Question 13.3: Fischer Projections Determine if each Fischer projection is ...

Fischer Projections

Determine if each Fischer projection is chiral or achiral. If chiral, identify it as the D or L stereoisomer and draw the mirror image.

a. CH2OHHO  H CH3 b.CH3HO  H CH3 \begin{array}{r c}\begin{matrix} \quad CH_2OH \end{matrix} \\ \begin{matrix} HO \end{matrix} \begin{array}{r|c} \begin{matrix} \\ \end{matrix} & \begin{matrix} \\ \end{matrix} \\ \hline \begin{matrix}  \\ \end{matrix} & \begin{matrix}  \\ \end{matrix}\end{array}H \\\begin{matrix}\quad \quad \ CH_3 \end{matrix}&&&&&&  b. \begin{matrix} \quad CH_3 \end{matrix} \\&&&&&& \begin{matrix} HO \end{matrix} \begin{array}{r|c} \begin{matrix} \\ \end{matrix} & \begin{matrix} \\ \end{matrix} \\ \hline \begin{matrix}  \\ \end{matrix} & \begin{matrix}  \\\end{matrix}\end{array}H \\&&&&&&\begin{matrix}\quad \quad \ CH_3 \end{matrix}\end{array}

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a. Chiral. The carbon at the intersection is attached to four different substituents. It is the L stereoisomer because the —OH group is drawn on the left. The mirror image is drawn by reversing the —H and —OH groups on the chiral carbon.

CH2OHH  OH  CH3\begin{matrix} \quad CH_2OH \end{matrix} \\ \begin{matrix} H \end{matrix} \begin{array}{r|c} \begin{matrix} \\ \end{matrix} & \begin{matrix} \\ \end{matrix} \\ \hline \begin{matrix}  \\ \end{matrix} & \begin{matrix}  \\ \end{matrix}\end{array}OH \\\begin{matrix}\quad  \ CH_3 \end{matrix}

b. Achiral. The carbon atom at the intersection is attached to two identical groups (CH3-CH_{3}).

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