5. Chirality

In this attempt to convert the line angle drawing of d-erythrose (shown) to the Fischer projection (shown), by viewing it from a certain direction (shown), a mistake was made. What was the mistake?

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Convert the line-angle drawings into Fischer projections.

(a)

Which of the following compounds are chiral? Draw each compound in its most symmetric conformation, star (*) any asymmetric carbon atoms, and draw any mirror planes. Label any meso compounds. You may use Fischer projections if you prefer.

(e) (R,R)-2,3-dibromobutane

(f)

For each Fischer projection,

1. make a model.

2. draw the mirror

3.. determine whether the mirror is the same as, or different from, the original ­structure.

4. draw any mirror planes of symmetry that are apparent from the Fischer projections.

(c)

(d)

Draw Fischer projections of the following molecules.

(c)

Which Fischer projection represents $D$-glucose?

Which of the following is the correct Fischer projection for $D_{-}\mathrm{glucose}$?

Which of the following choices represents the Fischer projection of $C_2{H}_{6}O$ (ethanol)?

Which of the following choices represents the Fischer projection of $2_{-}\mathrm{butanol}$?

Which of the following is a correct Fischer projection for $D_{-}\mathrm{glucose}$?

Convert the following perspective formulas to Fischer projections.

(c)

(d)

Given the following compound: ${\mathrm{CH}}_3-\mathrm{CH}\left(\mathrm{OH}\right)-\mathrm{CH}\left(\mathrm{Cl}\right)-\mathrm{COOH}$, which of the following Fischer projections correctly represents this molecule?

Given the wedge-and-dash structure of $2_{}$-bromobutanol with the following configuration: the hydroxyl group ($\mathrm{OH}$) is on a wedge at carbon 2, the bromine ($\mathrm{Br}$) is on a dash at carbon 2, and the methyl group ($\mathrm{CH}{3}_{}$) and hydrogen are in the plane, which Fischer projection correctly represents this molecule?

Which of the following correctly represents the Haworth projection of the $\alpha$-pyranose form of $D$-glucose derived from its Fischer projection?

Draw Fischer projections of the following molecules.

(a)