1. Which molecule has a chiral centre?
A. CH3CH=CHCHO
B. (CH3)2C=CHCH2OH
C. CH3OCH2CH3
D. CH3CHOHCH2CH3
(Total 1 mark)
2. Which two molecules are cis-trans isomers of each other?
A. X and Z
B. X and Y
C. W and Y
D. W and Z
(Total 1 mark)
IB Questionbank Chemistry 1
3. What is the correct order of reaction types in the following sequence?
I II III
C3H7Br C3H7OH C2H5COOH C2H5COOC2H5
I II III
A. substitution oxidation condensation
B. addition substitution condensation
C. oxidation substitution condensation
D. substitution oxidation substitution
(Total 1 mark)
4. 2-chloro-3-methylbutane reacts with sodium hydroxide via an S N2 mechanism.
Explain the mechanism by using curly arrows to represent the movement of electron pairs.
(Total 4 marks)
IB Questionbank Chemistry 2
5. 1-chlorobutane can be converted to a pentylamine via a two stage process.
Deduce equations for each step of this conversion including any catalyst required and name the
organic product produced at each stage.
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(Total 5 marks)
6. Propanitrile can be prepared by reacting bromoethane with potassium cyanide. Which statement
is not correct about the reaction between bromoethane and potassium cyanide?
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.
(Total 1 mark)
IB Questionbank Chemistry 3
7. Which reactants could be used to form the compound below?
A. Butanoic acid and ethanol
B. Propanoic acid and ethanol
C. Ethanoic acid and propan-1-ol
D. Ethanoic acid and butan-1-ol
(Total 1 mark)
8. There are several structural isomers with the molecular formula C 5H11Br.
(a) Deduce the name of one of the isomers which can exist as enantiomers and draw three-
dimensional representations of its two enantiomers.
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(3)
IB Questionbank Chemistry 4
(b) All the isomers react when warmed with a dilute aqueous solution of sodium hydroxide
according to the equation below.
C5H11Br + NaOH → C5H11OH + NaBr
(i) The reaction with 1-bromopentane proceeds by an SN2 mechanism. Describe this
mechanism using structural formulas and curly arrows to represent the movement
of electron pairs.
(3)
(ii) The reaction with 2-bromo-2-methylbutane proceeds by an SN1 mechanism.
Describe this mechanism using structural formulas and curly arrows to represent
the movement of electron pairs.
(3)
IB Questionbank Chemistry 5
(iii) Explain why 1-bromopentane reacts by an SN2 mechanism whereas 2-bromo-2-
methylbutane reacts by an SN1 mechanism.
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(3)
(iv) Explain whether the boiling point of 1-bromopentane will be higher, lower or the
same as that of 2-bromo-2-methylbutane.
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(3)
(v) The product C5H11OH formed from the reaction with 1-bromopentane is warmed
with ethanoic acid in the presence of a few drops of concentrated sulfuric acid.
State the name of the type of reaction taking place and the structural formula of the
organic product.
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(2)
IB Questionbank Chemistry 6
(c) If the conditions of the reaction in (b) are changed so that a hot solution of sodium
hydroxide in ethanol is used then a different reaction occurs. The reaction with 2-bromo-
2-methylbutane gives two different organic products. State the type of reaction taking
place and suggest the identity (name or structure) of these two products.
Explain whether or not they can exist as geometrical isomers.
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(4)
(Total 21 marks)
9. What is the IUPAC name of CH3CH2CONH2?
A. Aminopropanal
B. Ethanamide
C. Propylamine
D. Propanamide
(Total 1 mark)
IB Questionbank Chemistry 7
10. What is the main organic product formed from the reaction of CH 3CH2OH with
CH3CH2CH2COOH in the presence of an acid catalyst?
A. Ethyl butanoate
B. Butyl ethanoate
C. Ethyl propanoate
D. Propyl ethanoate
(Total 1 mark)
11. How many isomers can exist for a compound with the molecular formula C 2H2Cl2?
A. 1
B. 2
C. 3
D. 4
(Total 1 mark)
IB Questionbank Chemistry 8
12. (a) Below are four structural isomers with molecular formula C4H9Br. State the
name of each of the isomers A, B, C and D.
