Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C11H15NO2). F absorbs at 1730 cm−1 in its IR spectrum. F also shows eight lines in its 13C NMR spectrum, and gives the following 1H NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 16. N."ОННLL

Answered: N. "ОН Н LL

Chemistry for Today: General, Organic, and Biochemistry

9th Edition

ISBN:9781305960060

Author:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Publisher:Spencer L. Seager, Michael R. Slabaugh, Maren S. Hansen

Chapter6: The States Of Matter

Section: Chapter Questions

Problem 6.96E: Definite shape and definite volume best describes a sample of: a.I2(s) b.Br2(l) c.Cl(g) d.F2(g)

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Reaction of aldehyde D with amino alcohol E in the presence of NaH forms F (molecular formula C₁₁H₁₅NO₂). F absorbs at 1730 cm⁻¹ in its IR spectrum. F also shows eight lines in its ¹³C NMR spectrum, and gives the following ¹H NMR spectrum: 2.32 (singlet, 6 H), 3.05 (triplet, 2 H), 4.20 (triplet, 2 H), 6.97 (doublet, 2 H), 7.82 (doublet, 2 H), and 9.97 (singlet, 1 H) ppm. Propose a structure for F. We will learn about this reaction in Chapter 16.

Definition Definition Organic compounds that have a carbonyl group, C=O, as their functional group. The carbonyl group in aldehydes is placed at the end of the molecular structure, which means the C=O is attached to one hydrogen atom and an alkyl group or a benzene ring. Just like all the other homologous series in organic chemistry, the naming of aldehydes uses the suffix “-al”. The general molecular formula is C n H 2n O.

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Step 1

The structure of F formed from the following conversion has to be proposed:

Step 2

The product forms in the reaction in the aromatic substitution reaction:

Step 3

The Chemical shifts are

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