Paper 2 DP2 HL T2 2019

1a. [1 mark]

Geometrical isomerism and optical isomerism are two sub-groups of stereoisomerism in organic
chemistry.

Describe what is meant by the term stereoisomers.

Markscheme

compounds with same structural formula but different arrangements of atoms in space;

Award [1] if correct description of geometric and optical isomers given.

1b. [2 marks]

Compound P has the following three-dimensional structure. P also has geometrical isomers.

Draw any two other isomers of P.

Markscheme

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1c. [2 marks]

Apply IUPAC rules to state the names of all the straight-chain isomers of compounds of molecular
formula C4H8 (including P).

Markscheme

trans-but-2-ene and cis-but-2-ene;

Allow trans 2-butene and cis 2-butene.

Do not accept just 2-butene or 2-butene.

but-1-ene;

Allow 1-butene.

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1d. [4 marks]

State the structural formula of the organic products, Q, R, S and T, formed in the following reactions.

Markscheme

Q: ;

R: ;

S: ;

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 T: ;

Condensed or full structural formulas may be given.

1e. [1 mark]

State the structural formula of the organic product formed when compound R is heated under reflux
with acidified potassium dichromate(VI).

Markscheme

Condensed or full structural formula may be given.

1f. [1 mark]

Apply IUPAC rules to state the name of this product, U.

Markscheme

butan-2-one;

Allow 2-butanone or butanone.

Accept butan-2-one if (v) is incorrect but also apply ECF.

1g. [2 marks]

Menthol can be used in cough medicines. The compound contains C, H and O only.

Alanine is a 2-amino acid occurs that naturally and has several isomers. State the structural feature of
alanine which is responsible for it having enantiomers and draw the enantiomer in the space provided.

Markscheme

chiral (carbon/centre/atom) / (tetrahedral) carbon surrounded by four

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 different groups; Accept chiral compound or chiral molecule;

Mirror drawing

MUST have correct bonding H2N----C

1h. [1 mark]

State the instrument used to distinguish between each of the two enantiomers, and how they could be
distinguished using this instrument.

Markscheme

polarimeter and (enantiomers) rotate plane of polarized light in (equal and) opposite directions;

2a. [1 mark]

Halogenoalkanes undergo nucleophilic substitution reactions with sodium hydroxide.

State a reason why most halogenoalkanes are more reactive than alkanes.

Markscheme

polarity/polar «molecule/bond»
OR
carbon–halogen bond is weaker than C–H bond ✔

2b. [1 mark]

Classify 1-bromopropane as a primary, secondary or tertiary halogenoalkane, giving a reason.

Markscheme

primary AND Br/bromine is attached to a carbon bonded to two hydrogens

OR
primary AND Br/bromine is attached to a carbon bonded to one C/R/alkyl «group» ✔

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 Accept “primary AND Br/bromine is attached to the first carbon in the chain”.

2c. [4 marks]

Explain the mechanism of the reaction between 1-bromopropane with aqueous sodium hydroxide
using curly arrows to represent the movement of electron pairs.

Markscheme

Or the official

curly arrow going from lone pair/negative charge on O in HO – to C ✔

curly arrow showing Br leaving ✔

representation of transition state showing negative charge, square brackets and partial bonds ✔

formation of organic product CH3CH2CH2OH AND Br– ✔

Do not allow curly arrow originating on H in HO–.

Accept curly arrow either going from bond between C and Br to Br in 1-bromopropane or in the
transition state.

Do not penalize if HO and Br are not at 180° to each other.

Do not award M3 if OH–C bond is represented.

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2d. [1 mark]

State, giving your reason, whether the hydroxide ion acts as a Lewis acid, a Lewis base, or neither in the
nucleophilic substitution.

Markscheme

«Lewis» base AND donates a pair of electrons ✔

2e. [2 marks]

Suggest two advantages of understanding organic reaction mechanisms.

Markscheme

Any two of:

choose «most» appropriate reaction «for preparing the target compound» ✔
design/discover new reactions/reagents ✔
apply this knowledge to other areas of chemistry/science ✔
«retro-»synthesis «more effective» ✔
control/predict «desired» products ✔
control rate of reaction «more effectively» ✔
satisfy intellectual curiosity ✔
predicting how changing reagents/conditions might affect reaction ✔
suggesting intermediates/transition states ✔

Accept other reasonable answers.

