Problem: 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.(b) Designate which isomer will have the 3572-cm -1 band and explain its origin.

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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.

(b) Designate which isomer will have the 3572-cm -1 band and explain its origin.

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