CONFIDENTIAL HS/APR2009/ENV123

UNIVERSITI TEKNOLOGI MARA

FINAL EXAMINATION

COURSE INTRODUCTION TO ORGANIC CHEMISTRY

COURSE CODE ENV123
EXAMINATION APRIL 2009
TIME 2 HOURS

INSTRUCTIONS TO CANDIDATES

1. This question paper consists of two (2) parts : PART A (50 Questions)
PART B (4 Questions)

2. Answer ALL questions from all two (2) parts :

i) Answer PART A in the OMR Multiple Choice Answer Sheet.

ii) Answer PART B in the Answer Booklet. Start each answer on a new page.
3. Do not bring any material into the examination room unless permission is given by the
invigilator.

4. Please check to make sure that this examination pack consists of:

i) the Question Paper

ii) an Answer Booklet - provided by the Faculty
Hi) an OMR Multiple Choice Answer Sheet - provided by the Faculty

DO NOT TURN THIS PAGE UNTIL YOU ARE TOLD TO DO SO

This examination paper consists of 16 printed pages
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CONFIDENTIAL 2 HS/APR2009/ENV123

PART A (50 marks)

Answer ALL questions.

Choose the MOST appropriate for each question.

1. Select the correct name for the following compound.

CH3CH2CHCH = CHCH3
I
CH3

A. 4-ethyl-3-pentene.
B. 4-methyl-2-hexene.
C. 3-methyl-4-hexene.
D. 2-ethyl-3-pentene.

2. What is the molecular formula for the compound: 2, 3-dimethyl-1 -pentanol?

A. C7H140
B. C7H150
C. CeHieO
D. C7H160

3. Which of the following alkanes has five carbon atoms?

A. n-butane
B. 2-methylpropane
C. 2-methylbutane
D. 2, 2-dimethylbutane

4. The formulas of butane and hexene differ by:

A. 2 carbon atoms and 2 hydrogen atoms.

B. 2 carbon atoms.
C. 2 carbon atoms and 4 hydrogen atoms.
D. 3 carbon atoms and 2 hydrogen atoms.

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5. What is the main product of the following reaction?

CH3CH = CH2 + HBr ->

A. CH3CH2CH3
B. CH3C(Br) = CH 2
C. CH3CH(Br)CH2Br
D. CH3CH(Br)CH3

6. Which of the following is a common property of 1-pentanol and 2-pentanol?

A. Both can be oxidized to form ketones.

B. Both have the same boiling point.
C. Both have a hydroxyl group.
D. Both are primary alcohols.

7. Choose the correct reaction type for the following process.

CH3CH2CH2OH + HBr -> CH3CH2CH2Br + H 2 0

A. Dehydration
B. Addition
C. Hydrohalogenation
D. Substitution

8. What is the IUPAC name for the compound:

CH 3 — CH — CH 2 — CH — CH3
I I
CH2CI CI

A. 2, 5 dichloro-4-methylpentane.
B. 1,4-dichlorohexane.
C. 1,4-dichloro-2-methylpentane.
D. 1,4-dichloro-2-methylhexane.

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9. Which of the following statements is TRUE for compounds P and Q given below?

P. CH3CHCH2CH2CH3 Q. CH3CH CHCH3

I I I
CH3 CH3 CH 3

A. They are isomers.

B. They are different formulas of the same compounds.
C. They are compounds from different homologous series.
D. They are different compounds that are not isomers.

10. Alcohols undergo many types of reactions. Which of the following reactions is NOT
undergone by the alcohol functional group?

