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Chapter 14: Q.21558-14-55P (page 564)

Question: Reaction of C6H5CH2CH2OH with CH3COCl affords compound W, which has molecular formula C10H12O2. W shows prominent IR absorptions at 3088–2897, 1740, and 1606cm-1 . W exhibits the following signals in its 1 H NMR spectrum: 2.02 (singlet), 2.91 (triplet), 4.25 (triplet), and 7.20–7.35 (multiplet) ppm. What is the structure of W? We will learn about this reaction in Chapter 22.

Short Answer

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Answer

Step by step solution

01

IR spectroscopy

The IR spectroscopy gives the signals of ketone as 1740cm-1 . The double bond stretching frequency comes in the range of 3300 to 3000cm-1 .

02

Degree of unsaturation

The degreeof unsaturation helps determine the number of bonds and rings, if present in the given molecule. It is calculated by the following formula:

Degreeofunsaturatio=Cn-H2-X2+N2+1

Here, X is the number of the halogen atoms.

03

Explanation

IR absorption at 1740 : C=O, 3088-2897cm-1 : benzene double bond, 1606cm-1 :ester group

NMR data: Absorptions: singlet at 2.02 (singlet, CH3 group), 2.91 (triplet, CH2 group), 4.25 (triplet, ), and 7.20–7.35 (multiplet, benzene ring) ppm

Structure formation

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Question. When 2-bromo-3,3-dimethylbutane is treated with K+- OC(CH3)3, a single product T having molecular formula C6H12 is formed. When 3,3-dimethylbutan-2-ol is treated with H2SO4 , the major product U has the same molecular formula. Given the following -NMR data, what are the structures of T and U? Explain in detail the splitting patterns observed for the three split signals in T. 1 H NMR of T: 1.01 (singlet, 9 H), 4.82 (doublet of doublets, 1 H, J = 10, 1.7 Hz), 4.93 (doublet of doublets, 1 H, J = 18, 1.7 Hz), and 5.83 (doublet of doublets, 1 H, J = 18, 10 Hz) ppm 1 H NMR of U: 1.60 (singlet) ppm.

Question: Treatment of 2-methylpropanenitrile [(CH3)2CHCN] with CH3CH2CH2MgBr, followed by aqueous acid, affords compound V, which has molecular formula C7H14O. V has a strong absorption in its IR spectrum at 1713 cm-1, and gives the following 1 H NMR data: 0.91 (triplet, 3 H), 1.09 (doublet, 6 H), 1.6 (multiplet, 2 H), 2.43 (triplet, 2 H), and 2.60 (septet, 1 H) ppm. What is the structure of V? We will learn about this reaction in Chapter 22.
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