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CHEMISTRY, M7 2015 VCE 5b

Draw the full structural formula of an isomer of butan-2-ol.   (1 mark)

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Possible images include:

                
 

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Possible images include:

                
 

CHEMISTRY, M7 2019 HSC 21

  1. The structural formula for 2-methylpropan-2-ol is shown in the table.
  2. Draw one structural isomer of this alcohol and state its name.   (2 marks)

     

     

  3. The structural formulae for two compounds are shown below.
     

   
 

  1. Why are these two compounds classed as functional group isomers?   (2 marks)

  2. A chemical test is required to distinguish between the isomers in part (b).
  3. Identify a suitable test and explain the expected observations.   (3 marks)

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a.   Successful answers should have one of the following:

 

b.  Functional Group isomers

→ Both isomers have the same number and type of atoms, but they have different arrangements of those atoms and therefore have different functional groups.

→ Isomer A has a ketone functional group, while isomer B has an aldehyde functional group.
 

c.   Tollens’ Test:

→ The Tollens’ test can be used to differentiate between Isomer A (a ketone) and Isomer B (an aldehyde).

→ Isomer B will be readily oxidised to a carboxylic acid, whereas isomer A will not.

→ As a result, Isomer B will reduce the silver-ions in Tollens’ reagent to form a silver mirror inside the test tube, while Isomer A will not react.

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a.   Successful answers should have one of the following:

b.  Functional Group isomers

→ Both isomers have the same number and type of atoms, but they have different arrangements of those atoms and therefore have different functional groups.

→ Isomer A has a ketone functional group, while isomer B has an aldehyde functional group.
 

c.   Tollens’ Test:

→ The Tollens’ test can be used to differentiate between Isomer A (a ketone) and Isomer B (an aldehyde).

→ Isomer B will be readily oxidised to a carboxylic acid, whereas isomer A will not.

→ As a result, Isomer B will reduce the silver-ions in Tollens’ reagent to form a silver mirror inside the test tube, while Isomer A will not react.


♦♦ Mean mark (c) 39%.

CHEMISTRY, M8 2022 HSC 27

A bottle labelled 'propanol' contains one of two isomers of propanol.

  1. Draw the TWO isomers of propanol.   (2 marks)
     

  1. Describe how spectroscopy might be used to identify which isomer is in the bottle.   (2 marks)
  1. Each isomer produces a different product when oxidised.
  2. Write equations to represent the oxidation reactions of the two isomers. Include reaction conditions.   (3 marks)
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a.    Isomer 1:

Isomer 2:

b.   Identifying isomers with spectroscopy:

→ this can be used to identify the isomers in the bottle because they show a different number of signals which helps deduce the carbon environment.

→ Propan-1-ol contains 3 environments so it would have 3 peaks on a spectrum whereas propan-2-ol only contains 2 environments (due to symmetry), so it would only have 2 signals on a spectrum.

c.  


  

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a.    Isomer 1:

   

Isomer 2:

   

b.   Identifying isomers with spectroscopy:

→ this can be used to identify the isomers in the bottle because they show a different number of signals which helps deduce the carbon environment.

→ Propan-1-ol contains 3 environments so it would have 3 peaks on a spectrum whereas propan-2-ol only contains 2 environments (due to symmetry), so it would only have 2 signals on a spectrum.

c.  


  


♦ Mean mark (c) 52%.