(4)
(b) (i) Identify the isomer(s) which will react with aqueous sodium
hydroxide almost exclusively by an SN1 mechanism. State the meaning of the
symbols in the term SN1 mechanism.
(2)
(ii) Using the formula RBr to represent a bromoalkane, state an equation for the rate
determining step of this SN1 reaction.
(1)
(iii) Identify one isomer that will react with aqueous sodium hydroxide almost
exclusively by an SN2 mechanism. Draw the mechanism for this reaction using
curly arrows to represent the movement of electron pairs. Include the structural
formulas of the transition state and the organic product.
(4)
IB Questionbank Chemistry 9
(c) State and explain how the rates of the reactions in parts (b) (i) and (b) (iii) are affected
when the concentration of the sodium hydroxide is doubled.
(2)
(d) State and explain how the rate of reaction of 1-bromobutane with sodium hydroxide
compares with that of 1-chlorobutane with sodium hydroxide.
(2)
(e) Identify the isomer of C4H9Br that can exist as stereoisomers. Outline how a polarimeter
will distinguish between the isomers, and how their physical and chemical properties
compare.
(5)
(f) (i) State the type of reaction that occurs when isomer B,
CH3CHBrCH2CH3, reacts with a hot alcoholic solution of sodium hydroxide.
(1)
(ii) Explain how the reaction in part (f) (i) occurs by drawing the mechanism, using
curly arrows to represent the movement of electron pairs and identify the two
possible organic products.
(4)
(Total 25 marks)
13. What is the IUPAC name for the following compound?
CH3(CH2)2COOCH3
A. Methyl butanoate
B. Butyl ethanoate
C. Butyl methanoate
D. Methyl propanoate
(Total 1 mark)
IB Questionbank Chemistry 10
14. How many chiral carbon atoms are present in a molecule of 2,3-dibromobutane?
A. 1
B. 2
C. 3
D. 4
(Total 1 mark)
15. Existence of isomers leads to diversity of organic compounds.
(a) Describe what is meant by the term stereoisomers.
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(2)
(b) 1,3-dichlorocyclobutane exists as geometrical isomers, a form of stereoisomers.
(i) Draw and name the two geometrical isomers of 1,3-dichlorocyclobutane.
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(2)
IB Questionbank Chemistry 11
(ii) Identify the isomer with the higher boiling point and explain your reasoning.
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(3)
(Total 7 marks)
16. Which statement about stereoisomers is correct?
A. 1,2-dichloroethane has two geometrical isomers.
B. 1,2-dichloroethane has two optical isomers.
C. 1,2-dichloroethene has two geometrical isomers.
D. 1,2-dichloroethene has two optical isomers.
(Total 1 mark)
17. Identify the functional group present in HCOCH2CH3.
A. Ester
B. Ketone
C. Aldehyde
D. Alcohol
(Total 1 mark)
IB Questionbank Chemistry 12
18. What is the IUPAC name for HCOOCH2CH2CH3?
A. Butanoic acid
B. Butanal
C. Methyl propanoate
D. Propyl methanoate
(Total 1 mark)
19. Which statements about substitution reactions are correct?
I. The reaction between sodium hydroxide and 1-chloropentane predominantly
follows an SN2 mechanism.
II. The reaction between sodium hydroxide and 2-chloro-2-methylbutane
predominantly follows an SN2 mechanism.
III. The reaction of sodium hydroxide with 1-chloropentane occurs at a slower rate
than with 1-bromopentane.
A. I and II only
B. I and III only
C. II and III only
D. I, II and III
(Total 1 mark)
20. Which compound can exist as stereoisomers?
A. CH3CH2CHO
B. CH3CH2COCH3
C. CH3CH(CH3)2
D. CH3CH2CHOHCH3
(Total 1 mark)
IB Questionbank Chemistry 13
21. What is the IUPAC name of the compound CH3CH2COOCH2CH3?
A. Ethyl ethanoate
B. Propyl ethanoate
C. Ethyl propanoate
D. Pentyl propanoate
(Total 1 mark)
22. Deduce a two-step synthesis for each of the following conversions. For each step, state the
structural formulas of all reactants and products and state the conditions used in the reactions.
