Topics 10 and 20.1-20.5 Organic Chemistry
HL Test 2013
Multiple Choice: Place your answers on the answer sheet provided.
1.
2.
Which of the following are isomers of hexane?
I.
2-methylhexane
II.
2,2-dimethylbutane
III.
2-methylpentane
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
Which conditions are required to obtain a good yield of a carboxylic acid when ethanol is oxidized using
potassium dichromate(VI), K2Cr2O7(aq)?
3.
I.
Add sulfuric acid
II.
Heat the reaction mixture under reflux
III.
Distil the product as the oxidizing agent is added
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
When bromine water is shaken with a liquid organic compound, it is rapidly decolorized. What can be
determined from this test?
4.
A.
The compound is an alcohol.
B.
The compound is an alkane.
C.
The compound is an alkene.
D.
The compound is an iodoalkane.
What is the IUPAC name for CH3CH2CH(CH3)CH3?
A.
1,1-dimethylpropane
B.
2-ethylpropane
C.
2-methylbutane
D.
3-methylbutane
5.
Propane, C3H8, undergoes incomplete combustion in a limited amount of air. Which products are most
likely to be formed during this reaction?
6.
A.
Carbon monoxide and water
B.
Carbon monoxide and hydrogen
C.
Carbon dioxide and hydrogen
D.
Carbon dioxide and water
Which products can be potentially obtained from crude oil and are economically important?
I.
7.
8.
Plastics
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
II.
Margarine
III.
Motor fuel
Which compound forms when hydrogen bromide is added to but-2-ene?
A.
2-bromobutane
B.
2,3-dibromobutane
C.
1-bromobutane
D.
1,2-dibromobutane
Propene is converted to propanone in a two stage process.
Propene → X → Propanone
What is the formula of compound X?
9.
10.
A.
CH3CHBrCH3
B.
CH3CH2CH2Br
C.
CH3CHOHCH3
D.
CH3CH2CH2OH
What structural feature must a molecule have in order to undergo addition polymerization?
A.
Two functional groups
B.
A carbon–carbon double bond
C.
Carbon atoms singly bonded together
D.
A polar covalent bond
Which is a tertiary halogenoalkane?
A.
CH3CH2CH2Br
B.
CH3CH2CH(CH3)Cl
C.
C(CH3)3Br
D.
CH3CHClCH2CH3
11.
12.
13.
What are some uses of esters?
I.
Flavouring agents
II.
Perfumes
III.
Solvents
A.
I and II only
B.
I and III only
C.
II and III only
D.
I, II and III
Which order is correct when the following substances are arranged in order of increasing boiling point?
A.
C2H4 < CH3CHO < CH3CH2OH
B.
CH3CHO < CH3CH2OH < C2H4
C.
CH3CH2OH < C2H4 < CH3CHO
D.
C2H4 < CH3CH2OH < CH3CHO
What organic product is formed in the following reaction occurring at 300 °C in acidified conditions?
(CH3CH2)CH=CH(CH2CH3) + H2O (g)
14.
A.
CH3(CH2)2CH(OH)CH2CH3
B.
CH3(CH2)5CH3
C.
CH3(CH2)2CH(OSO3H)CH2CH3
D.
CH3(CH2)6OH
What is the structural formula of 2,3-dibromo-3-methylhexane?
A.
CH3CHBrCHBrCH(CH3)CH2CH3
B.
CH3CHBrCBr(CH3)CH2CH2CH3
C.
CH3CH2CHBrCBr(CH2CH3)2
D.
CH3CHBrCHBrCH(CH2CH3)2
15.
The compounds H2NCH2CH2NH2 and HOOCCH2COOH react to form a polymer. What is the structure
of the repeating unit of the polymer?
16.
A.
( HNCH2CONHCH2CH2NHCO )
B.
( HNCH2CH2NHCOCH2CO )
C.
( OCCH2CONHCH2NHCO )
D.
( HNCH2CH2NHCOCH2NH )
Which type of reaction occurs when 2-iodo-2-methylpropane, C(CH3)3I, reacts with aqueous sodium
hydroxide, NaOH(aq)?
17.
A.
Addition
B.
Free-radical substitution
C.
SN1
D.
SN2
Propanitrile can be prepared by reacting bromoethane with potassium cyanide. Which statement is not
correct about the reaction between bromoethane and potassium cyanide?
18.
A.
The reaction is bi-molecular.
B.
The reaction follows the SN2 mechanism.
C.
Homolytic fission occurs between the carbon-bromine bond in bromoethane.
D.
The cyanide ion, :CN–, acts as a nucleophile.
What is the main organic product formed from the reaction of CH3CH2OH with CH3CH2CH2COOH in
the presence of an acid catalyst?
19.
A.
Ethyl butanoate
B.
Butyl ethanoate
C.
Ethyl propanoate
D.
Propyl ethanoate
What is the product of the following reaction?
CH3CH2CH2CN + 2H2
20.
A.
CH3CH2CH2NH2
B.
CH3CH2CH2CH2NH2
C.
CH3CH2NH2
D.
CH3CH2CH2CH3
Which process can produce a polyester?
A.
Addition polymerization of a dicarboxylic acid
B.
Condensation polymerization of a diol and a dicarboxylic acid
C.
Addition polymerization of a diol and dicarboxylic acid
D.
Condensation polymerization of a dicarboxylic acid
Organics HL Test- Part 2 Free Response
1.
(i)
/42
Name:______________________
Draw four structural isomers of molecular formula C4H10O which contain the –OH
group.
(4)
(ii)
On reaction with acidified potassium dichromate(VII), two of the isomers are oxidized in two
steps to produce different products. Draw the structural formula of the two products formed from
one of the isomers.
(2)
(iii)
A third isomer is oxidized in one step. Draw the structural formula of the organic product formed.
(1)
(iv)
State the colour change that takes place in these oxidation reactions.
(1)
(v)
Identify the isomer which resists oxidation by acidified potassium dichromate(VI).
(1)
2.
3.
Halogenoalkanes can also undergo substitution reactions with potassium hydroxide solution.
(i)
State an equation for the reaction of C4H9Cl with KOH.
......................................................................................................................................
......................................................................................................................................(1)
(ii)
Substitution reactions may occur by either of two mechanisms namely SN1 or SN2.
Outline the
meaning of the term SN1.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
...................................................................................................................................... (2)
(iii) Predict the mechanism (SN1 or SN2) expected for the reaction of the following halogenoalkanes
with aqueous KOH.
1-chlorobutane to form butan-1-ol: ............................................................................
4.
2-chloro-2-methylpropane to form 2 methylpropan-2-ol: ..............................................
(ii)
State the type of polymerization reaction shown by but-2-ene.
(2)
......................................................................................................................................
......................................................................................................................................
(1)
(iii) Deduce the structure of the resulting polymer from (ii) showing three repeating units.
(1)
(iv)
Explain why monomers are often gases or volatile liquids, but polymers are solids.
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
......................................................................................................................................
(2)
6.
Two compounds, A and D, each have the formula C4H9Cl.
Compound A is reacted with dilute aqueous sodium hydroxide to produce compound B with a formula
of C4H10O. Compound B is then oxidized with acidified potassium manganate(VII) to produce
compound C with a formula of C4H8O. Compound C resists further oxidation by acidified potassium
manganate(VII).
Compound D is reacted with dilute aqueous sodium hydroxide to produce compound E with a formula
of C4H10O. Compound E does not react with acidified potassium manganate(VII).
Deduce the structural formulas for compounds A, B, C, D and E.
A:
B:
C:
D:
E:
(Total 5 marks)