16. Stereoisomers of 1,3-dichlorocyclopentane Cyclopentane ring is essentially p

Question

16. Stereoisomers of 1,3-dichlorocyclopentane

Cyclopentane ring is essentially planar. 1,3-dichlorocyclopentane has two stereocentres. Cis-1,3-dichlorocyclopentane is a meso compound due to a plane of symmetry passing right through the C-2 and bisecting the C-4, C-5 bond.

Trans-1,3-dichlorocyclopentane exist as a pair of enantiomers as shown in the figure 1.

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17. Both compounds have two chiral centres each.

Draw the structure of first compound and also draw its mirror image without paying attention the second structure given in the question. Now try to match the mirror image with the second structure given in the question. It becomes clearly evident that both the given compounds are mirror images of each other.

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Apply second method also to make sure that your answer is correct. Assign the configuration to the carbon bearing methyl group. It comes out to be R in left hand side structure.

Also assign the configuration to the same carbon in the second compound, it comes out to be S. Mirro image of a chiral carbon has opposite configuration. Therefore, it also confirms that both are enantiomers.

As shown in the figure 2, the two compounds given in the question are a pair of enantiomers.  

Explanation / Answer

16 17

piet), 6.1 (2H, doublet) (ppm) 16. Draw the stereoisomers of 1,3-dichlorocyclopentane. 17. Which of the following terms best describes the pair of compounds shown: enantiomes diastereomers, or the same compound? CHs Ho

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