AS Level · Chemistry 9701 · Organic chemistry

Halogen compounds: AS Level Chemistry questions with answers

Free Halogen compounds questions for AS Level Chemistry (9701), part of Organic chemistry. Each question has the answer and the marking points an examiner would look for.

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Halogen compounds practice questions

Question 1Multiple choice · 1 markA* challenge

Bromoethane is heated separately with aqueous NaOH and with NaOH in ethanol.
Which row shows the main organic products?

aqueous NaOHethanolic NaOH
Aethanolethanol
Bethanolethene
Cethanoic acidethene
Detheneethanol
Show answer

Answer: B

Question 2Multiple choice · 1 mark

Which term is described by this statement?
“A nucleophile replaces the halogen in a halogenoalkane.”

  1. A nucleophilic substitution
  2. B electrophile
  3. C amine
  4. D nucleophile
Show answer

Answer: A

Question 3Multiple choice · 1 markA* challenge

2-bromo-2-methylpropane and 1-bromobutane are each heated with aqueous sodium hydroxide.
Which row gives the mechanism for each?

2-bromo-2-methylpropane1-bromobutane
ASN2SN1
BeliminationSN2
CSN1SN2
DSN1SN1
Show answer

Answer: C

Question 4Structured · 8 marksA* challenge

2-bromopropane can be converted into propan-2-ol or propene depending on the conditions. In one experiment 7.38 g of 2-bromopropane gave 1.98 g of propan-2-ol.

(a)

State the conditions needed to make each product from sodium hydroxide.

[2]
(b)

State the role of the hydroxide ion in each reaction.

[2]
(c)

Calculate the percentage yield of propan-2-ol.

[2]
(d)

Explain why CFCs are unreactive in the lower atmosphere but cause damage in the stratosphere.

[2]
Show answers and mark scheme
PartAnswer and marking pointsMarks
(a)aqueous warm → alcohol; ethanolic hot → alkene
aqueous NaOH, warm → propan-2-ol B1
NaOH in ethanol, heat → propene B1
2
(b)nucleophile; base
nucleophile in substitution B1
base in elimination B1
2
(c)55.0%
n(2-bromopropane) = 0.0600 mol C1
yield = 55.0% A1
2
(d)strong C–F; UV releases Cl•
C–F (and C–Cl) bonds are strong so CFCs are unreactive M1
UV in the stratosphere breaks C–Cl to form Cl• radicals that break down ozone M1
2
Question 5Structured · 12 marks

This question is about the halogenoalkane 1-bromobutane, CH₃CH₂CH₂CH₂Br.

(a)

Classify this halogenoalkane as primary, secondary or tertiary.

[1]
(b)

State the reagent and conditions for converting it into an alcohol.

[2]
(c)

Describe the SN2 mechanism for this reaction. Show curly arrows, partial charges and any intermediate or transition state.

[4]
(d)

Explain why this halogenoalkane reacts by this mechanism rather than the other.

[2]
(e)

State the reagent and conditions needed to form an alkene from this halogenoalkane, and name the type of reaction.

[3]
Show answers and mark scheme
PartAnswer and marking pointsMarks
(a)primary
primary B1
1
(b)NaOH(aq); heat under reflux
aqueous sodium hydroxide B1
heat under reflux B1
2
(c)OH⁻ attacks δ+ C; transition state; Br⁻ leaves in one step
dipole on C–Br B1
curly arrow from lone pair of OH⁻ to δ+ carbon B1
curly arrow from C–Br bond to Br B1
transition state with partial bonds and negative charge B1
4
(d)primary carbocation unstable; little steric hindrance
a primary carbocation would be unstable (only one alkyl group) B1
the carbon is not sterically hindered so OH⁻ can attack directly B1
2
(e)NaOH in ethanol; heat; elimination
sodium hydroxide dissolved in ethanol B1
heat B1
elimination B1
3
Question 6Structured · 3 marks

Halogenoalkanes can undergo elimination.

(a)

State the conditions for elimination rather than substitution.

[2]
(b)

Name the organic product when 2-bromopropane undergoes elimination.

[1]
Show answers and mark scheme
PartAnswer and marking pointsMarks
(a)ethanolic NaOH; heat
NaOH in ethanol B1
heat B1
2
(b)propene
propene B1
1

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