Department of Chemistry

Grade 12

Class Test IV

Topic: Further organic chemistry

Name:___________________________________________________

Class:______________________

Total for the Paper: 50 Marks

Duration: 1 hour

Section A
Answer ALL the questions in this section. You should aim to spend no more than 10 minutes on this
section. For each question, select one answer from A to D and put a cross in the box
. If you change
your mind, put a line through the box
and then mark your new answer with a cross
.

1 Which of the following shows the correct order of decreasing boiling temperature?
A Propanoic acid, propan-1-ol, propanal
B Propan-1-ol, propanal, propanoic acid
C Propanal, propanoic acid, propan-1-ol
D Propanicacid, propanal, propan-1-ol
(Total for Question 1 = 1 mark)
2 A carbonyl compound with molecular formula C6H12O reacted with iodine in an
alkaline solution to give a pale yellow precipitate with an antiseptic smell.
The carbonyl compound is
A CH3CH2CH2CH2CH2CHO
B CH3CH(CH3)CH2COCH3
C CH3CH2C(CH3)2CHO
D CH3CH2CH2COCH2CH3
(Total for Question 2 = 1 mark)
3 Which of the following can form butanoic acid in a single step reaction?
A 1-chlorobutane
B butanenitrile
C butan-2-ol
D but-1-ene
(Total for Question 3 = 1 mark)

Dept. of Chemistry/VIHS/Class Test IV/2014

4 The ester, methyl propanoate, can be made in a single step from

A CH3OH and CH3CH2CHO
B CH3OH and CH3CH2COCl
C CH3CH2OH and CH3COCl
D CH3CH2OH and CH3CHO
(Total for Question 4 = 1 mark)

5 The repeat unit of the polymer formed from HOCH2CH2CH2OH and HOOCCH2COOH is
A -OCH2CH2CH2OOCCH2COB -OCH2CH2COCH2COOC -OCH2CH2CH2COOCH2COD -OCH2CH2COOCH2CO(Total for Question 5 = 1 mark)
6 The compound bromochlorofluoromethane, CHClBrF, has a chiral carbon atom and exists as a pair of
enantiomers.
The enantiomers will have different
A colours.
B effects on plane-polarized light.
C chemical reactions.
D boiling temperatures.

(Total for Question 6 = 1 mark)

7 Which of the following statements about ethanoyl chloride is not correct?
A It reacts with ammonia to make an amine.
B It reacts with an amine to make an amide.
C It reacts with an alcohol to make an ester.
D It reacts with water to make an organic acid.
(Total for Question 7 = 1 mark)

Dept. of Chemistry/VIHS/Class Test IV/2014

8 In gas chromatography, mixtures are passed through a long tube containing a liquid as the stationary
phase. The mixtures are separated into their components because the components differ in
A relative molecular mass.
B melting temperature.
C volatility.
D force of attraction to the liquid.
(Total for Question 8 = 1 mark)
9 An organic compound, Y, has the molecular formula C6H12O.
(a) The infrared spectrum of compound Y includes a strong absorbance at 1730 cm1
but has no broad absorbance at 37503200 cm1.
Refer to pages 5 and 6 of the Data Booklet.
The compound could be
A an alcohol, aldehyde or ketone.
B a ketone but not an alcohol or aldehyde.
C an aldehyde but not an alcohol or ketone.
D an aldehyde or a ketone but not an alcohol.
(b) Compound Z is an isomer of Y and has the structure shown below
CH3CH2CH2COCH2CH3
The high-resolution proton nmr spectrum for compound Z shows five peaks.
The splitting patterns in these peaks are likely to be
A 1 quartet, 3 triplets and 1 sextuplet (split into six).
B 1 quartet, 1 doublets, 2 triplets and 1 sextuplet (split into six).
C 2 singlet, 2 doublets and 1 triplet.
D 2 doublets, 2 triplets and1 sextuplet (split into six).
(Total for Question 9 = 2 marks)
TOTAL FOR SECTION A = 10 MARKS

Dept. of Chemistry/VIHS/Class Test IV/2014

SECTION B
Answer ALL the questions. Write your answers in the spaces provided.
10 (a) ethanal can be converted into N-ethyl ethanamide, CH3CONHCH2CH3, in three steps.
CH3CHO
Step1
CH3COOH
Step2
Compound X
Step 3
CH3CONHCH2CH3
(i) Suggest the reagents and the observation, if any, made in step1

(2)

Reagent:...............................................................................................................................................................
Observation:.........................................................................................................................................................
..............................................................................................................................................................................
(ii) The reagent used in Step 2 is phosphorus(V) chloride, PCl5.
Identify, by name or formula, compound X

(1)

..............................................................................................................................................................................
(iii) steamy or misty white fumes are observed in step 2. Identify, by name or formula of the substance
which gives this observation and give a further test to confirm it.

