A Level Official Exam Material
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Unit 2: Energetics, Group Chemistry,
Halogenoalkanes and Alcohols
Halogenoalkanes and Alcohols
Topic 10: Organic Chemistry
For both SL and HL students
1. [1 mark]
Which homologous series has the general formula CnH2nO (n > 2)?
A. Alcohols
B. Carboxylic acids
C. Ethers
D. Ketones
2. [1 mark]
Which conditions best favour oxidation of primary alcohols directly to carboxylic acids?
A. Excess acidified potassium dichromate (VI) and distillation
B. Excess acidified potassium dichromate (VI) and reflux
C. Few drops of acidified potassium dichromate (VI) and distillation
D. Few drops of acidified potassium dichromate (VI) and reflux
3. [1 mark]
What are nucleophiles most likely to react with?
A. Alkenes
B. Benzene
C. Alkanes
D. Halogenoalkanes
6a. [3 marks]
An organic compound, A, reacts with ethanoic acid to produce B using concentrated sulfuric acid as a catalyst.
6b. [2 marks]
Explain, with reference to Le Châtelier’s principle, the effect of using dilute rather than concentrated sulfuric acid as the catalyst on the yield of the reaction.
6c. [2 marks]
Explain, with reference to intermolecular forces, why B is more volatile than A.
6d. [1 mark]
Compound A can also react with bromine. Describe the change observed if A is reacted with bromine.
8. [1 mark]
Which compounds are members of the same homologous series?
A. propanal, propanone, propanoic acid
B. propane, propene, propyne
C. hexan-1-ol, hexan-2-ol, hexan-3-ol
D. ethanol, propan-1-ol, butan-1-ol
9. [1 mark]
Which reagents and conditions are best for converting propan-1-ol into propanoic acid?
A. Reflux with acidified potassium dichromate (VI)
B. Reflux with aqueous sodium hydroxide
C. Distil with acidified potassium dichromate (VI)
D. Distil with aqueous sodium hydroxide
10. [1 mark]
What is produced when chlorobutane is treated with aqueous sodium hydroxide solution?
A. butane
B. butanoic acid
C. butanal
D. butan-1-ol
11. [1 mark]
Which combination best describes what is happening to chloromethane, CH3Cl, in the equation below?
CH3Cl (g) + H2 (g) ⇌ CH4 (g) + HCl (g)
A. Oxidation and addition
B. Oxidation and substitution
C. Reduction and addition
D. Reduction and substitution
12. [1 mark]
How many dichlorinated butane isomers can be formed by the halogenation of CH3CH2CH2CH3 with excess Cl2 in the presence of UV light?
A. 4
B. 6
C. 8
D. 10
13. [1 mark]
Which structure represents a repeating unit of a polymer formed from propene?
A. –CH2–CH(CH3)–
B. –CH2–CH2–CH2–
C. –CH(CH3)–CH(CH3)–
D. –CH2–CH2–
14. [1 mark]
Which is a homologous series?
A. C2H4, C3H5, C4H6
B. C2H2, C3H4, C4H6
C. C2H2, C2H4, C2H6
D. C2H2, C4H4, C6H6
15. [1 mark]
Which reaction mechanisms are typical for alcohols and halogenoalkanes?
16g. [1 mark]
Deduce what would be observed when Compound B is warmed with acidified aqueous potassium dichromate (VI).
16h. [1 mark]
Iodomethane is used to prepare CH3MgI. It can also be converted into methanol:
CH3I + HO– → CH3OH + I–
Identify the type of reaction.
16i. [2 marks]
Outline the requirements for a collision between reactants to yield products.
16j. [1 mark]
The polarity of the carbon–halogen bond, C–X, facilitates attack by HO–.
Outline, giving a reason, how the bond polarity changes going down group 17.
17a. [1 mark]
Carbon forms many compounds.
C60 and diamond are allotropes of carbon.
