TOPIC 15: ORGANIC CHEMISTRY: CARBONYLS, CARBOXYLIC ACIDS AND CHIRALITY

1 Compound D, C4H6O, reacts with 2.4-dinitrophenylhydrazine to form an orange precipitate.

Compound D is oxidised by acidified potassium dichromate(VI) to form compound E.
Compound D is reduced by lithium aluminium hydride to form compound F.
Compound E reacts with aqueous sodium hydroxide to form compound G.
Deduce the identities of compounds D, E, F and G. (4)

D …………………………………………….. E …………………………………………………..

F …………………………………………….. G …………………………………………………..
(Total for Question 1 = 4 marks)

2 Ethanol, CH3CH2OH, reacts with 2-methylbutanoic acid, CH3CH2CH(CH3)COOH, to form an

ester that is found in ripe apples.

(a) Give the structural formula of the ester formed. (1)

(b) A similar ester, CH3COOCH2CH2CH(CH3)2, is also found in ripe apples.

Give the structural formulae of the carboxylic acid and the alcohol that could be used to
make this ester. (2)

Carboxylic acid:

Alcohol:

(c) (i) Give the structural formula for the repeat unit of the polymer formed between
HO(CH2)2OH and HOOC(CH2)6COOH. (1)

(ii) Give the name of this type of polymerisation. (1)

(Total for Question 2 = 5 marks)

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3 The three compounds shown can be distinguished by simple chemical tests.

CH3CH2CH2CHO CH3CH2COCH3 CH3CH2COOH

A B C

(a) Identify a reagent that reacts only with A. State the observation that would be made with this
reagent. (2)

Reagent:

Observation:

(b) Identify a reagent that reacts only with B. State the observation that would be made with this
reagent. (2)

Reagent:

Observation:

(c) Identify a reagent that reacts only with C. State the observation that would be made with this
reagent. (2)

Reagent:

Observation:
(Total for Question 3 = 6 marks)

4 The compound 2-hydroxypropanenitrile, CH3CH(OH)CN, has a chiral centre and can display
optical isomerism.

(a) State what is meant by the term chiral centre. (1)

(b) Show the two optical isomers of CH3CH(OH)CN by completing the diagrams. (2)

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 (c) Describe how you could distinguish between the two opitcal isomers. (2)

(Total for Question 4 = 5 marks)

TOTAL FOR ASSESSMENT = 20 MARKS

© Pearson Education Ltd 2019. Copying permitted for purchasing institution only. This material is not copyright free. This
document may have been altered from the original.