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Chapter 13: Q 43. (page 523)

Question: How would each of the following pairs of compounds differ in their IR spectra?

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01

IR Spectra

In IR spectroscopy, each functional group has its wavelength. Each functional absorbs a different wavelength, and thus functional groups are characterized by IR spectroscopy.

02

Differentiation of functional group

The IR absorption frequencies of the bonds are: Csp2 -H at 3150–3000cm-1 and C sp-H at 3300 cm-1.

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Most popular questions from this chapter

Question: What is the mass of the molecular ion formed from compounds having each molecular formula:

(a) C3H6O; (b)C10H20;(c)C8H8O2; (d) methamphetamine (C10H15N)?

Question: Reaction of tert-butyl pentyl ether [CH3CH2CH2CH2CH2OC(CH3)3]with HBr forms 1-bromopentane(CH3CH2CH2CH2CH2Br) and compound B. B has a molecular ion in its mass spectrum at 56 and gives peaks in its IR spectrum at 3150–3000, 3000–2850, and 1650 cm-1. Propose a structure for B and draw a stepwise mechanism that accounts for its formation.

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: Explain why a carbonyl absorption shifts to lower frequency in an α,β-unsaturated carbonyl compound—a compound having a carbonyl group bonded directly to a carbon–carbon double bond. For example, the carbonyl absorption occurs at 1720 cm-1 for cyclohexanone, and at 1685 for cyclohex-2-enone.

Question:Benzonitrile (C6H5CN) is reduced to two different products depending on the reducing agent used. Treatment with lithium aluminum hydride followed by water forms K, which has a molecular ion in its mass spectrum at 107 and the following IR absorptions: 3373, 3290, 3062, 2920, and 1600 cm-1. Treatment with a milder reducing agent forms L, which has a molecular ion in its mass spectrum at 106 and the following IR absorptions: 3086, 2820, 2736, 1703, and 1600 cm-1. L shows fragments in its mass spectrum at m/z= 105 and 77. Propose structures for K and L and explain how you arrived at your conclusions.
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