Wolmer’s High School for Girls

Six Form Chemistry

1. The isomers A and B have the molecular formula, C9H8O2. They are insoluble in water
but soluble in aqueous sodium carbonate. Both A and B are reduced by hydrogen in the
presence of a platinum catalyst to C, C9H10O2. Benzoic acid is formed when A
or B or C is oxidized by alkaline potassium manganate (VII), and the solution is later
acidified. C reacts with phosphorus (V) chloride to give D, and reacts with sodium carbonate
solution to give carbon dioxide.

Identify and draw displayed formula the compounds A to D

(4 marks)

2. Two isomeric phenyl alcohols, A and B, (C8H10O), on treatment with concentrated

sulphuric acid produced Compound D, which decolourized a solution of bromine in an
organic solvent. Oxidation of the isomers with acidified potassium dichromate (VI)
produced compounds E and F which both gave yellow precipitates with 2,4-DNP
reagent. However, only Compound F formed a silver mirror with a solution of silver
nitrate.

(i) State the type of reaction that produced Compound D and write its structural formula.

Type of reaction

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Structural formula of Compound D

(2 marks)

(ii) Explain the reactions which led to the production of Compounds E and F.

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(2 marks)
 (c ) Deduce the structural formulae of compounds.
(i) E and F

(2 marks)

(ii) A and B

(2marks)

(d) Comment on the reaction of A and B to plane polarized light.

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(1 mark)

4. The molecular formulae of some compunds that can be prepared from ethanoic acid are
given in the scheme below.

C2H4O2
Ethanoic acid

Ethanol/conc H2SO4/heat PCl5

C4H8O2 C2H3O2Na C2H3OCl C2H5ON

P Q R S

a. (i) Give the name and structural formula of P.

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(iii) Give the name of the type of reaction which occurs when P is formed from ethanoic
acid.

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 a. Ethanoic acid can be obtained from P.

(i) Give the names of the reagent(s) and state the condition required.

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(ii) Write a balanced equation for the reaction.

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5. Suggest simple one-step test tube reactions by which the isomers in the following pairs
can be distinguished from each other. You should state the reagents and conditions for
each test and describe how each of the isomer in the pair behaves.

(i) CH3CH(OH)CH3 and CH3CH2CH2OH

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(ii) CH3COCH3 and CH3=CHCH2OH

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(iii) CH3CH2COCH2CH3 and CH3CH2CH2CH2CHO

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(iv) CH3CH2CO2H and CH3COCH2OH

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