A. Dehydration
B. Addition
C. Esterification
D. Substitution

11. Which of the following compounds readily decolourises aqueous bromine solution?

A. C2H4
B. C3H8
C. CH3OH
D. CH3NH2

12. Which of the following equations is a substitution reaction for ethane?

A. 2C2H6 + 70 2 -» 4C0 2 + 6H 2 0
B. C2H6 + Cl2 -> C2H5CI + HCI
C. C 2 rl4 + Cl 2 —> C 2 ri4CI 2
D. C 2 rl6 —* C 2 ri4 + H2

13. Which of the following compounds is a secondary alcohol?

A. CH3CH2CH2C(CH3)2OH
B. CH3CH2CH2OH
C. CH3CH2CH(OH)CH2CH3
D. CH3CH2CHO

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14. What is the product of the reaction between 1-hexene, C6H12 and H2?

A. Cyclohexane
B. Benzene
C. n-hexane
D. 2-methylpentane

15. is an alkyl halide.

A. Vinyl chloride
B. 2-chloro-2-methylpropane
C. Benzyl chloride
D. Sodium chloride

16. Which of the following substances is NOT a polymer?

A. Fat
B. Protein
C. Polythene
D. Nylon

17. What is the name for an acid-catalysed reaction between an alcohol and a carboxylic
acid?

A. Esterification
B. Addition
C. Substitution
D. Dehydration

18. Which of the following organic compounds families does NOT contain a carbonyl
carbon?

A. Amides.
B. Aldedyhes.
C. Amines.
D. Carboxylic acids.

19. Which of the following compounds forms a weak acidic solution in water?

A. C2H5OH
B. CH3CH(CH3)COOH
C. CH3CH2CHO
D. C2H5CI

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CONFIDENTIAL 6 HS/APR 2009/ENV123

20. What is the common name for trichloromethane?

A. Chloroform.
B. Methyl chloride.
C. Isopropyl chloride.
D. Methylene chloride.

21. What is the IUPAC name for the compound given below?

H H H H
I I I I
H— C— C — C — C = 0
I I
H H

H—C—H
I
H—C—H
I
H

A. 3-ethylbutanal
B. 2-ethylbutanone
C. 2-methyl-1-pentanol
D. 3-methylpentanal

22. Which of the following compounds undergoes addition polymerisation?

A. CH3CH2CH3
B. CH3CH2CHCH2
C. CH3CH2CHCI2
D. CH3CH2CH2OH

23. What is the name of the homologous series for the compound HCOOH?

A. Alcohol.
B. Aldehyde.
C. Carboxylic acid.
D. Ketone.

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24. Which of the following compounds undergoes dehydration with concentrated sulphuric
acid to produce the alkene CH3CH2CH = CHCH3?

A. CH3CH2CH2CH2CH2—OH
B. CH3CH2CH2CHCH3
I
OH
C. (CH 3 ) 2 CHCH 2 —OH
D. CH3CH2CH2CH2C = O

25. Which of the following statements is FALSE for members of a homologous series?

A. They show similar chemical properties.

B. They show a gradual change of physical properties.
C. They are isomers.
D. They may be prepared by similar methods.

26. Which of the following simple molecules is being removed during the reaction between
ethanol and acetic acid to form ethyl acetate?

A. H20
B. NH3
C. o2
D. HCI

27. Which one of the following compounds is a tertiary alkyl halide?

A. 1-chloropropane.
B. tribromomethane.
C. 2-methyl-2-bromopropane.
D. 3-iodopentane.

28. contains a C = C bond in its structure.

A. CH2CICH2CI
B. CH3CCCH3
C. CH3CH(CH3)CH3
D. CH3CH2CHCH2

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29. What is the product of oxidation of pentanal, CH3(CH2)3CHO?

A. Pentanoic acid
B. Hexanol
C. Pentanone
D. Pentene

30. Dehydration of an alcohol will produce a/an

A. alkyne
B. secondary alcohol
C. ketone
D. alkene

31. is the general formula for aldehydes.

