1. What is the IUPAC name of CH3CH2CONH2?

A. Aminopropanal

B. Ethanamide

C. Propylamine

D. Propanamide
(Total 1 mark)

2. 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)

3. Identify the functional group present in HCOCH2CH3.

A. Ester

B. Ketone

C. Aldehyde

D. Alcohol
(Total 1 mark)

IB Questionbank Chemistry 1
4. What is the IUPAC name for HCOOCH2CH2CH3?

A. Butanoic acid

B. Butanal

C. Methyl propanoate

D. Propyl methanoate
(Total 1 mark)

5. What is the IUPAC name of the compound CH3CH2COOCH2CH3?

A. Ethyl ethanoate

B. Propyl ethanoate

C. Ethyl propanoate

D. Pentyl propanoate
(Total 1 mark)

6. What is the correct IUPAC name for the following compound?

CH 3CHCH 2CH 2CN

CH 3

A. 4-methylbutanenitrile

B. 4-methylpentanenitrile

C. 2-methylbutanenitrile

D. 2-methylpentanenitrile
(Total 1 mark)

IB Questionbank Chemistry 2
7. 2-chloro-3-methylbutane reacts with sodium hydroxide via an SN2 mechanism.
Explain the mechanism by using curly arrows to represent the movement of electron
pairs.

(Total 4 marks)

8. (a) Below are four structural isomers with molecular formula C4H9Br. State the
name of each of the isomers A, B, C and D.

(4)

IB Questionbank Chemistry 3
IB Questionbank Chemistry 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)

(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)

IB Questionbank Chemistry 5
9. The reaction between bromoethane, CH3CH2Br, and potassium cyanide is an example of
a nucleophilic substitution reaction.

(i) State whether this reaction is SN1 or SN2.

(1)

(ii) Explain the mechanism of the reaction using curly arrows to represent the
movement of electron pairs.
(4)

(iii) The organic product obtained in part (ii) can be reduced to form an amine.
State an equation for the reaction, naming the catalyst involved.
(2)
(Total 7 marks)

10. Bromoethane reacts with potassium hydroxide to undergo mainly a substitution

reaction or an elimination reaction depending on the reaction conditions used.

(i) State an equation and the reaction conditions used to control the products
formed in each case.
(4)

(ii) Explain the mechanism of the elimination reaction using curly arrows to
represent the movement of electron pairs.
(4)

(iii) Under certain conditions, the major product obtained in the elimination
reaction can undergo polymerization. Identify the type of polymerization this
major product undergoes.
(1)
(Total 9 marks)

11. (i) Describe the elimination of HBr from bromoethane. Your answer should
include the reagents, conditions and equation for the reaction.
(3)

IB Questionbank Chemistry 6
IB Questionbank Chemistry 7
 (ii) Explain the mechanism for the elimination of HBr from bromoethane.
(5)
(Total 8 marks)

12. The compounds H2NCH2CH2NH2 and HOOCCH2COOH react to form a polymer. What
is the structure of the repeating unit of the polymer?

A. ( HNCH2CONHCH2CH2NHCO )

B. ( HNCH2CH2NHCOCH2CO )

C. ( OCCH2CONHCH2NHCO )

D. ( HNCH2CH2NHCOCH2NH )
(Total 1 mark)

13. 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

(Total 1 mark)

14. 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)

IB Questionbank Chemistry 8
15. Halogenoalkanes undergo two major types of reaction leading to the formation of
different organic compounds.

(i) 1-bromopropane can be converted to 1-butylamine (butan-1-amine) in two

stages.
Draw the structural formulas of 1-bromopropane and 1-butylamine (butan-
1-amine).
(1)

(ii) Deduce a reaction pathway for the two-stage conversion of 1-bromopropane

to 1-butylamine (butan-1-amine). Your answer should include an equation for
each stage of the reaction and the reaction conditions for the second stage.
(4)
(Total 5 marks)

16. Which molecule has a chiral centre?

A. CH3CH=CHCHO

B. (CH3)2C=CHCH2OH

C. CH3OCH2CH3

D. CH3CHOHCH2CH3
(Total 1 mark)

17. 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)

IB Questionbank Chemistry 9
18. Which compound is optically active?

(Total 1 mark)

19. (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 10