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ago in Organic Chemistry by (350 points)
Identify the number of stereoisomers for the compound 1,2-dichlorocyclopentane, and draw the structures for each stereoisomer, indicating which one is a meso compound.

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1,2-dichlorocyclopentane has two chiral carbons, which means there can be a maximum of 2^n stereoisomers, where n is the number of chiral centers. In this case, n=2, so there can be a maximum of 2^2 = 4 stereoisomers. However, one of these stereoisomers is a meso compound, which means it has an internal plane of symmetry and is optically inactive. Therefore, there are actually only 3 unique stereoisomers for 1,2-dichlorocyclopentane.Here are the structures for each stereoisomer:1.  1R,2R -1,2-dichlorocyclopentane   H       Cl    \     /     C1---C2    /     \   H       Cl2.  1S,2S -1,2-dichlorocyclopentane   Cl      H    \     /     C1---C2    /     \   Cl      H3. Meso-1,2-dichlorocyclopentane  1R,2S or 1S,2R    H       Cl    \     /     C1---C2    /     \   Cl      HIn these structures, C1 and C2 are the chiral centers, and the stereochemistry is indicated by the R and S configurations. The meso compound is the third structure, where the compound has an internal plane of symmetry and is optically inactive.
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