Introduction to organic chemistry

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Question 1
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This question is about isomers with the molecular formula C8H16O\text{C}_8\text{H}_{16}\text{O}C8​H16​O.

1.

Draw the skeletal formula of a branched chain ketone with molecular formula C8H16O\text{C}_8\text{H}_{16}\text{O}C8​H16​O that is optically active.

[1]
2.

Describe how you would distinguish between separate samples of the two enantiomers of this branched chain ketone.

[2]
3.

Draw the EEE and ZZZ forms of an acyclic alkenol structural isomer of C8H16O\text{C}_8\text{H}_{16}\text{O}C8​H16​O that shows both optical and geometric isomerism. Label each drawing clearly as EEE or ZZZ.

[2]
4.

Isomer L is cyclic and has an ether functional group (C−O−C\text{C}-\text{O}-\text{C}C−O−C). Isomer L has only four peaks in its 13C^{13}\text{C}13C NMR spectrum.

Skeletal representation of Isomer L, which is oxonane: a nine-membered cyclic ring consisting of one oxygen atom and eight carbon atoms. Because it possesses a plane of symmetry, only four peaks are visible in its 13C NMR spectrum.

Draw two other cyclic isomers of C8H16O\text{C}_8\text{H}_{16}\text{O}C8​H16​O that have an ether functional group and only four peaks in their 13C^{13}\text{C}13C NMR spectra.

[2]

Introduction to organic chemistry Questions

  1. A Level
  2. /Chemistry
  3. /Introduction to organic chemistry