Hydrocarbons 9

21 When heated with chlorine, the hydrocarbon 2,2-dimethylbutane undergoes free radical
substitution.

In a propagation step the free radical X• is formed.

CH3

CH3CH2 C CH3 + Cl ● → X● + HCl

CH3

How many different forms of X• are possible?

10 s10_11(21)
A 1 B 2 C 310 D 4
26 In many countries plastic waste is collected separately and sorted. Some of this is incinerated to
provide
26 In many heat for power
countries stations.
plastic waste is collected separately and sorted. Some of this is incinerated to
provide heat for power stations.
22 What will react differently with the two isomeric alcohols, (CH3)3CCH2OH and
Why3)is
(CH pvc, polyvinylchloride, removed from any waste that is to be incinerated?
2CHCH2CH2OH?
Why is pvc, polyvinylchloride, removed from any waste that is to be incinerated?
A acidified
A It destroys the ozone
aqueous layer. manganate(VII)
potassium
A It destroys the ozone layer.
B concentrated
B It does not burn easily.
sulfuric acid
B It does not burn easily.
C phosphorus
C It is easily biodegradable.
pentachloride
C It is easily biodegradable.
D sodium
D Its combustion products are harmful. s10_11(26)
D Its combustion products are harmful.

27 Which
23 Polymerisation of 1,1-dichloroethene
reagent will give similar results produces a dense, and
with both butanone high butanal?
melting point substance that does
not allow gases to pass through. It is used as cling wrapping.
27 Polymerisation of 1,1-dichloroethene produces a dense, high melting point substance that does
A allow
not acidified aqueous
gases to passpotassium
through. Itdichromate(VI)
is used as cling wrapping.
Which sequence appears in a short length of the polymer chain?
B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution)
Which sequence appears in a short length of the polymer chain?
A [ CH2CCl2CH2CCl2CH2CCl2 ]
C an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent)
A [ CH2CCl2CH2CCl2CH2CCl2 ]
B 2,4-dinitrophenylhydrazine
D [ CHClCHClCHClCHClCHClCHCl reagent ]
B [ CHClCHClCHClCHClCHClCHCl ]
C [ CCl2CCl2CCl2CCl2CCl2CCl2 ]
24 C
What[ CCl 2CCl2CCl 2CCl 2CCl2CCl2 is] refluxed with a solution of NaBH4? s10_11(27)
D [ CH2CCl2CHClCHClCH2CCl2 ]
is formed when propanone

D [ CH2CCl2CHClCHClCH2CCl2 ]
A propanal

28 B
Whenpropan-1-ol
an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form
an alcohol
28 When C4H9OH,
an isomer Y ofthemolecular
rate of reaction
formulais Cfound to be unaffected by changes in the concentration
4H9Br undergoes hydrolysis in aqueous alkali to form
C propan-2-ol
–
of OH ions present.
an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration
D OH –
propane
of ions present.
Which is the most likely molecular structure of Y?
Which is the most likely molecular structure of Y?
25 Which 3CH2CH2CHis
A CHcompound 2Bra product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium
hydroxide?
A
B CHCH3CH
CH2CH 2CH2Br
CHBrCH
3 2 3

