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AQA_A level_Chem_1_Practice ch13.indd

The document contains practice questions related to organic chemistry, specifically focusing on reactions involving halogenoalkanes, nucleophiles, and free radical mechanisms. It includes detailed mechanisms for various reactions, product formation, and the environmental impact of certain compounds like tetrachloromethane. Additionally, it discusses the properties of nucleophiles and the conditions required for different types of reactions.

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Mahebul Mazid
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16 views3 pages

AQA_A level_Chem_1_Practice ch13.indd

The document contains practice questions related to organic chemistry, specifically focusing on reactions involving halogenoalkanes, nucleophiles, and free radical mechanisms. It includes detailed mechanisms for various reactions, product formation, and the environmental impact of certain compounds like tetrachloromethane. Additionally, it discusses the properties of nucleophiles and the conditions required for different types of reactions.

Uploaded by

Mahebul Mazid
Copyright
© © All Rights Reserved
We take content rights seriously. If you suspect this is your content, claim it here.
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Download as PDF, TXT or read online on Scribd
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●● Practice questions

Practice questions
1 a) ultraviolet light (1)
b) hydrogen chloride (1)
c) Initiation: Cl2 → Cl● + Cl●
Propagation: Cl● + CH4 → ●CH3 + HCl
●CH
3 + Cl2 → Cl● + CH3Cl
Termination: Cl● + ●CH3 → CH3Cl
●CH
3 +●CH3 → CH3CH3 (4)
d) free radical substitution reaction (1)
2 a) A nucleophile is an electron pair donor. (1)
b) i) CH3CH2Br + KOH → CH3CH2OH + KBr (1)
ii) CH3CH2Br + KCN → CH3CH2CN + KBr (1)
c)
H H (1)

H C C C N
H H
d) Reacting a halogenoalkane with an aqueous solution of potassium
cyanide produces an organic product which has one more carbon
in the chain. This nitrile can be easily converted to other functional
groups. (1)
3
Product Reagent Conditions Starting halogenoalkane

pent-2-ene KOH Dissolve reactants and reagents in ethanol 2-bromopentane(2)

propanenitrile KCN Dissolve reagent in water; dissolve halogenoalkane in a bromoethane(2)


minimum volume of ethanol; reflux gently
propan-2-ol NaOH Dissolve reagent in water; dissolve halogenoalkane in a 2-bromopropane(2)
minimum volume of ethanol; reflux gently
methylamine ammonia Reagent in excess; in a sealed tube under pressure bromomethane(2)

diethylamine ammonia Reagent and halogenoalkane in 1:1 ratio or halogenoalkane bromoethane(2)


in excess in a sealed tube under pressure 1

4 a) Br2 → Br● + Br●


Br● + C2H6 → ●CH2CH3 + HBr
●CH CH
2 3 + Br2 → Br● + CH2BrCH3
●CH CH
2 3 + Br● → CH2BrCH3 (4)
b) 1,1-dibromoethane and 1,2-dibromoethane (2)
c) ●CH CH
2 3 + ●CH2CH3 → CH3CH2CH2CH3 (1)
1
5 2 2 Cl2 + C3H8 → CHCl2CHClCHCl2 (3)
6 a) propan-1-ol propene (4)
H H
H H H
H C
H C C C O H C C H
H H H H H
b) Propan-1-ol is formed by a nucleophilic substitution mechanism
which is more probable when the potassium hydroxide is dissolved
in water and the halogenoalkane is dissolved in a minimum volume
of ethanol and the mixture refluxed gently. The alkene is formed by
an elimination reaction and is more probable when the reagent and
halogenoalkane are dissolved in ethanol and no water is present. (2)
7 a) i) Cl2 → ●Cl + ●Cl (1)
ii) CHCl3 + ●Cl → ●CCl3 + HCl
●CCl
3 + Cl2 → CCl4 (1)
iii) ●CCl3 + ●Cl → CCl4 (1)
b) Did you realise that this overall reaction was not for the reaction
you wrote the mechanism for in part a?
CH2Cl2 + 2Cl2 → CCl4 + 2HCl (1)
c) i) Tetrachloromethane is inert in the atmosphere at the surface
of the earth but it escapes into the stratosphere where it forms
chlorine free radicals. The chlorine free radicals react with
the ozone in the stratosphere in a free radical chain reaction
decomposing the ozone into oxygen. The ozone in the
13 HALOGENOALKANES

stratosphere is essential as it absorbs wavelengths of ultraviolet


radiation from the sun that other gases do not absorb. These
wavelengths can cause skin cancer and damage plant tissue and
reduce plankton population in the oceans.
One chlorine free radical can decompose 100,000 molecules of
ozone.
●Cl + O3 → ClO● + O2
ClO● + O3 → ●Cl + 2O2
Overall

2 2O3 → 3O2 (3)


ii) Tetrachloromethane can also be used as a refrigerant or a fire
extinguisher. (2)
d) i) F H (1)

F C C H
F F
ii) Hydrofluorocarbons are also non-toxic with similar chemical
and physical properties to CFC’s but they do not harm the

Practice questions
ozone layer to the same extent as the compounds they replace.
(They do however contribute to another environmental problem,
Global Warming. Therefore the search goes on to find yet more
suitable refrigerants, solvents.) (1)
8 a) A nucleophile is an electron pair donor. (1)
b) Compound 1: propanenitrile (1)
Compound 2: ethanol (1)
Compound 3: ethylamine (1)
c) i) cyanide ions ( the reagent is potassium cyanide) (1)
ii) ammonia (1)
d) i) H H H H (2)
–
H C Cδ+ Brδ– H C C O H + Br
H H H H
–
OH
ii) H H H H (2)

H C Cδ+ Brδ– H C C C N + Br–


H H H H
–
CH
e) Reagent: sodium hydroxide
Reaction conditions: dissolve the sodium hydroxide in water and
dissolve the bromoethane in a minimum volume of ethanol and
reflux gently. (1)
f) Compound 3 is a primary amine. A primary amine is favoured by an
excess of ammonia in an attempt to prevent the formation of further
substituted amines as the amines formed are also nucleophiles and
will react with the bromoethane. If the ammonia is in excess there is
a greater probability of the ammonia reacting with the bromoethane
rather than the substituted amines. (1)
g) i) Reagent: potassium hydroxide (1)
Reaction conditions: dissolve both reagent and bromoethane 3
in ethanol, no water present (1)
ii) elimination (1)
9 B
10 D

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