(i) Ethanol to ethyl ethanoate.
(2)
(ii) Propene to propanone.
(2)
(Total 4 marks)
23. (i) Describe geometrical isomerism.
(1)
(ii) Draw the geometrical isomers of but-2-ene.
(2)
(iii) Draw the two enantiomers of butan-2-ol.
(2)
(Total 5 marks)
IB Questionbank Chemistry 14
24. Which reaction occurs via a free-radical mechanism?
A. C2H6 + Br2 → C2H5Br + HBr
B. C2H4 + Br2 → C2H4Br2
– –
C. C4H9I + OH → C4H9OH + I
D. (CH3)3CI + H2O → (CH3)3COH + HI
(Total 1 mark)
25. Which compound could rotate the plane of polarization of polarized light?
A. (CH3)2CHCH2Cl
B. CH3CH2CH2CH2Cl
C. CH3CH2CHClCH3
D. (CH3)3CCl
(Total 1 mark)
26. What is the name of the ester formed when CH3CH2COOH and CH3OH react together?
A. Ethyl methanoate
B. Methyl ethanoate
C. Propyl methanoate
D. Methyl propanoate
(Total 1 mark)
27. The compound C4H7Cl can exhibit stereoisomerism.
(i) Draw the structural formulas of the two geometrical isomers of 1-chloro-but-2-ene.
(2)
IB Questionbank Chemistry 15
(ii) Explain why 1-chloro-but-2-ene shows geometrical isomerism.
(1)
(iii) Draw the structural formula of one isomer of C4H7Cl that shows optical isomerism and
identify the chiral carbon atom with an asterisk (*).
(2)
(Total 5 marks)
28. The compound but-2-ene-1,4-dioic acid forms two geometrical isomers which have different
physical and chemical properties.
(i) Explain the difference in the melting points of the two isomers.
(3)
(ii) Outline how the two isomers behave differently when gently heated.
(1)
(Total 4 marks)
29. What is the correct IUPAC name for the following compound?
CH 3 CHCH 2 CH 2 CN
CH 3
A. 4-methylbutanenitrile
B. 4-methylpentanenitrile
C. 2-methylbutanenitrile
D. 2-methylpentanenitrile
(Total 1 mark)
IB Questionbank Chemistry 16
30. What is the organic product of the reaction between ethanol and ethanoic acid in the presence of
sulfuric acid?
A. CH3CHO
B. CH3COOCH3
C. CH3CH2COOCH3
D. CH3COOCH2CH3
(Total 1 mark)
31. Which compound can exist as optical isomers?
A. H2NCH2COOH
B. H3CCONH2
C. H3CCHBrI
D. HCOOCH3
(Total 1 mark)
32. The molecular formula, C3H4Cl2 represents several isomeric compounds. Some isomers are
cyclic and some are unsaturated.
(a) Draw the structures of two cyclic compounds that are structural isomers and state the
names of both isomers.
(2)
IB Questionbank Chemistry 17
(b) Two of the non-cyclic compounds have geometrical isomers. Draw the structures of these
compounds and their geometrical isomers.
(2)
(Total 4 marks)
33. The compound, 2-bromobutane, CH3CHBrCH2CH3, can react with sodium hydroxide to form
compounds F, G and H.
Compound F, C4H10O, exists as a pair of optical isomers. Compounds G and H, C4H8, are
structural isomers, and compound H exists as a pair of geometrical isomers.
(i) Draw the structures of the two optical isomers of F.
(2)
(ii) Outline the use of a polarimeter in distinguishing between the optical isomers.
(2)
(iii) Draw diagrams to show the shapes of the two geometrical isomers of H.
(2)
(iv) Draw the mechanism, using curly arrows to represent the movement of electron pairs, to
show the formation of G.
(3)
(Total 9 marks)
34. A compound, J, has the molecular formula C2H4O2 and is obtained from a reaction between
methanoic acid and methanol. Write an equation for this reaction and state the name of
compound J.
(Total 3 marks)
IB Questionbank Chemistry 18