B
A (CH33CH
CH
CH OH 2CHBrCH 3 C3H7CO 2− Na +
C 3 )2CHCH2Br B C3H7OH C C3H7CO2H D
C
D (CH33))23CHCH
(CH CBr 2Br
D (CH3)3CBr
29 Which isomer of C4H10O forms three alkenes on dehydration?
29 Which isomer of C4H10O forms three alkenes on dehydration?
A butan-1-ol
© UCLES 2010 9701/11/M/J/10 [Turn over
A
B butan-1-ol
butan-2-ol
The responsesA
The responses
responses AAto
totoD
DDshould
should
should bebe
be selected
selected
selected onon
on thethe
the basis
basis
basis of of
of
Introduction to organic chemistry 11
AA BB C C D D
A B C D
30 Which compound exhibits both cis-trans and optical isomerism?
1,
1,222and
and333 1 and 2 2 2 and 3 3 1 only1 only
1, and 11 and
and 2 2 and
2 and 3 1 only
are
A CH3CH=CHCH
are 2CH3 only are
only are only are
only is
are only are only areare is is
correct
correct correct
correct correct
correct correct
correct
B CHcorrect
CHBrCH=CH
3 2
correct correct correct
s10_11(30)
C CH
No other 3CBr=CBrCH
combination of statements
3 is used as a correct response.
No other
other combination
combinationofofstatements
statementsis is
used asas
used a correct response.
a correct response.
D CH3CH2CHBrCH=CHBr
38 Which structural formulae represent 2,2-dimethylpentane?
38
38 Which
Which structural
structuralformulae
formulaerepresent 2,2-dimethylpentane?
represent 2,2-dimethylpentane?
1 (CH3)2CHCH2CH(CH3)2
1 (CH33))22CHCH
1 (CH CHCH2CH(CH 3) 2
2CH(CH3)2
2 (CH3)3CCH2CH2CH3
2 s10_11(38)
(CH33))33CCH
2 (CH CCH2CH 2CH3
2CH2CH3
3 CH3CH2CH2C(CH3)3
3 CH3CH2CH2C(CH3)3
3 CH3CH2CH2C(CH3)3
39 Which reactions are examples of nucleophilic substitution?
39 Which reactions are examples of nucleophilic substitution?
39 Which reactions are examples of nucleophilic substitution?
1 CH3CH2Br + OH–– → CH3CH2OH + Br––
1 CH3CH2Br + OH –→ CH3CH2OH + Br –
1 CH3CH2Br + OH H ++ → CH3CH2OH + Br
2 CH3I + H2O ⎯⎯⎯ H → CH3OH + HI
2 CH3I + H2O ⎯⎯⎯ H→ + CH3OH + HI s10_11(39)
3 CH3CH2CH2Cl + NH3 →CH
2 CH 3 I + H 2 O ⎯⎯⎯ → CH3OH + HI
3CH2CH2NH2 + HCl
3 CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl
3 CH3CH2CH2Cl + NH3 → CH3CH2CH2NH2 + HCl
40 The diagram shows some laboratory apparatus.
40 The diagram shows some laboratory apparatus.
40 The diagram shows some laboratory apparatus.

water
water

heat water
heat
Which preparations could this apparatus be used for?
heat
Which preparations could this apparatus be used for?
1 bromoethane, from ethanol, sodium bromide and concentrated sulfuric acid
1 bromoethane, from ethanol, sodium bromide andfor?
concentrated sulfuric acid
2Which preparations
ethanal, could
from ethanol, this apparatus
sodium be used
dichromate(VI) and sulfuric acid
2 ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid
31 1,2-dibromoethane,
bromoethane, fromfromethanol, sodium
bromine s10_11(40)
bromide and concentrated sulfuric acid
and ethene
3 1,2-dibromoethane, from bromine and ethene
2 ethanal, from ethanol, sodium dichromate(VI) and sulfuric acid
3 1,2-dibromoethane, from bromine and ethene
© UCLES 2010 9701/11/M/J/10

