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An organic chemist found a bottle in the laboratory that was labelled 'organic cleaning fluid, C₆H₁₄O' - VCE - SSCE Chemistry - Question 5 - 2012 - Paper 1
Question 5
An organic chemist found a bottle in the laboratory that was labelled 'organic cleaning fluid, C₆H₁₄O'. She decided to test the liquid. The chemist obtained the foll... show full transcript
Worked Solution & Example Answer:An organic chemist found a bottle in the laboratory that was labelled 'organic cleaning fluid, C₆H₁₄O' - VCE - SSCE Chemistry - Question 5 - 2012 - Paper 1
Step 1
Step 2
Step 3
In the ¹H NMR spectrum, the signal at 3.6 ppm is split into a septet (7 peaks). What is the number of equivalent protons that are bonded to the adjacent carbon atom(s)?
Answer
The signal at 3.6 ppm indicates that there are 6 equivalent protons bonded to the adjacent carbon atom, as the splitting pattern of a septet suggests that there are 6 neighboring protons (n) which can be calculated using the n + 1 rule.
Step 4
Using the Infrared absorption data on page 7 of the Data Book, identify the atoms that are associated with the absorption labelled A on the infrared spectrum.
Answer
The absorption labelled A in the infrared spectrum corresponds to the O-H stretching vibration, indicating the presence of hydroxyl (-OH) groups in the compound.
Step 5
Draw a structure of the compound in the cleaning fluid that is consistent with the NMR and IR data.
Answer
The structure of the compound can be represented as an alcohol with the formula C₆H₁₄O, which includes the functional group corresponding to the ¹H NMR and IR data. A common structure could be hexanol where one of the carbons bears the hydroxyl group.