Chirality and Aldehyde homework

1. An alcohol with the molecular formula C4H9OH is chiral.

(i) Explain what is meant by the term chiral.

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(ii) Draw two diagrams to clearly represent the optical isomers that result from the chirality of
this alcohol.

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(iii) Explain how you could distinguish between these two isomers experimentally.

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2. Compounds produced when glucose C6H12O6, is metabolised include:

CH2(OH)CH(OH)CHO CH3COCOOH CH3CH(OH)COOH

(i) Draw the full structural formula for 2,3-dihydroxypropanal.

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(ii) Suggest two of these compounds which would give a positive test with 2,4-
dinitrophenylhydrazine solution. State what you would see for a positive test result.

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(iii) Describe a test which would enable you to distinguish between the two compounds
identified in part (ii).

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3. Propenal, CH2=CHCHO, is one of the materials that gives crispy bacon its sharp odour. In the following
question assume that the carbon–carbon double bond and the aldehyde group in propenal behave
independently.

(a) Give the structural formulae of the compounds formed when propenal reacts with:

(i) hydrogen bromide;

(ii) hydrogen cyanide;

(iii) 2,4-dinitrophenylhydrazine.
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(b) (i) Give the mechanism for the reaction between hydrogen cyanide and the aldehyde group.
You may represent the aldehyde group as

R
C O
H
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(ii) The reaction in (i) occurs best in slightly acidic conditions. It is slower if the pH is high or
low. Suggest reasons why this is so.

High pH ……………………………………………………………………….

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Low pH ………………………………………………………………………..

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(c) Explain why lithium tetrahydridoaluminate(III) (lithium aluminium hydride), LiAlH4, reacts only
with the >C=O bond and not with the >C=C< bond, even though these bonds have the same
electronic structure.

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(d) Suggest reactions, giving equations and conditions, which would convert propenal into a
compound which would react with iodine in the presence of sodium hydroxide solution.
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