A. CnH2n + 1COOH
B. CnH2n + 2O
C. Cnn2n + iCHO
D. CnH2n + 1OH

32. Which of the following hydrocarbons has the highest boiling point?

A. C7H16
B. C5H12
C. C4H10
D. C 3 H 6

33. Which of the following reactions represents a saponification reaction?

A. CH3COOH + NaOH —> CH3COONa + H 2 0

B. CH3COOH + C2H5OH —> CH3COOC2H5 + H 2 0
NaOH
C. CH3COOC2H5 > CH3COOH + C2H5OH
D. C6H5COOH + NaOH > C6H6 + Na 2 C0 3

34. Consider the following organic reaction: X + HCI —S*C3H7CI. X is most probably an

A. amine
B. alkane
C. aldehyde
D. alkene

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35. Which of the following processes are the correct names for the changes X and Y given
below?

X: Ethanol —> Ethene

Y: Ethene >. Ethane

A. X: elimination, Y: hydrogenation
6. X: substitution, Y: addition
C. X: hydrolysis, Y: combustion
D. X: dehydration, Y: decomposition

36. Which of the following compounds would react with ammonia to form an amine?

A. CH3CH2CH2CI
B. CH3CH2COCI
C. CH3CH2COOH
D. CH3CH2CH2OH

37. Consider the following reaction of propanoic acid with a reagent X in the presence of
concentrated H 2 S0 4 :
CH3CH2COOH + Reagent X —> CH3CH2COOCH3 + H 2 0

The reagent X is

A. sodium ethoxide
B. ethanol
C. methanal
D. methanol

38. The fourth member of the homologous series having the functional group — COOH is
called .

A. butanol
B. butanoicacid
C. pantanoic acid
D. propanone

39. The monomer unit for the addition polymer: —(CH2— CH — CH 2 — CH)— is
I I
CH 3 CH 3
A. CH 2 =CHCH 3
B. CH3CH2CH3
C. CH3CH(CH3)CH3
D. CH 3 CH=CHCH 3

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CONFIDENTIAL 10 HS/APR2009/ENV123

40. Which of the following reagents may be used to convert an alkyl halide to an alkene?

A. Alcoholic KOH.
B. Concentrated sulphuric acid.
C. Aqueous NaOH.
D. Cold dilute KMn0 4 .

41. Which of the following is FALSE about the compound bromoethane?

A. It belongs to the family of compounds called alkyl halides.

B. It is produced by dehydration of ethanol with HBr.
C. It is one of the products of substitution reaction of ethane with Br2.
D. It's common name is ethyl bromide.

42. A compound M on reacting with NaHC0 3 solution releases C0 2 . The test indicates M
contains the functional group:

A. - C - O H

B. - C s c -

C. OH
I
-c=o
D. NH2
I
-c = o

43. Which of the following compounds would most readily decolourise Br2 in CCI4?

A. CH3CH2CHCH2
B. Crl3CH2CH2CH3
C. CH3CH2CH2OH
D. C6H5COOH

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44. Which of the following structures represents the peptide linkage in a protein molecule?

A. - C - O -
II
O

B. - C H -
I
OH

C. - N H - C - O -

D. - C - N -
II I
O H

45. Which of the following pairs of functional groups is present in an amino acid molecule?

A. -NH2 and -COOH

B. -OH and -COOH
C. -OH and -NH2
D. - NH2 and - CHO

46. The number of aromatic isomers with the same molecular formula C7H7Br is

A. 3
B. 4
C. 5
D. 6

47. Which of the following statements is FALSE for organic compound methylamine?

A. Dissolves in water to form ammonium hydroxide.

B. Contains the functional group — NH2.
C. Reacts with acids to form salts.
D. Is a stronger base than NH3.

48. Which one of the following statements is FALSE for fatty acids?

A. Polyunsaturated fatty acids contain more than one — COOH groups.

B. Fatty acids are long-chain carboxylic acids.
C. Fatty acids can be produced by base-hydrolysis of triglycerides.
D. Animal fats usually have more saturated fatty acids than vegetable oils.

