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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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Most popular questions from this chapter

Question:Propose a molecular formula for rose oxide, a rose-scented compound isolated from roses and geraniums, which contains the elements of C, H, and O, has two degrees of unsaturation, and a molecular ion in its mass spectrum at m/z= 154.

Question:Match each structure to its mass spectrum.

Question: Reaction of BrCH2CH2CH2CH2NH2 with NaH forms compound W, which gives the IR and mass spectra shown below. Propose a structure for W and draw a stepwise mechanism that accounts for its formation.

Question: What cations are formed in the mass spectrometer by α cleavage of each of the following compounds?

Oxidation of citronellol, a constituent of rose and geranium oils, with PCC in the presence of added NaOCOCH3 forms compound A. A has a molecular ion in its mass spectrum at 154 and a strong peak in its IR spectrum at 1730 cm-1. Without added NaOCOCH3, oxidation of citronellol with PCC yields isopulegone, which is then converted to B with aqueous base. B has a molecular ion at 152, and a peak in its IR spectrum at 1680 cm-1.

a. Identify the structures of A and B.

b. Draw a mechanism for the conversion of citronellol to isopulegone.

c. Draw a mechanism for the conversion of isopulegone to B.
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