Outline one difference between the bonding of carbon atoms in C60 and diamond.
17b. [2 marks]
Explain why C60 and diamond sublime at different temperatures and pressures.
17c. [2 marks]
State two features showing that propane and butane are members of the same homologous series.
17d. [2 marks]
Describe a test and the expected result to indicate the presence of carbon–carbon double bonds.
17e. [1 mark]
But-2-ene reacts with hydrogen bromide.
Draw the full structural formula of but-2-ene.
17f. [1 mark]
Write the equation for the reaction between but-2-ene and hydrogen bromide.
17g. [1 mark]
State the type of reaction.
19. [1 mark]
Which pair of compounds are structural isomers?
A. Propane and propene
B. Propanal and propanone
C. Propan-1-ol and propanal
D. Propyl propanoate and propanoic acid
20. [1 mark]
What is the general formula of alkynes?
A. CnH2n+2
B. CnH2n
C. CnH2n−2
D. CnHn
21a. [1 mark]
1-chloropentane reacts with aqueous sodium hydroxide.
Identify the type of reaction.
21b. [1 mark]
Outline the role of the hydroxide ion in this reaction.
21c. [2 marks]
Suggest, with a reason, why 1-iodopentane reacts faster than 1-chloropentane under the same conditions. Use section 11 of the data booklet for consistency.
22b. [3 marks]
Formulate equations for the two propagation steps and one termination step in the formation of chloroethane from ethane.
23. [1 mark]
Which series is in order of increasing boiling point?
A. CH2CH2CH3OH CH3COCH3 CH3CH2CH3
B. CH3CH2CH3 CH3COCH3 CH2CH2CH3OH
C. CH3COCH3 CH2CH2CH3OH CH3CH2CH3
D. CH3CH2CH3 CH2CH2CH3OH CH3COCH3
24. [1 mark]
What is the name of this compound, applying IUPAC rules?
25. [1 mark]
What is formed in a propagation step of the substitution reaction between bromine and ethane?
A. CH3CH2•
B. CH3CH2CH2CH3
C. H•
D. Br−
26. [1 mark]
Which monomer would produce the polymer shown?
A. CF3CCl2F
B. CF3CClHF
C. CF2CClF
D. CF2CF2
27. [1 mark]
Which is in the same homologous series as CH3OCH3?
A. CH3COCH3
B. CH3COOCH3
C. CH3CH2CH2OH
D. CH3CH2CH2OCH3
28. [1 mark]
What is the IUPAC name of the molecule shown?
A. 2,4-dimethylhexane
B. 3,5-dimethylhexane
C. 2-methyl-4-ethylpentane
D. 2-ethyl-4-methylpentane
29. [1 mark]
Which monomer forms the polymer shown?
A. CH(Cl)=CH(CH3)
B. CH2=C(Cl)CH3
C. (CH3)2CHCl
D. CH2=CHCl
30. [1 mark]
Which is a propagation step in the free-radical substitution mechanism of ethane with chlorine?
A. Cl2 → 2 •Cl
B. •C2H5 + Cl2 → C2H5Cl + •Cl
C. •C2H5 + •Cl → C2H5Cl
D. C2H6 + •Cl → C2H5Cl + •H
31. [1 mark]
Which spectra would show the difference between propan-2-ol, CH3CH(OH)CH3, and propanal, CH3CH2CHO?
I. mass
II. infrared
III. 1H NMR
II. infrared
III. 1H NMR
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
32a. [1 mark]
Ethanol is obtained by the hydration of ethene, C2H4.
State the class of compound to which ethene belongs.
32b. [1 mark]
State the molecular formula of the next member of the homologous series to which ethene belongs.
32d. [1 mark]
Suggest two possible products of the incomplete combustion of ethene that would not be formed by complete combustion.
If you need the markscheme, including the examiners' reports for each question, and more exam and teaching materials on this topic, contact me through the contact page