Section B

Answer ALL questions in the spaces provided.

1. (a) Define the term ‘structural isomerism’.

Compounds with the same molecular formula but different arrangement of atoms/structural
formulae

(b) 60cm3 of oxygen were mixed with 10cm3 of a gaseous hydrocarbon, X, CxHy. After
exploding and cooling to room temperature, 40cm3 of gas were left. On shaking with aqueous
sodium hydroxide, 10cm3 of oxygen remained. (All measurements were made at the same
conditions of temperature and pressure.) The combustion of X can be represented by the
following equation:

(i) Calculate the formula of the hydrocarbon, X.

n of hydrocarbon = 1 mole
n of oxygen = 5 moles (6-1) [1 mark]
n of CO2 = 3 moles, n of CO2 = n of C = 3 [1 mark]
n of H2O = 4 (based on balanced equation), n of H = 2xH2O = 8 [1 mark]
X = C3H8 [1 mark]
[4 marks]
(ii) Hence, write its displayed formula.

[1 mark]

(c) There are four alcohols with the molecular formula C4H10O. The formulae for two of them
are:

(i) Write the name and displayed formula for EACH of the other two alcohols.

“NOTHING LIMITS EXCELLENCE”

 2-methylpropanol 2-methyl-2-propanol (1/2 mark for each correct
formula and name) [2 marks]

(ii) When butan-2-ol is heated with phosphoric acid, a mixture of alkenes is produced.
One of these alkenes exhibits isomerism.

Write the names and displayed formulae of the two isomers of this alkene.

cis and trans but-2-ene (1/2 mark for each correct formula and name) [2 marks]

(d) Table 1 shows two pairs of compounds. Complete the table by describing simple laboratory
tests to distinguish between EACH pair of compounds.

1st pair – add NaOH [1 mark] followed by I2 [1 mark], yellow ppt/antiseptic smell forms with 1st
compound only [1 mark]

2nd pair – add acidified KMnO4/K2Cr2O7 [1 mark], solution goes purple to colorless/orange to
green with 1st compound only [1 mark] OR add NaOH [1 mark] followed by I2 [1 mark], yellow
ppt/antiseptic smell forms with 1st compound only [1 mark]

2. Figure 1 shows the reaction sequence of an organic compound, A, producing compounds B

and C.

(a) Identify the reaction mechanisms leading to Compound

B - Electrophilic addition [1 mark]
C - Nucleophilic substitution [1 mark]

(b) Draw the displayed formula for EACH of the following compounds:

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 B-

[1 mark]

C-
[1 mark]

(c) Using curved arrows to show the movement of electrons, write the mechanism for the
conversion of Compound A to Compound B.
Mechanism as outlined below with X = Br

Dipoles shown in H-Br and breaking of bond heterolytically [1 mark]

Correct arrows showing electrons attacking H on HBr [1 mark]
Hydrogen goes on to carbon with greater hydrogen atoms and tertiary carbocation shown
[1 mark]
Correct arrow for Br- attacking carbocation [1 mark]
[4 marks]

(d) State the name and reagents for a laboratory test that can be used to distinguish between
Compound C and propan-1-ol.

Name – oxidation [1 mark]

Reagents – KmnO4/H+ OR K2Cr2O7/H+

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 (e) A student performed a number of tests to identify various functional groups. Table 2
shows an incomplete laboratory record of the investigation. Complete the record by
inserting the appropriate observations.
(i) White fumes/choking or irritating odor/effervescence or bubbling/violent or
vigorous reaction/lots of heat given off [any 2 – 2 marks]
(ii) Yellow ppt [1 mark]
(iii) Bromine decolorizes/white ppt/antiseptic smell [any 1 – 1 mark]
(iv) Bromine decolorizes/2 colorless immiscible layers formed [1 mark]

3. The following diagram represents some of the reactions of benzene.

(a) State the type of reactions labelled I and IV.
Reaction I - Electrophilic substitution [1 mark]
Reaction IV - Diazotization [1 mark]

(b) List the reagents and conditions required for Reactions II and IV.
Reaction II
Reagents: conc. HNO3, conc H2SO4 [1 mark]
Conditions: temperature below 50oC [1 mark]

Reaction IV
Reagents: HNO2/H+ OR NaNO2 and HCl [1 mark]
Conditions: temperature below 10oC [1 mark]

(c) Draw the displayed formula for Compound X.

[1 mark]

(d) Outline the mechanism for Reaction I using curved arrows to indicate the movement of
electrons, being careful to identify the various steps involved.
Mechanism as outlined below using Br instead of Cl

Step 1 – correct arrow from bezene ring to Br+ [1 mark], resonance stabilization of
positive charge [1 mark]

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 Step 2 – correct arrow showing removal of H+ by nucleophile [1 mark], correct arrow
showing movement of electron from H into benzene ring [1 mark]

(e) Write the structural formula for the products formed when phenol is treated with

(i) Aqueous bromine

(ii) Sodium hydroxide

(iii) Ethanoyl chloride

(f) Write the equation for the reaction in (e) (iii).