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49. Alkyl halides may be prepared from the following compounds EXCEPT

A. alkenes
B. alkanes
C. carboxylic acids
D. alcohols

50. The following statements are TRUE EXCEPT:

A. Carboxylic acids are weak acids.

B. Ethene is more reactive than ethane.
C. Dioxins are toxic aromatic hydrocarbons.
D. Methanol is more soluble in water than methane.

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PART B (50 marks)

Answer ALL questions.

QUESTION 1

a) Write the IUPAC names of the following compounds:

i) CH3CH2CH = CHCH2CHCH3
I
CH3
(1 mark)

ii) CH3CH2CHCH2OH
I
CH2
I
CH3
(1 mark)

iii)

(1 mark)

b) Give the name and molecular formula of

i) an alkane that has 8 carbon atoms,

ii) an alkene that has 7 carbon atoms.
(4 marks)

c) PCB and PAH are the acronyms for two types of organic compounds which can bring
about undesirable environmental and health problems.

i) What does "PCB" and "PAH" stand for?

ii) Give one example for each of these types of compounds.
(4 marks)

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QUESTION 2

Choose from the list of substances A — J, the substance or substances that best fits the
descriptions given below. Each substance may be chosen once, more than once, or none at
all.

A. CH3CH2COOH F. CH3COCH3
B. C3H6 G. CH3NH2
C. CH3CH(OH)CH3 H. CH2CHCI
D. CH3COOCH2CH3 I. C6H5CH3
E. CH3CH2CHO J. CH3CH(CH3)CH2OH

a) t gives a positive iodoform test,

b) t can be oxidised to give a ketone.

c) They are isomers.

d) It can be obtained by dehydration of propanol.

e) It reacts with HCI to form a salt.

f) It is an aromatic hydrocarbon.

g) Its molecule contains a tertiary (3°) carbon atom.

h) It undergoes hydrogenation reaction to produce a saturated hydrocarbon.

i) It is a secondary alcohol.

j) It has a sweet, pleasant smell.

k) It can be used as a monomer to produce the addition polymer called PVC.

I) They react to produce an ester.

m) It comes from the same homologous series as formaldehyde.

(15 marks)

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QUESTION 3

a) A liquid organic compound W decolourised warm, acidified potassium permanganate

solution. On distillation of the decolourised liquid mixture, a liquid distillate, X, was
obtained. X reacted with methanol, in the presence of concentrated sulphuric acid, to
form a sweet smelling product, Y.

i) Select, from the list given below, the possible identities of W, X and Y.

propene, ethanoic acid, propanone, ethanal, methyl propanoate, 1-propanol, propanoic

acid, propyl methanoate, butanone.

ii) Write equations for the conversion of W to X, and of X to Y.

(7 marks)

b) Draw the structural formulas and give the IUPAC names of all amines with the formula
C3H9N.
(4 marks)

QUESTION 4

a) Give a simple chemical test to distinguish cyclohexene from hexane.

(2 marks)

b) Write equations for the reactions between the following pairs of reactants.

i) 2-butanol and hydrogen bromide,

ii) 3-hexene and hydrogen chloride.
(4 marks)

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c) Choose from the list of reaction types P — X, the one that is most appropriate for the
changes given below. Each type of reaction may be chosen once only.

P: Elimination S: Substitution V: Addition

Q: Saponification T: Dedyd ration W: Reduction
R: Oxidation U: Hydrogenation X: Chlorination

i) CH3CH2CH2CHO -• CH3CH2CH2COOH
ii) C H 3 C H C H C H 3 + HBr -» CH3CH2CHBrCI-h
iii) CH4 + F2 -» CH3F + HF
iv) CH3CH(OH)CH 3 —*• CH3CHCH2 + H 2 0
v) C3H6 + H2 —* C3H8
vi) HCI
C3H7CI —> C3H6 •*•
vii) C6H5COOH -* C6H5OH
(7 marks)

END OF QUESTION PAPER

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