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A bottle labelled ‘propanol’ contains one of two isomers of propanol - HSC - SSCE Chemistry - Question 27 - 2022 - Paper 1
Question 27
A bottle labelled ‘propanol’ contains one of two isomers of propanol. (a) Draw the TWO isomers of propanol. (b) Describe how 13C NMR spectroscopy might be used to ... show full transcript
Worked Solution & Example Answer:A bottle labelled ‘propanol’ contains one of two isomers of propanol - HSC - SSCE Chemistry - Question 27 - 2022 - Paper 1
Step 1
Step 2
Describe how 13C NMR spectroscopy might be used to identify which isomer is in the bottle.
Answer
The use of 13C NMR spectroscopy can help identify the isomer based on the number of distinct carbon environments in the molecule.
- Propan-1-ol will produce 3 signals because it has three different carbon environments.
- Propan-2-ol will produce 2 signals since it has a more symmetrical structure.
By analyzing the spectrum, if the bottle produces 2 signals, it indicates propan-2-ol, while 3 signals correspond to propan-1-ol.
Step 3
Write equations to represent the oxidation reactions of the two isomers. Include reaction conditions.
Answer
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Oxidation of Propan-1-ol (Propan-1-ol to Propanoic Acid):
CH3CH2CH2OH + [O] → CH3CH2COOH
Reaction conditions: Acidified potassium dichromate (H+/K2Cr2O7)
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Oxidation of Propan-2-ol (Propan-2-ol to Acetone):
CH3CHOHCH3 + [O] → CH3COCH3
Reaction conditions: Acidified potassium dichromate (H+/K2Cr2O7) or another suitable oxidizing agent.