Organic Chemistry / IR Spect: Frequencies Considering Solution Effects
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Solution: When two substituents are on the same side of a ring skeleto...

Question

When two substituents are on the same side of a ring skeleton, they are said to be cis, and when on opposite sides, trans (analogous to use of those terms with 1,2-disubstituted alkene isomers). Consider stereoisomeric forms of 1,2-cyclopentanediol (compounds having a five-membered ring and hydroxyl groups on two adjacent carbons that are cis in one isomer and trans in the other). At high dilution in CCl4, both isomers have an infrared absorption band at approximately 3626 cm-1 but only one isomer has a band at 3572 cm -1.

(a) Assume for now that the cyclopentane ring is coplanar (the interesting actuality will be studied later) and then draw and label the two isomers using the wedge–dashed wedge method of depicting the OH groups.