Total for Question 6 = 2 marks)

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7 The diagram shows the mass spectrum of a carboxylic acid.

(a) State the m/z of the molecular ion.

(1)
60

(b) Give the name and structural formula of this carboxylic acid.
(2)
RCOOH  60 – (12+16X2+1)=15  CH3  CH3COOH  Ethanoic Acid

(c) Give the formula of the species responsible for the peak at m/z = 15.
(1)
CH3

(d) Which functional group is responsible for the broad stretching absorption
seen in the infrared spectra of these compounds?
(1)
O – H Carboxylic Acid

(Total for Question 7 = 5 marks)

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8 Give the IUPAC names for the following structures:

b)
a) b)

2,4 - Dimethylpent-1-ol & 2 – Methylpentan-3-one

…………..…………………………………………….……………………………………

9 Consider an alcohol with a molecular formula of C4H10O.

a) Draw the structure of a primary alcohol with the above formula

b) Draw the structure of a secondary alcohol with the above formula

c) Draw the structure of a tertiary alcohol with the above formula

TOTAL FOR ASSESSMENT = 25 MARKS

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