3a. [1 mark]

This question is about carbon and chlorine compounds.

Ethane, , reacts with chlorine in sunlight. State the type of this reaction and the name of the
mechanism by which it occurs.

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 Markscheme

substitution AND «free-»radical

OR

substitution AND chain

Award [1] for “«free-»radical substitution” or “SR” written anywhere in the answer.

[1 mark]

3b. [3 marks]

Formulate equations for the two propagation steps and one termination step in the formation of
chloroethane from ethane.

Markscheme

Two propagation steps:

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 One termination step:

OR

OR

Accept radical without if consistent throughout.

Allow ECF for incorrect radicals produced in propagation step for M3.

[3 marks]

3c. [1 mark]

Deduce the splitting patterns in the 1H NMR spectrum of C2H5Cl.

Markscheme

triplet AND quartet

[1 mark]

3d. [2 marks]

One possible product, X, of the reaction of ethane with chlorine has the following composition by mass:

carbon: 24.27%, hydrogen: 4.08%, chlorine: 71.65%

Determine the empirical formula of the product.

Markscheme

AND AND

«hence» CH2Cl

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 Accept : :

Do not accept C2H4Cl2.

Award [2] for correct final answer.

[2 marks]

3e. [3 marks]

The mass and 1H NMR spectra of product X are shown below. Deduce, giving your reasons, its structural
formula and hence the name of the compound.

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Markscheme

molecular ion peak(s) «about» m/z 100 AND «so» C2H4Cl2 «isotopes of Cl»

two signals «in 1H NMR spectrum» AND «so» CH3CHCl2

OR
«signals in» 3:1 ratio «in 1H NMR spectrum» AND «so» CH3CHCl2
OR
one doublet and one quartet «in 1H NMR spectrum» AND «so» CH3CHCl2

1,1-dichloroethane

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 Accept “peaks” for “signals”.

Allow ECF for a correct name for M3 if an incorrect chlorohydrocarbon is identified.

[3 marks]

3f. [1 mark]

Chloroethene, , can undergo polymerization. Draw a section of the polymer with three
repeating units.

Markscheme

Continuation bonds must be shown.

Ignore square brackets and “n”.

Accept .

Accept other versions of the polymer, such as head to head and head to tail.

Accept condensed structure provided all C to C bonds are shown (as single).

[1 mark]

4a. [2 marks]

Organic compounds often have isomers.

A straight chain molecule of formula C5H10O contains a carbonyl group. The compound cannot be
oxidized by acidified potassium dichromate(VI) solution.

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 Deduce the structural formulas of the two possible isomers.

Markscheme

Accept condensed formulas.

[2 marks]

4b. [2 marks]

Mass spectra A and B of the two isomers are given.

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Explain which spectrum is produced by each compound using section 28 of the data booklet.

Markscheme
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 A:

CH3CH2COCH2CH3 AND «peak at» 29 due to

(CH3CH2)+/(C2H5)+/(M – CH3CH2CO)+

OR

CH3CH2COCH2CH3 AND «peak at» 57 due to

(CH3CH2CO)+/(M – CH3CH2)+/(M – C2H5)+

B:

CH3COCH2CH2CH3 AND «peak at» 43 due to

(CH3CH2CH2)+/(CH3CO)+/(C2H3O)+/(M – CH3CO)+

Penalize missing “+” sign once only.

Accept “CH3COCH2CH2CH3 by elimination since fragment CH3CO is not listed” for M2.

[2 marks]

4c. [2 marks]

Nitrobenzene, C6H5NO2, can be converted to phenylamine via a two-stage reaction.

In the first stage, nitrobenzene is reduced with tin in an acidic solution to form an intermediate ion and
tin(II) ions. In the second stage, the intermediate ion is converted to phenylamine in the presence of
hydroxide ions.

Formulate the equation for each stage of the reaction.

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Markscheme

Stage one:

C6H5NO2(l) + 3Sn(s) + 7H+(aq) → C6H5NH3+(aq) + 3Sn2+(aq) + 2H2O(l)

Stage two:

C6H5NH3+(aq) + OH–(aq) → C6H5NH2(l) + H2O(l)

[2 marks]

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