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Compound X has the molecular formula C4H8O2 - CIE - A-Level Chemistry - Question 5 - 2012 - Paper 1

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Compound X has the molecular formula C4H8O2. (a) (i) Treatment of X with sodium metal produces a colourless flammable gas. What does this result tell you about ... show full transcript

Worked Solution & Example Answer:Compound X has the molecular formula C4H8O2 - CIE - A-Level Chemistry - Question 5 - 2012 - Paper 1

Step 1

Treatment of X with sodium metal produces a colourless flammable gas.

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Answer

The reaction with sodium metal indicates that X contains a functional group that can release hydrogen gas, which suggests the presence of either a carboxylic acid or alcohol. Since sodium reacts with these functionalities to produce hydrogen, the functional groups could be either a carboxylic acid (-COOH) or alcohol (-OH).

Step 2

There is no reaction when X is treated with sodium hydrogen carbonate, NaHCO3.

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Answer

The lack of reaction with sodium hydrogen carbonate suggests that X does not contain a carboxylic acid group. Carboxylic acids typically react with sodium bicarbonate to produce carbon dioxide, whereas other functional groups, including alcohols, do not. Therefore, X may only contain an alcohol or other functional groups that do not react with NaHCO3.

Step 3

When X is shaken with aqueous bromine the orange colour disappears.

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Answer

The decolorization of bromine indicates the presence of a double bond, which is a characteristic of alkenes. The bromine reacts across the double bond, leading to the loss of color. This suggests that X must contain a C=C double bond (alkene functionality) in addition to the hydroxyl group.

Step 4

Draw displayed formulae of each of these two pairs.

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Answer

For pair 1:

  1. H H | | H--C==C--O--H | | H H

  2. H H | | H--C==C--OH | | H H

For pair 2:

  1. H H | | H--C--C--OH | | H *

  2. H H | | H--C--C--OH | |

    • H

where * denotes a chiral carbon atom.

Step 5

These four isomers of X show two types of stereoisomerism. State which type of isomerism each pair shows.

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Answer

For pair 1, the isomers exhibit geometrical isomerism (also known as cis-trans or E/Z isomerism). For pair 2, the isomers demonstrate optical isomerism due to the presence of one or more chiral centers.

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