4.14: Additional Exercises

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6-1 For the following compounds, star (*) each chiral center, if any.

6-2 For the following compounds, identify the R or S configuration of each chiral carbon atom.

6-3 Draw out the following molecules, including stereocenters.

a) (2R,4S,6R)-2-bromo-6-chloro-4-methylheptane

b) (4R)-4-bromopent-1-ene

c) (1R,2R,3S)-1-fluoro-2,3-dimethylcyclohexane

d) (3S)-3-methylcyclopent-1-ene

(R) and (S) Nomenclature of Asymmetric Carbon Atoms

6-4 For the following compounds, assign R or S configurations for each stereocenter.

6-5 For the following compounds, assign R or S configurations for each stereocenter.

6-6 Identify each molecule as either (R)- or (S)-Limonene.

Chiral Compounds Without Asymmetric Atoms

6-7 Explain why the following compound is optically active.

6-8 Does the following compound contain a chiral center? Is it a chiral molecule?

6-9 Why is this biaryl compound shown below considered chiral, despite having no chiral center?

Fischer Projections and Diastereomers

6-10 For the following Fischer projections, identify the configuration (R or S) of all chiral centers (some atoms may not be chiral centers).

6-11 For the following pairs of compounds, identify whether they are enantiomers, diastereomers, or the same compound.

6-12 For the following pairs of compounds, identify whether they are enantiomers, diastereomers, or the same compound.

Meso Compounds

6-13 For the following compounds, identify whether they are meso or not meso.

6-14 Are meso compounds optically active? Explain your answer.

6-15 Is the following compound meso or not meso?