(2)

..............................................................................................................................................................................
..............................................................................................................................................................................
..............................................................................................................................................................................
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(iv) Identify, by name or formula, the reagent needed for Step 3.

(1)

..............................................................................................................................................................................

(v) State the number of peaks you would expect in the low resolution proton nmr spectrum of N-ethyl
ethanamide.

(1)

..............................................................................................................................................................................
Dept. of Chemistry/VIHS/Class Test IV/2014

(b) (i) Write the equation for the reaction between ethanoic acid and propan-2-ol, in the presence of an acid
catalyst, showing the structure of the organic product.
State symbols are not required.

(2)

..............................................................................................................................................................................
(ii) Even with the use of a catalyst, this reaction is quite slow and incomplete. Suggest a reagent, to replace
the ethanoic acid, which would form the same product at a faster rate.
Suggest two reasons why your chosen reagent reacts faster.

(3)

(c) A sample of ethanoic acid was reduced to form compound Q.

The infrared spectrum of compound Q is shown below.

Use the infrared spectrum to identify compound Q. Refer page 5 of the data booklet.
Explain your reasoning, quoting suitable data.

(2)

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(Total for Question 10 = 14 marks)

Dept. of Chemistry/VIHS/Class Test IV/2014

11 (a) Compound A, HCOOCH2CH2CH3, is an ester. Name this ester and write an equation for its
reaction with aqueous sodium hydroxide.

(3)

Name....................................................................................................................................................................
Equation...............................................................................................................................................................
(b) A naturally-occurring triester, shown below, was heated under reflux with an excess of aqueous
sodium hydroxide and the mixture produced was then distilled. One of the products distilled off
and the other was left in the distillation flask.
CH 3 (CH 2 )16 COOCH 2
CH 3 (CH 2 )16 COOCH
CH 3 (CH 2 )16 COOCH 2

(i) Draw the structure of the product distilled off and give its name.

(2)

Structure

Name...............................................................................................................................................
(ii) Give the formula of the product left in the distillation flask and give a use for it.

(2)

Formula.........................................................................................................................................
Use ...............................................................................................................................................
(Total for Question 11 = 7 marks)

12 Consider the reaction scheme below, which shows how the compound methyl methacrylate,
Dept. of Chemistry/VIHS/Class Test IV/2014

CH2=C(CH3)COOCH3, is prepared industrially from propanone.

(a) (i) State the type of reaction which occurs in Step 2.

(1)

............................................................................................................................................................................
(ii) Name the reagent in Step 2.

(1)

.............................................................................................................................................................................
(iii) State the type of reaction which occurs in Step 3.

(1)

..............................................................................................................................................................................
(iv) State the type of reaction which occurs in Step 4

(1)

..............................................................................................................................................................................
(v) Give then organic reagent required for Step 4.

(1)

..............................................................................................................................................................................
(b) (i) Give the mechanism for the reaction in Step 1 between the hydrogen cyanide and propanone.

(3)

(ii) The reaction in (b)(i) is carried out at a carefully controlled pH. Given that hydrogen cyanide is a weak
acid, suggest why this reaction occurs more slowly at both high and low concentrations of hydrogen ions.
Dept. of Chemistry/VIHS/Class Test IV/2014

(2)
High H+ concentration
..............................................................................................................................................................................
..............................................................................................................................................................................
Low H+ concentration
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(Total for Question 12 = 10 marks)
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13 Citronella oil is obtained from lemongrass.
It is a source of chemicals for the perfume industry.
Three of the aldehydes found in citronella oil are shown below.

citronellal

geranial

neral

neral

(a) Give the molecular formula for geranial.

(1)

..............................................................................................................................................................................
(b) Citronellal has one chiral carbon atom.
(i) define the term chiral

(1)

(ii) Draw a circle around the chiral carbon atom on the structure of citronellal below.
Dept. of Chemistry/VIHS/Class Test IV/2014

(1)

(c) Geranial and neral are a pair of E-Z isomers.

(i) Explain how this type of isomerism arises.

(2)

..............................................................................................................................................................................
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..............................................................................................................................................................................
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..............................................................................................................................................................................

(ii) Draw a circle around any part of the geranial structure below that causes its E-Z isomerism.

(1)

(d) Describe a simple test tube reaction to show that these three carbonyl compounds are aldehydes and not
ketones. State the observation you would make.

(2)

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..............................................................................................................................................................................
..............................................................................................................................................................................
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(e) The skeletal formula of neral is shown below.

Draw the skeletal formula for the organic product of the reaction of neral with
(i) excess hydrogen in the presence of a nickel catalyst.

(1)

Dept. of Chemistry/VIHS/Class Test IV/2014

(ii) lithium tetrahydridoaluminate(III) (lithium aluminium hydride) in dry ether.

(1)

(Total for Question 18 = 10 marks)

_______________________________________________________________________________________

Dept. of Chemistry/VIHS/Class Test IV/2014

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