© UCLES 2010 9701/11/M/J/10

© UCLES 2010 9701/11/M/J/10 [Turn over

© UCLES 2010 9701/11/M/J/10
 C
D 1
[ CCl2CCl2CCl2CCl2CCl2CCl2 ]
2,4-dinitrophenylhydrazine
A
Alcohol, carboxylic acid 2 itsreagent
B and C 3
derivatives D 4
D [ CH2CCl2CHClCHClCH2CCl2 ]
24 What is will
22 formed when differently
react propanone iswith
refluxed
the with
twoa solution of NaBH
isomeric 4?
alcohols, (CH3)3CCH2OH and
(CH3)2CHCH2CH2OH?
28 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form
A propanal
an alcohol
A acidified C4H 9OH, the rate of reaction is found to be unaffected by changes in the concentration
aqueous potassium manganate(VII)
–
of
B OH ions present.
propan-1-ol
B concentrated sulfuric acid
C propan-2-ol
Which is the most likely molecular structure of Y?
C phosphorus pentachloride
D CH
A propane
3CH2CH2CH2Br
s10_11(22)
D sodium
B CH3CH2CHBrCH3
25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium
C (CH3)2CHCH2Br
hydroxide?
23 Which reagent will give similar results with both butanone and butanal?
D (CH3)3CBr
A
A acidified
CH3OH aqueous B potassium
C3H7OH dichromate(VI)
C C3H7CO2H D C3H7CO 2− Na +
s10_11(25)
B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution)
29 Which isomer of C4H10O forms three alkenes on dehydration?
C an aqueous solution containing [Ag(NH3)2]+ (Tollens’ reagent)
A butan-1-ol
D 2,4-dinitrophenylhydrazine reagent
B butan-2-ol
C 2010
© UCLES 2-methylpropan-1-ol 9701/11/M/J/10 [Turn over
24 What is formed when propanone is refluxed with a solution of NaBH4? s10_11(29)
D 2-methylpropan-2-ol
A propanal
B propan-1-ol
C propan-2-ol
D propane

25 Which compound is a product of the hydrolysis of CH3CO2C3H7 by boiling aqueous sodium

© UCLES 2010 9701/11/M/J/10
hydroxide?

A CH3OH B C3H7OH C C3H7CO2H D C3H7CO 2− Na +

© UCLES 2010 9701/11/M/J/10 [Turn over

 D [ CH2CCl2CHClCHClCH2CCl2 ]
Halogenoalkane

28 When an isomer Y of molecular formula C4H9Br undergoes hydrolysis in aqueous alkali to form
an alcohol C4H9OH, the rate of reaction is found to be unaffected by changes in the concentration
of OH– ions present.

Which is the most likely molecular structure of Y?

A CH3CH2CH2CH2Br
B CH3CH2CHBrCH3
C (CH3)2CHCH2Br s10_11(28)
D (CH3)3CBr

29 Which isomer of C4H10O forms three alkenes on dehydration?

A butan-1-ol
B butan-2-ol
C 2-methylpropan-1-ol
D 2-methylpropan-2-ol

© UCLES 2010 9701/11/M/J/10

 C phosphorus pentachloride
D sodium
D sodium
Carbonyl compounds
23 Which reagent will give similar results with both butanone and butanal?
23 Which reagent will give similar results with both butanone and butanal?
A acidified aqueous potassium dichromate(VI)
A acidified aqueous potassium dichromate(VI)
B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution)
B an alkaline solution containing complexed Cu2+ ions (Fehling’s solution)
C an aqueous solution containing [Ag(NH ) ]+ (Tollens’ reagent)
C an aqueous solution containing [Ag(NH33)22]+ (Tollens’ reagent)
D 2,4-dinitrophenylhydrazine reagent
D 2,4-dinitrophenylhydrazine reagent

24 What is formed when propanone is refluxed with a solution of NaBH ?

24 What is formed when propanone is refluxed with a solution of NaBH44?
A propanal
A propanal
B propan-1-ol
B propan-1-ol
C propan-2-ol
C propan-2-ol
D propane
D propane

25 Which compound is a product of the hydrolysis of CH CO C H by boiling aqueous sodium

25 Which compound is a product of the hydrolysis of CH33CO22C33H77 by boiling aqueous sodium
hydroxide?
hydroxide?
A CH OH B C H OH C C H CO H D C H CO − Na +
A CH33OH B C33H77OH C C33H77CO22H D C33H77CO 2−2 Na +

© UCLES 2010 9701/11/M/J/10 [Turn over

© UCLES 2010 9701/11/M/J/10 [Turn over