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Chapter 13: Q 50. (page 525)

Question:A chiral compound Y has a strong absorption at 2970–2840 cm-1in its IR spectrum and gives the following mass spectrum. Propose a structure for Y.

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01

IR Frequency

Thechiral compound Y has a strong absorption at 2970–2840 cm-1 in its IR spectrum due to sp3 hybridized C–H bonds.At the frequency region 2970–2840 cm-1 the -CH2group is present.

02

Mass spectra

Thetwo peaks of equal intensity at 136 and 138 indicate the presence of a Br atom. These bonds have high polarity and are strong.

03

Determination of the structure

The m/z value of mass spectra is identified by the atom present in the structure, and IR spectra are identified by the functional group present in structure.

The base peak 136 and 138 sp3hybridized -CH2bonds are present in the structure; the molecular formula is C4H9Br.

Two possible structures of C4H9Br

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